Jill's Journeys
Chapter 1: Jill's Journeys

Caution: This Coming of Age Sex Story contains strong sexual content, including Ma/Fa, mt/Fa, Fa/Fa, Lesbian, BiSexual, True Story, Incest, Group Sex, Water Sports, Cream Pie,

Desc: Coming of Age Sex Story: Chapter 1: Jill's Journeys - People can come of age twice, once as a kid and once when they know what they want. In this story, I and others come of age in polyamory, with a creative and sexy group of people. Rather than being fucked by lawyers, we happily fuck them, as well as other interesting people, in the Star Trek Infinite Diversity of Infinite Combinations, in search of the best human potential of Abraham Maslow.

“A musician must make music, an artist must paint, an poet must write, if he is to be ultimately at peace with himself. What a man can be, he must be. This weed we call self-actualization ... It refers to man’s desire for self-fulfillment, namely to the tendency for him to become actually in what he is potentially: to become everything one is capable of becoming.”

Abraham Maslow

Had Jill Ohman’s mind stayed in the same path as when I met her, I suspect we’d be happily married. She was among the few people who might have convinced me to be a parent, because I loved her, even though I did not love children. Nevertheless, she will always be part of my life. I can love her, but, for a time, was not in love with her. Today, we keep reevaluating and redefining our feelings, in a good way.

Of Swedish heritage, she was tall, perhaps 5’8”, not unduly slender but with no excess weight. She enjoyed lying in the sun, first because it felt wonderful, but that it also bleached to a glorious gold, complementing her ice-blue eyes. Jill tanned deeply and well. When she took off her clothes, the tan lines were emphatic and erotic.

We met at a New Age human potential movement course. My ex-wife, Camille, with whom I was by then friends, introduced us. Jill came to the Wednesday through Friday evening sessions straight from work. As a technical writer, editor, and instructor, she wore a dress-for-success style. Her favorite outfit was a camel-colored suit with a blue oxford shirt, but she also liked Harris tweed, occasionally a black suit, and sometimes power red.

Eventually, I noticed that the gold chain around her neck was not simple decoration, but something was suspended from it. “Is that a religious symbol around your neck, Jill?”

“Not in the usual sense, but I do think of it as a spiritual symbol. It’s Maslow’s Hierarchy of Needs, with self-actualization at the top. Self-actualization, sometimes called a peak experience, is on top. It’s the state in which I want to spend my life:

  • Self-actualization

  • Esteem

  • Love/belonging

  • Safety

  • Physiological

Jill looked sad. “So much of the time, I don’t get above the level of safety.” Very softly and gently, she touched my face. “Maybe we can climb some of the pyramid together.” She sniffled slightly. I sensed intense longing.

If it wasn’t too warm, she preferred knee boots with a moderate heel. The boots set off some of the finest thighs that I’ve ever admired, hiding slightly thick ankles. When the weather permitted, Jill liked to walk three miles to work, definitely firming up her legs. On the weekend casual days, she wore flattering stretch jeans.

Since I worked from home, near her office, we began meeting for lunch. Jill was a superb conversationalist, although I did not ignore her lovely face and hair, nor the shapely legs that, seated, her skirt rode up above her boots. For most workdays, she wore no makeup, but, after a couple of lunches, added a bit of lipstick and mascara. I sensed that makeup was something was a courtesy, perhaps a gift, to me.

At our first lunch, I was impressed by the intensity of our eye contact. It was quickly obvious that she was expert in space technology, but we drifted into the romance of older technologies.

“To Scots engineers.”

Lord, Thou hast made this world below the shadow of a dream,
An’, taught by time, I tak’ it so - exceptin’ always Steam.
From coupler-flange to spindle-guide I see Thy Hand, O God
Predestination in the stride o’ yon connectin’-rod.
John Calvin might ha’ forged the same - enorrmous, certain, slow -
Ay, wrought it in the furnace-flame - my “Institutio.”
I cannot get my sleep to-night; old bones are hard to please;
I’ll stand the middle watch up here - alone wi’ God an’ these
My engines, after ninety days o’ race an’ rack an’ strain
Through all the seas of all Thy world, slam-bangin’ home again.

“Howard, I really like the way you look into my eyes as we talk. It honors me to have you have such a focus on my mind.

“I talked with Camille, and she encouraged me to be very frank with you. She said that both of us have some needs and desires that might shock other people, but, at worst, I might simply choose not to do something, or vice versa. Camille told me that you’re horny as hell, in the nicest way, but you’ll never take liberties. So, let me clarify something...” Jill pulled her chair back from the table, half-stood, pulled her skirt very high on her legs, and sat back down with a brilliant smile. “I like being physically admired. In this outfit, this is about all I can show off at the moment, but please enjoy my legs until I can show you more.” She wiggled again, and I felt her shoe running up my calf.

“For details, let’s wait until we can do something about it. But from what Camille tells me, and my imagination, at the very least, we both like some leg-related games. They just may be games where we haven’t gotten much satisfaction.

“I’m really sorry, but I have to get back to work. It is Friday, so we can have the weekend. You know that I usually walk to work. Pick me up after work. We’ll have dinner at my place--I’ll have an assortment of munchies so we can graze.” She paused. “Not making any specific suggestions yet, but why don’t you bring an overnight or weekend bag, just in case?

“Camille told me that you really, really, want a woman to be frank, and that it confuses you when you have to guess at signals. Believe me, I’m being incredibly frank -- I’m taking risks like hell. Is this what you want?”

“Oh yes. Oh yes.”

She took my hand. “I like you looking at my body, but I adore the way you look into my eyes. The first is at Maslow’s lower levels, maybe at love, but the latter moves higher, into true esteem.”

The perfect response struck me.

It was many and many a year ago,
In a kingdom by the sea,
That a maiden there lived whom you may know
By the name of Annabel Lee;
And this maiden she lived with no other thought
Than to love and be loved by me.

Jill picked it up,

I was a child and she was a child,
In this kingdom by the sea;
But we loved with a love that was more than love-
I and my Annabel Lee;
With a love that the winged seraphs of heaven
Coveted her and me.

With our eyes locked, I continued

And this was the reason that, long ago,
In this kingdom by the sea,
A wind blew out of a cloud, chilling
My beautiful Annabel Lee;
So that her highborn kinsman came
And bore her away from me,
To shut her up in a sepulcher
In this kingdom by the sea.

Were there tears in Jill’s eyes?

The angels, not half so happy in heaven,
Went envying her and me-
Yes! - that was the reason (as all men know,
In this kingdom by the sea)
That the wind came out of the cloud by night,
Chilling and killing my Annabel Lee.

We began to chant together.

But our love it was stronger by far than the love
Of those who were older than we-
Of many far wiser than we-
And neither the angels in heaven above,
Nor the demons down under the sea,
Can ever dissever my soul from the soul
Of the beautiful Annabel Lee.

For the moon never beams without bringing me dreams
Of the beautiful Annabel Lee;
And the stars never rise but I feel the bright eyes
Of the beautiful Annabel Lee;
And so, all the night-tide, I lie down by the side
Of my darling- my darling- my life and my bride,
In the sepulcher there by the sea,
In her tomb by the sounding sea.

“Jill, as much as that moves me, my Vulcan side makes me wish that Annabel’s lover had some appropriate antibiotics on hand. I’d prescribe azithromycin and levofloxacin.”

Jill laughed in delight. “Me too. Me too. You and I really need to explore Vulcan lust. Why can’t humans always have pon farr?”

At her apartment, Jill excused herself, and went into what I saw was a walk-in closet and dressing room. When she came out, I was to know that she enjoyed my looking at her.

Rather than her business conservative camel, navy, or tweed, she was a vision in white, which set off her deep tan. Her shirt still was buttoned, but sheer. I could see a soft darkness on her chest. Below it, however, was an extremely short skirt, displaying her tanned legs and what must have been five-inch heeled sandals. “This is the first course, dear.” She gestured to the couch, waited for me to sit, and then posing. Jill came over and sat on my lap, facing me.

“Let me share a little about myself. I guess I’m in that category of spiritual, not religious. If I have a deity, it’s the humanistic psychologist, Abraham Maslow.

“When we talk about many psychologists and therapists, like Freud, the focus is on what is wrong with people, and how to fix emotional illness. Maslow was less about fixing and more about being the best we possibly can be. He called that peak state self-actualization.

Self-actualizing people enjoy life in general and practically all its aspects, while most other people enjoy only stray moments of triumph.

Abraham Maslow, Toward a Psychology of Being

While I was a little hesitant, I put my hand on her thigh and started to stroke. She sighed. “Oh, yes. Kiss me, you fool.” My lips met hers, to which she responded first with a tongue flicking between them, and then a fully open mouth. Our arms, unbidden, wrapped around us. She slid a knee, gently, between my legs.

“I have never been this explicit, but what I’m doing, I think, is good for both of us. If you haven’t noticed yet, I’m wearing a thong. I’m not doing that to hide anything from you. Push it aside if you want to feel my pussy.

“But I have what may be an unusual way to masturbate. I like to pull some cloth tightly against my pussy, and then rub.”

From under the bed came a somewhat indignant “rrowROW!”

Jill laughed in delight. “Oh, I see I need to disambiguate pussies.” She bent, reached, and brought out a large black cat, looking dubiously at me, but clearly comfortable in her arms. “This is Spook. It’s a good sign that he isn’t running away just from your presence.”

Very carefully, I extended a hand, and let Spook sniff it. He head-bumped me, and I explored, finding a spot behind his ear that was fine scratching territory. From there, I went to That Spot in front of his tail, and scratched there. He frantically licked my arm, then fell onto his side, rolled over, and presented his belly. I stroked him in what seemed to be a very good place.

“I am impressed. He usually hides from strangers.

“Howard, I hope you are OK with my directing the event. I’m not trying to be dominant. I’m trying both to be sure that some of our individual desires and fears are honored. For example, please don’t penetrate my orifices until I’m ready for that.

“Camille may or may not have said anything about it, but a good deal of my sexual experience is with women. That may wind up being my preference.

“On the other hand, I hope for sex to me a Maslow peak experience. There have been rare occasions where really good sex puts me into a wonderful alternate reality. It’s more than a great orgasm. That happens only every few years.”

I laughed. “Mine, too. Uh, like most guys that are honest about it, I’ve played with guys at camp and such. It’s not my focus. I have thought quite a bit, though, about scening with both sexes.”

“Some things might be a long way off, but I promise that you won’t leave here unsatisfied.”

“I believe that, dear. It sounds like there are some things that both of us like yet rarely can experience.”

“Yes. For those, we need sustenance.” Gracefully, she rose, and with a pleasantly exaggerated swing of her hips, she went into the kitchen. Jill returned with a tray of sushi, a pitcher of orange juice, and several bottles of beer.

“First, drink some orange juice.” I complied, but was puzzled. “Now, I’d like you to take off, at least, your pants. I’ve got robes if you like. Why do I ask? I want to have skin-to-skin contact for the length of our legs. You’ll notice I didn’t put on any hose. My thighs are very sensitive, which is one reason that I know we can have fun even if we don’t do all the standard stuff right away.”

I wasn’t complaining. “I know that you’ve got pleasure for both of us in mind.”

“OK. Bring that armchair close to the couch. Extend your legs so I’m between your feet.” She lounged back on the couch. “Now, before Spook interrupted, I was going to show you what I do.” She put one of her heels on each of my thighs. “See my naughty shoes and how they flatter my legs?” I was entranced and excited. She grasped the straps on the panty part of the thong, and started to rub and pull the cloth against her mound. “Oh yeah. I’m teasing myself, imagining being rubbed against. It could be your face. It could be your leg, humping.” When she raised a leg, I started playing with her heel. “Yeah. Fondle my slutty heels. Get turned on for the next course.”

I was beginning to breathe hard. Jill opened her blouse, showing me small but perky breasts, with hard pink nipples evident in the surrounding tan lines. “Pull down your shorts and masturbate with me.” I reached for one of her shoes. “Yeah. Indulge your fetish.” I licked and sucked the stiletto, with Jill happily encouraging me. “Damn, that turns me on too! When you cum, spray my legs!” She clutched at herself and screamed her climax.

After that encouragement, I couldn’t resist long. Jill had an enormous, happy smile. “That was wonderful. It made both of our fantasies OK. It was a real sharing and makes me feel emotionally close, not just satisfied. I’ve got issues on sucking, but...” Her fingers scooped semen from her thigh. She hesitated for a moment, and then put them into her mouth. “The orange juice is working its way down. You’re pretty tasty.

“I think I need to explain a couple of things. At one point, I decided that I’d save fellatio for my husband. The more I think about that, though, the more I realize that I may never marry a man. That’s what I mean by having issues. As you might have figured out, I get very excited by other oral activity.

“I’ve got no fundamental objections to anal, but I hear that it can be painful unless done very well. At some time, I may be ready for that.”

I moved to the couch, slid her onto my lap, and kissed her deeply. Jill’s eyes opened wide. “I thought guys freaked at tasting cum?”

“Why? Why should I, especially if you took it out of me?”

Her arms pulled me tight. “Thank you. Wow. You just complicated, in the nicest way, my concerns about sucking. I don’t know quite how to deal with this sort of sexual respect, but it will be nice. Help me open up the couch.” We turned it into a bed. She slipped out of her shoes, and we stripped, then slid under the sheets. “Let’s cuddle, kiss, and sleep for a while. Think of it as charging batteries.”

To my surprise, we slept soundly, until the morning light woke up. During the night, I had been vaguely but pleasantly aware of Jill in my arms. It didn’t quite hit me that while she was an athletic woman of considerable size, she was unique in my experience of bedmates -- seemingly weightless. It was a wonderful, restful way to sleep.

We exchanged soft kisses. “I want to do something that’s a lot of fun with other women, and ought to be fun with a man. I just have to be careful that your balls don’t get smooshed.”

“Oh, that’s reassuring!” Instinctively, my hands moved to protect them.

“Let’s try this slowly. We both should be undressed completely.” That was soon achieved. “Lie on your back. Raise one leg so I can rub my mound against it. Oh yes.

“Now, put my other leg between yours, so you can fondle my thigh. Just find a position where it rubs against your skin but doesn’t push too deeply into your groin. It may slip in there, and I’ll be as careful as I can. When two women do this, hard leg to pussy pressure is nice.”

She started to rub against me, and lowered her face to mine. “Kiss as hotly as you can. Use your hands to play with my ass.”

“I’ve got to go pee, but don’t let me stop us talking.” She slipped into a negligee, got a funny smile, and reached into a drawer of the nightstand. “I might kill myself if I tried to go far in these, or on a carpeted floor, but enjoy these.” She put on what must have been six-inch pumps.

It was a small place, so I could easily hear her in the bathroom. She left the door open. “You can follow me.” A little surprised, I did so.

It puzzled me a little when she first sat on the toilet, without undressing. “Like my legs?”

With absolute truth, I agreed. “Absolutely.” She reached out one leg and hooked a small chair that she had placed nearby.

“Sit and enjoy”. With that invitation, I began to stroke her thighs. “Get in front of me.” She spread her legs. “Will you touch me as I pee?”

“Sure! I’ve thought of this sometimes, myself.” Her fluids were amazingly warm, even hot. I twisted to kiss her. Our tongues danced.

“That’s more sharing, Howard, riskier sharing. I’m feeling incredibly close to you. To be utterly honest, I find pee play to be another major sex act, right up there with oral, anal, and vaginal -- and it can combine with those.”

Later that weekend, sitting at the dining table, she looked into my eyes, with an expression of concern. “Howard, are you my friend?”

I had no idea where this was going. “Absolutely.” I meant it. I didn’t know if the gods would make us soulmates, but I deeply liked Jill. It was fair to say that I loved her, although I might not be in love.

“More and more, I’m thinking sexually of women. I still want some physical contact with you, though, and I hope it can be satisfying for both of us. I doubt I can meet all your needs, but maybe our future is polyamorous.

“You know that I’ve not sucked you, telling you, truly, that I reserved that for a future husband. I’m thinking that through, since I may not have a conventional male husband. I’m also tending to think of fucking as for the father of my children, but I won’t rule it out.

“Let’s go to bed and at least cuddle.” Soon, we were spooning. Jill wiggled her pantied butt at me, and I grew very hard. My cock flattened against her, between her firm cheeks.

“Oh, that is not at all unpleasant.” Her phrasing of “not at all unpleasant” was so Jill-like. She moaned a little. “Maybe I’m more ready than I thought I was for anal sex. This is exploration. Let me control the pace.

“Wait a minute.” She got up, went to her dresser, and pulled out a thong into which she slipped. “You know that I like to have cloth stretched against my pussy. You can push the string aside for access to me in back. I want you to start rubbing between my cheeks. I’m not ready to have you penetrate me there, but I’m thinking about it. I’m thinking about it a lot. I’m also thinking of some kinkier things -- not yet on those.”

Returning to the spooning position, my penis rubbed between her buttocks. While I wasn’t sure if it was sweat, or perhaps vaginal secretions that had gotten higher, she was increasingly wet and slippery. “Hold still, honey.” She reached behind, and pressed my cockhead against her opening, then wiggling a bit. To my surprise, her sphincter relaxed. It was a delicate moment. I certainly didn’t want to push and hurt her. My increasing thought was that she was preparing herself for deeper anal contact.

Jill stretched an arm to her bedside table, and picked up a tube of lubricant. “Try some on your finger. This is scary, but exciting scary. Just be slow and gentle, as I know you’ll be.” Anointing my finger, I began to work the jelly into her opening. She moaned a little and pushed back at my hand. One finger easily slipped in, and then another. Before long, I had three fingers moving in and out, her hips helping and her making soft happy noises.

“Keep doing that.” Her hands moved in front of her, and she began pressing her panties into her mound. Occasionally, her hand reached to the thong to pull it tighter against her. Suddenly, she gasped, moaned, and shook. After her breathing returned to normal, she murmured, “Try putting the head into me. I want it, but know we shouldn’t rush this.”

Reaching down, I found her to be fully lubricated, and pushed gently forward. I felt my cockhead sliding past her sphincter. “Ooh, nice. Hold it right there. I’m feeling stretched open but delightfully so.”

Jill purred, “You said you wouldn’t mind sharing? Think of what you’d see if I were licking a pretty woman as you did this!” I twitched with the thought. “Stay pressed against me while I pull and rub myself with the thong. It won’t take me long. It didn’t take me long to climax last time.” I felt the movement through her hips. Somewhat more of my penis slipped into her, and I sucked in my breath. “It’s OK, honey. You aren’t hurting me. Far from it ... oh ... oh!” She made loud and happy noises, tensed, and went boneless in my arms.

“Now it’s your turn. I know how much you like to taste me, and I’m absolutely dripping. On your back and get comfortable. I’ll slide a pillow under your head.” Jill then moved to straddle my face with her strong thighs, and leaned forward. Indeed, her juices oozed, but not as much as when I began to lap between her labia. “Play with yourself, Howard. Soon, though, I’ll be ready to do that for you. Just give me a little more time.” Frankly, it was luxurious pleasure to masturbate for my greatest pleasure, knowing Jill was eager to excite me. She sensed my breathing quicken. “Yes! I want you to climax, with me helping you!”

And so I did. In her weightless way, she dropped beside me, and kissed me into sweet slumber. Her last words were “I think Abraham Maslow’s ghost is smiling just a little.”

She absolutely was a sapiosexual, attracted to intelligence. Happily, so was I. Her elegant speech was part of her initial attraction. When her demons were at bay, she was a fine poet.

We were enjoying a drive on the border of West Virginia, and playing trivia. Space science and history was one of her serious interests. With a naughty grin, she asked, “What was John Glenn’s middle name?”

I didn’t know that I knew, but out of my lips popped “Herschel.” She gasped. In a low voice, she growled, “Find a place to pull into the woods if you see any. Otherwise, find a hotel. After that answer, I want you to take me, perhaps shouting details of the Mercury-Atlas spacecraft.” Her breathing quickened. “Yes, I want you to be my Atlas missile.”

Jill wiggled in her seat, opening her stretch jeans. “Give me your hand. Feel me getting wet.” I certainly had no objection, and let her steer my hand under her panties. My middle finger stroked between her labia, caressing her clit as I withdrew my hand. Smilingly, I tasted it.

Of all the women I have known, Jill had the most delicious secretions. She reminded me of sweet cream.

“Bless us, Maslow! Get in the back seat.” She opened my pants, yanked down her jeans, turned her back to me, and plunged onto me, in reverse cowgirl. Jill chanted, as if invoking a primitive god, “Peak experience! Peak experience!”

When we returned to her apartment after that, she took my hands in hers. “Thank you, Howard, for having spent a little time with me at the top of Maslow’s pyramid. I hope to do it again and again, but even once is memorable.” She went to her jewelry box and withdrew something, which proved to be a pendant like hers. “May I put this around your neck?”

“My darling, I am deeply honored to accept the pyramid.”

Jill had had social isolation in the past. Her brother, Jack, had frank schizophrenia, which disabled him.

She started to show symptoms beyond isolation, moving into hallucinations. When she stayed on medication, she stayed charming and effective, but when she didn’t take her antipsychotic, she could agonize about being followed. I remained one of her anchors. Still, I was amazed at her core strength. When her concentration was impaired sufficiently that she could not work professionally, she was an effective waitress and moved to a nice but affordable apartment. She still managed to meet Maslow’s physiological and security needs.

She began calling me late at night, talking about being followed. It wasn’t in a plausible way, but involving messages in license plates, and people around her blinking in code. It tortured her to see things that were invisible to me.

I’m quite comfortable in saying that I love Jill, but when she’s crazy, I’m not in love with her. I continued my social life, but Jill was never far from my mind, as an intriguing friend.

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