The Dark Portal

Everything in these memoirs happened, although I will admit real life was often slightly less... um, pornographic. They develop slowly, though, so if you're looking for something designed to get you off in three minutes you've come to the wrong place.

Writing about one's own life is in itself a form of masturbation, but masturbation is fun. Writing these dirty stories brought back many things and even people I had forgotten.

Their names and the places have been changed, because in cyberspace you never know who's looking over your shoulder.

I hope you have as much fun reading these stories as I had writing them.

-- Felix

I absolutely love women's asses. If I were an evil emperor I would have women with beautiful butts come in at bedtime so I could use their asses for pillows. All sizes and shapes are fine, except flat.

And I know it's irrational, but the asses have to be female. One proof to me of my own heterosexuality is that in my more athletic years, when I was often in shower rooms full of naked males, I was not aroused. And this was in the days when a glance from a woman could give me a hard-on in a physics lecture.

No, it's female bottoms that do it for me. I've outgrown my teenage obsession with breasts, and after seeing thousands online I even became bored with pudenda, shaved or regular.

But I have never tired of asses. I love the look of them, the feel of them, the way they hide that wonderful little target, and I even love the smell and taste. I will admit that, for me, diving into an asshole is more fun if it's squeaky clean.

The anus stopped being too dirty to think about in the summer before I started college. The Danish cousin of a friend, slightly older than I was, came for an extended visit, and somehow she and I ended up with a movie date. When I went over to pick her up, I found that the two of us had the entire house to ourselves, which meant it didn't take long for us to start comparing our nations' underwear styles.

Unlike most young women of that era (the Pill was still a news item), this cousin was eager to fuck and ready to experiment. And she was more experienced than I. The thing I remember most clearly was her insistance that fucking is better if each of you has your partner's finger up your ass, particularly during orgasm.

And then she proved it, changing my understanding of sex for the rest of my life. I had never had a parter who would let me anywhere near her asshole, much less touch mine, but here was a woman who wanted mutual penetration.

From then on, I was always in search of that little pucker, and here are some of the women who enjoyed it.

Samantha

Anal sex has been rare enough in my life that I can still compare the experiences. Samantha is the first to come to mind, because she was genuinely enthusiastic about anal play, and talked about it easily. She enjoyed having tongues and other things up her ass, but within limits--and those limits didn't include a raging boner. She tried hard--twice--to give me her other flower, but she clearly didn't enjoy it.

(In all honesty, I doubt that any of the women who offered me their windward passage ever really "enjoyed" it, although there were a couple who probably would have if I had known better what I was doing. My reviews ranged from "It's intense," to "My bottom hurts.")

Samantha was so small and slim even in her mid-twenties that I could carry her in my arms. She had tiny breasts, but her nipples were very expressive, and her ass was what you would call compact. She was pretty all over, with dark hair that fell straight to her waist, and her mount of Venus was prominent, with a tuft of straight pubic hair on the crest, like seagrass on a little dune.

And she had no problem with me playing with her asshole. In one of my favorite positions for foreplay, she would get on top of me, up on her knees in a sixty-nine position. It allowed her to be in charge as she sucked me, and she would drop her ass toward my face so I could lick and suck not only her almost hairless little pussy, but also--especially--her ass. I spent a lot of time in that position. I would try to fuck her little brown knot with my tongue, but all it did was give me a tired tongue. She liked it, though, and she would do it for me, too.

On a few occasions when we were languidly fucking and I found myself unable to come, even when she was way past being satisfied, I would ask her to put her finger up my ass. She didn't hesitate. In fact I think she enjoyed it. It also worked every time.

And in a moment that was memorably perverted, we once did a sixty-nine with our legs drawn up so we could tongue each other's assholes. It was interesting, but I have to report that I didn't find it particularly erotic. Maybe it was too much work, or maybe the idea was better than the reality.

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One evening we were sitting facing each other in the bathtub, relaxing in water as hot as we could stand it. Somehow I got my foot under her bottom in such a way that my big toe was wedged into her asshole. I didn't even realize at first what was happening. The big toe isn't exactly sensitive. But she closed her eyes and opened her mouth in a way that I recognized. She was enjoying the sensation! So I pushed and wiggled my toes, and she smiled at me.

I remember kissing her in the bathtub with a finger up her butt, and the next thing I remember was grabbing a bottle of baby oil from the medicine cabinet as I followed her into the bedroom.* She had said nothing, but "anal" clearly was being offered, and I was quite excited.

Back in my college days I had twice experienced the intensity of pushing my cock into a willing girl's asshole, on one occasion lasting maybe ten seconds, and on the other realizing immediately that my poor partner's rectum was too dry for penetration, but it didn't matter because I was already coming. Oops.

But by the time of the bathtub incident, I had done some reading. Not enough, but I did know that her sphincter had to be relaxed and we needed some sort of lube.

I tried to get Samantha to stay on her knees with her tiny ass in the air, but she wanted to lie on her stomach. It's possible she was embarrassed. At any rate she lay on her stomach and parted her legs, allowing me to push my oil-covered little finger into her butt.

It slid in without resistance, and I wondered how it felt. She seemed to be all right with it, and I was afraid to break the spell.

My plan was to keep using bigger and bigger fingers and then my thumb before the main event, but she wasn't relaxing and again I think she was embarrased by the whole procedure. As I began to use two fingers, she said, "Tom, just go ahead," and I did. I remember that entry seemed imposible. She was so small, and she kept clenching. I slopped as much oil as I could on my cock and her anus, then I started to push and she pushed back, until finally the head popped inside. It was like being grabbed by a fist. I began very slowly pushing on in. It was clearly uncomfortable for Samantha, but she told me to keep pushing.

You couldn't really call what we did "fucking," but that might be because I didn't last more than a minute or two in there. She was so tight, and I was so turned on by the very idea of fucking my sweety's little brown asshole.

Samantha was the one who said, maybe twenty minutes afterward, "My bottom hurts."

In spite of that, we discussed it and she actually let me try it again on a second occasion, armed with knowledge gained from various hippie feminist journals like "Our Bodies, Ourselves."

The second time was a little better for her, as I remember, but again it was brief--maybe three minutes rather than two--and Samantha for sure was doing it not for fun but for me.

Afterward, I asked her if her bottom felt all right. She said, and I quote, "I guess there are just some places man was not meant to go."

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* You young men who haven't had the opportunity to penetrate the dark portal should know that you almost always need lubrication. Oil is not what you want, and petroleum jelly is not much better. A water-soluble lube such as K-Y--and lots of it--is the thing. And if you have any time to plan, warm the lube container up in a bowl of hot water. That stuff is always cold, which doesn't help.

And as long as I'm giving advice, do not be fooled by videos in which cocks magically slide into women's--or men's--assholes. Those people have pre-stretched and greased themselves. If you don't believe me, I suggest buying a dildo that's at least as big as your cock and trying to push it into yourself quickly. Anal can be very unpleasant if you rush it.

But If you don't rush it, it's fun both to give and to receive. Samantha was wrong.

Janice

Janice was another woman who was far more than just a notch on the bedpost. If we had committed ourselves to becoming a couple, though, I doubt that we would have lasted long. For one thing, she was quite intelligent and had a background in psychology, so she recognized my games--I didn't even know they were games--and took no shit.

We were housemates. When we met, we each already had a partner, and she was not inclined to flirt. But I was drawn to her. She was smart, funny, and exotic, with jet-black curly hair, golden skin, and pillowy "bee stung" lips. Her dark eyes were framed with heavy lashes. All this without makeup.

As time went by, we became good friends. Over a couple of years each of us lost our romantic partner, dated other people, and generally became old shoes. Intellectually we were very compatible.

We were always aware of each other, though, and because this was a college town in the era of commercial hot-tub and sauna joints, we had been naked together several times. With several other people in the room.

(I always pretended to be unimpressed by the close presence of five or six naked women in the room with me, but I loved that "college hippie" era. Bodies everywhere I looked. My, my. I'm grateful to have been alive. Theoretically, it wasn't about sex, but yes it was.)

When Janice and her boyfriend were breaking up, he began to leave for one reason or another for days at a time, and it was during this period that she asked me one evening if I would give her a massage. Along with various supposedly healthy "cleansing" activities, such as fasting and enemas, massages were all the thing, not necessarily intended to be sexual. So I tried to act cool, rather than exited, as I said I would be happy to help.

When she called me into her bedroom, she was just out of the bath, wearing a thin cotton shift. I was wearing the standard 70s uniform of T-shirt and jeans. The room smelled like incense, and was softly illuminated by a couple of candles. I could see that she didn't just want a quick back-rub. She wanted the spa experience.

I knew enough about massage to help her arrange herself properly, spine straight, on her stomach. She didn't want me to use oil, which made sense because she and her bedding were both clean, but I was a little disappointed. Few things look sexier than an oily body.

I straddled her with my weight on my knees, and began to slowly loosen up her core muscles by simply leaning heavily on her shoulders, back, and hips. Then I started doing the muscle groups with my fingers, digging deeper (faux-Swedish massage), as she got used to it.

Doing her back through the shift wasn't satisfying, though, and eventually I found myself running my hands under the flexible neckline of her shift to get at her skin. She raised up, pulled the entire top of her flimsy outfit down to her waist, then lay back down. I remember how beautiful her skin was in the candlelight. Her dark little nipples had been erect, and I was working on a painful erection of my own.

I used what knowlege I had of massage to give her torso, shoulders, and arms what I hoped was enough attention, then turned south. When I started working her amazingly strong ass muscles, and again reaching under her shift, she raised her hips and held the pose long enough for me to get the message. I pulled her entire garment down her legs and off.

I started to resume my position on top of her, but realized that my jeans probably didn't feel great on her bare skin, and they didn't feel so good to me, either, so I got up and let them drop to the floor, keeping my boxers on because, after all, this wasn't supposed to be about sex.

That message was still failing to reach my cock, though. As I straddled her on my knees, this time facing her feet, I lowered my weight gently onto her lower back. My underwear was holding my growing bulge down, and I was afraid she would feel it rubbing her, so I pulled Little Tommy up through the gaping fly of my boxers and freed him to wave unencumbered. She was face down with her eyes closed, so what the hell. As far as she knew I was just sitting there in my boxer shorts.

It was at that point that the massage became an intense teasing session. Her ass, full, firm, and golden, had always impressed me as she ran around the house in knit dresses that amounted to long T-shirts, and now here it was in front of me by candlelight.

I began by gently working her sides, just above her hips, then moved to her wonderful collection of glutes: maximus, minimus, and so forth. As masseur, I had free rein to play with her ass, and I took it, clutching and pulling on her butt cheeks and pushing my fingertips in a businesslike way into her cleft without ever actually touching her anus. I leaned over and gently moved her legs farther apart, studiously avoiding her crotch. I then worked my way down her golden thighs, inside and outside, while I feasted my eyes on her very dark and interesting asshole. Her generous mass of black pubic hair hid her pussy, but I knew it was there and so did she.

After I worked her calves, I did my best to dig into her feet without tickling her. She was grunting along with my efforts, and sighed a couple of times as I roughly stretched her toes.

She was breathing deeply as I climbed off her legs and stood beside the bed. I tried to tuck my erection back into my underwear, then helped her turn face-up. Again I got her arms and legs arranged.

I pretended not to look at her body as I climbed back up onto the bed, and she pretended not to notice my ridiculous erection. Little Tommy popped right up through the fly, but her eyes were closed.

This time I separated her legs right away in a no-nonsense manner and straddled one of them, so that I wasn't sitting on her hips.

I leaned over her and worked downward from her neck and shoulders, digging slowly into her deltoids and moving down her arms. She began breathing hard again as I rolled her biceps and triceps firmly, and she started grunting as I pushed my thumbs into the palms of her hands.

When I pulled gently but firmly on her fingers, one by one, she opened her eyes and looked directly into mine. I smiled and put her arms to her sides in a meditative position. She closed her eyes again without either of us saying a word.

Now I began to manipulate her pectorals, digging closer and closer to her breasts without actually grabbing them. Her breasts, like the rest of her, were golden and perky, and she had wonderful dark, narrow nipples. They grew longer as I worked near them. Her aureoles were small and brown. I watched her nipples as my hands went all around them. Then I scooted my butt farther toward her feet and began manipulating her abdomen and the front side of her hip muscles, pushing downward toward her mound.

I thought it would be a bridge too far if I actually massaged her pussy, so I kept moving down her legs, giving a great deal of attention to the inside of her thighs.

Janice was no longer breathing hard, but her chest and face were flaming red.

I moved up and planted my bottom on her upper thighs, with my cock hanging out over her mound, and I went back to her pecs, gently massaging everywhere except on the business end of her breasts.

I ran my hands down her arms and sat up, and she opened her eyes again.

"That's about it," I said. I started to get off of her, but she grabbed both of my hands and planted them right on her breasts.

"Don't go," she said.

I took one of her hands and kissed her palm, then moved it to my cock. I leaned down and took a nipple into my mouth. Now I was glad we had skipped the oil.

"You have wonderful nipples. I've always wanted to do this," I said.

I rolled off of her and lay down next to her. We held each other's faces and kissed, languidly and seriously.

"I've always wanted to do this," she said.

I went back to her breasts, taking turns with them, then started kissing my way down her stomach.

"Wait!" she said, and rolled off the bed. She stood beside me and pulled my shorts off, looking at my urgent erection while she gently played with it, then turned and blew out the candles.

"Hey!" I said. "I want to see you."

"You've already seen me. I don't want to burn the place down," she said.

I think she was just shy enough that she didn't want to show off her most private parts.

My eyes hadn't adjusted and it was pitch black, but I could feel her and smell her, and once she was next to me again I went back to what I had been doing. I quickly began tonguing and sucking her very wet pussy. She groaned. "Thomas," she said. I pushed her legs open wider, and held them there as I lapped at her.

"As long as I'm here," I thought. Pushing her legs up and back even farther, I dipped lower, licking her remarkably pliable anus. I was able to push my tongue inside without much effort, and I essentially fucked her ass with my tongue for a minute.

As I pulled my head away and let her legs fall back into a more normal position, I felt her hands under my own. I was confused for a second, then realized she had been holding her ass open for me! No wonder it had been so easy.

I laughed. "You like that?" I said.

In answer, she got up on her knees and turned around, offering me her ass in a way that could not be misinterpreted. She fiddled around with the bed pillows, arranging them so she could prop herself up on them, and I began to think she might have done this before.

I licked and played with her ass for a few minutes, then crawled up and offered my cock to her face. "Make me wet," I said. "Spit on me." She took me in her mouth and made slobbering sounds as she assured wetness. I almost came right there. I bent and kissed her, with my face all wet.

"You smell like my ass," she said.

"I like the smell of your ass," I said. And I did.

Behind her again, I began trying to hit my mark between her cheeks without being able to see it. Once I knew I was in the right place, I began to push, but she was no longer yielding.

"It's too tight," Janice said.

By this time I knew what to do. "Bear down like you're taking a shit," I said. So she pushed at the same time I did, and I popped in.

There in the dark I slowly tried to work farther into her, but it wasn't lubricated enough. For a while the two of us just rocked in place, with her gripping my cock like a vice. "Go ahead and come in me, Tommy," she said, and thrust herself back toward me. "Go ahead. Come whenever you want."

That's all it took. By the time she had finished saying it, I had lost control. I came hard! We both made some noise. We fell over sideways and I stayed in her, with her wonderful ass tucked against my groin and my hand on her breast.

Neither of us said much. I don't know what she was thinking, but I was wondering if this had been a smart move.

The only thing she said that I remember was, "That feels weird," as my shrinking cock pulled slowly out of her bottom and finally popped out.

We snuggled for a while, but I'm pretty sure I went back to my own bed before long. Maybe she kicked me out, because I don't remember seeing her in the morning before she left for work.