The initial tryst.
I know, it's a cliche... but, y'know. I liked it.
I had been eighteen for about two weeks when I first laid eyes on her. Her name was D, a woman I had met in an AOL BDSM chatroom a few weeks before. She was in her early thirties, a mother [although they lived with her ex-husband in another state], and had been a lifestyle domme for much of her adult life. She was a larger woman, although her face held within it an interesting mix of charm and severity. Chestnut brown hair fell down to her middle back, and dark eyes peered out in scrutinous appraisal beneath her light brow. I would see some of the former that evening, but the latter would predominate the rest of our relationship over the next eight months.
As I said, I was young at the time, and although I had dated once or twice in high school, I was most definitely unlearned in the ways of women. BDSM hadn't been a lifelong fascination of mine, but I discovered a few months before D and I met, and it was certainly a captivating concept. I saw it as an opportunity to learn about myself, and to explore sexuality in all its facets.
We had met a week earlier, she came out with a friend of hers to have dinner with me and gauge just what she was getting herself into with this kid. I suppose it went fairly well, I wasn't really experienced enough to show any woman a nice dinner, but apparently she was pleased with what she saw because the next week she booked us a hotel room across from the mall and came to pick me up. I had to throw up a bit of subterfuge with mother, I knew she wouldn't approve of the vast age gap, but she didn't ask any questions, so off I went.
D and I had talked on the phone about the things we enjoyed sexually [or, at least, the things I was willing to try], and so I had a fairly good idea of what I was walking into. Or, so I thought. I also told her a little white lie and said that I wasn't a virgin; dishonesty isn't a typical trait of mine, but at the time I remember being terribly ashamed at my lack of experience, and I felt as though she would think less of me. That was a naivete on my part; in retrospect, it probably would have turned her on.
So we liasoned on in front of my house and we drove to the hotel in silence. She was dressed all in black, as I came to learn was her style, and I had thrown on the nicest nylon button-up top that I had and some slacks... which, at the time, wasn't very much to brag about. We walked in and I meandered my broke ass around in the lobby while she paid for the room. There was a bar adjacent to the lobby with live music, and so we adjourned there to grab an early dinner and some drinks. She did, at least, I was too wound up with anticipation, although I was doing my best not to show it.
I remember that she ordered hot wings and some kind of mixed whiskey drink. I'm sure I could have used this opportunity with an older person to indulge in a little underaged drinking, but I didn't. That wasn't why I had come. She tried to order me food as well, but I declined. The band was kicking, I recall, some guy in a zoot suit and hat whaling out covers from Cherry Poppin' Daddies. She saw that I wasn't eating, looked me up and down, and said, "Fuck it, let's go upstairs."
She went. I followed.
The room was nice, it didn't have a television but it was big, with what seemed like a mammoth king-sized bed and a radio directly across. I futzed around with the stations, and, failing to find anything sexy, was forced to settle on some classic rock n'roll station [I remember that Queen's "Another One Bites The Dust" was playing when I first entered her].
I was squaring the room away when she told me to lay down on the bed, on my back. I was surprised by it; positioning myself supine on the side of the bed, it still didn't feel real. She crawled across the bed like a predatory cat, unbuttoning my trousers and pulling them slowly down to my knees before casting them to the floor below. My erection at this point had gone from standby to supernova, and it towered there before me filled with what had to be a quart of blood, diamond-hard, ready to fulfill its purpose.
You could say she seduced me that night, she was very gentle with me, careful not to frighten me away. That would end, of course, with our successive encounters as she showed me what D/S was really about, but that night she touched me softly, like a whisper, and it was exquisite.
My cock disappeared into her mouth, and for the first time I was engulfed with a warm pleasure which sent tingles up my spine. It didn't feel the way I thought it would, it was... well, real. She worked her cock between her lips, expertly combining both hands with hard sucks and licks up and down my shaft, driving me wild. I was writhing in bed beneath her while she took me, conquered me, playing my body like a marionette.
Letting my engorged prick pop out of her mouth, a line of spittle limping between it and her lip, she cast a look up at me and rolled over onto her back, in the middle of the bed. Understanding, I took up my position between her legs, and slowly slipped her skirt down her legs. She had to help a bit with the buttons, I'm embarrassed to say, but soon they were off and once I had removed her panties as well, I had my first eyeful of the bared feminine pubis, that most precious of delights that men have killed and died for since the beginning of time.
Her pussy was shaved bare, and although these days that isn't a very big deal, this was in the nineties and it was something that, even in porn, I had limited exposure to. I laid there, propped up on my elbows, and stared at her crotch. She had large, pink lips, with the faintest trickle of lubricant seeping from her hole, and I was enraptured. I leaned forward and took a breath, taking in her musky scent, before I began licking about her outer labia and pelvis. I took my time, kissing every bit of her before delving into that rosy vortex, where I lost myself. I sucked greedily at first, but before long she began piping up with instructions, telling me how she liked to be licked and where, what to do with my tongue... Very considerate of her, because I welled up with pride when she began bucking up against my face, grabbing my hair and screaming with the force of her orgasm, her cum flowing into my mouth, an aphrodisiac which had me more aroused than I'd ever been.
Then she did something that I'll never forget, probably birthing one of the fetishes which I continue to obsess over. She rolled over onto all fours, lowering her chest to the bed.
"Lick my ass," she commanded in dulcet tones.
Slowly, I pried the fleshy cheeks of her ass apart and peered at her asshole, peering up at me, a swirl of cinnamon amidst a sea of white. Again I tried to work my way there slowly, but I found the absolute filth of what I was doing to be overwhelming, and before long I had buried my face between those cheeks, trying my best to cram my tongue into her rectum, licking and slurping away like there was no tomorrow. She had to drive for about ninety minutes in order to pick me up that day, so she was a bit ripe down there, but I didn't care; I was a man possessed. I tongued her rosebud for what seemed like forever before she rolled over and pulled me close to her.
"No one has ever done that before," she said. I gave her a confused and asked if she was serious. "I've had my ass eaten before, that isn't what I meant. I was talking about your enthusiasm... you absolutely love it, don't you?"
"Yes."
"Well, I want you to know that I'll never return the favor. I'll never lick your ass, do you understand?"
I did.
"But..." she said, her eyes narrowing playfully. "This certainly won't be the last time I allow you to please me like that. Now, my pet," she said, referring to me for the first time by the name I would come to be known as, "It's time. Are you ready?"
I was indeed. I stripped off what remained of my clothes, and psyched myself up for the coming intercourse... although that wasn't what she had in mind. She didn't know that was what I was looking forward to, you see, and she was in fact excited about something she had casually broached to me in a telephone conversation a week ago. I didn't know it yet, but it was one of her major fetishes.
"Lie down on your side, it's better that way," she said. I was still unsure of what she had in mind, until I saw her dig into the bag she had brought and emerge with a dildo, followed by a harness. Understanding now, I became afraid. Yes, this is something we had spoken about, but at the time it all still didn't feel real to me, and I never thought it would actually happened. She fastened the device about her hips, then squirted some lube onto her palm before gingerly applying it to my terrified asshole and the plastic invader she was plotting to use against me.
She came up behind me and, carefully, guided the uncomfortable dong into my anus. I clenched; unprepared, I squealed with displeasure, and she slowed down, rocking me back and forth against the strap-on, lovingly working the head of it into me before burying about half of it inside me. Gradually I got used to it, but she never managed to immerse it completely into me that night. Sensing that I couldn't take it, she withdrew from me and set the strap-on aside.
Of course, that wouldn't be the last time she fucked me, and slowly I became accustomed to it, although I never loved it the way she did. She taught me the love of the prostate, though, which is something I'm thankful for; I'm not into men, never have been and don't plan on it, but you've got to be numb to not understand the incredible pleasures which come from a prostate-induced orgasm. She took me like a bitch that night, and would do so again, but it laid the groundwork for a fascination in BDSM which would take me from the scared submissive to the confident master, although never over her. I'm glad I had the chance to truly see both side of the spectrum with someone as skilled as she was, because to this day no one's ever dominated me the way she did, it all came perfectly natural to her.
Her fetishistic lust sated, it was time for the main event. Having already experienced so much in such a short span of time, I remember little of my first moments inside her, only that it was wonderful and that before long I was pounding myself into her and we were screaming. I didn't cum early, though; we went for a good hour before I exploded semen into her womb, and it was only ten minutes of pillow talk before I was rock-hard yet again and back inside her.
We fucked and fucked for hours, stopping only once to order room service, before I plowed into her again. At eighteen, I was popping hard-ons every fifteen minutes, and I put my youthful libido to maximum effect that night. Both us and the sheets were drenched in perspiration by the time we had finished, and I collapsed into her arms and enjoyed one of the best nights of sleep I can remember.
Wow, that story was longer than I thought... but Jesus, what an incredible experience. I fell in love with sex that night, with the carnal wisdom of the older woman, the hourglass figure, the game of giving and taking power in the bedroom... and, of course, with the ass of my then-Mistress. She would take major advantage of that fetish later in our relationship, offering me a taste of her if I would only endure some heinous torture for a little longer... but, all of that is another story.