Sunday, June 16, 1974.
Dawn’s early light filtering through the curtains revealed my surroundings as I woke from deep sleep. Sylvia’s bedroom. Sylvia’s bed.
Not new information, but it hadn’t really hit me until that moment. The room had been dark. I had been busy—fucking. Much of the time my head had been buried between a luscious pair of thighs.
Now I could just begin to see the environment around me. By all rights, I should still be sound asleep, as my lovely bedmate was. Four separate rounds of lovemaking—unless I lost count—left little time for actual sleep. What had woken me I couldn’t say, but now I lay there wide-eyed and awe-struck.
In many ways it was an ordinary teenage girl’s bedroom: mementos and souvenirs, various trophies, ribbons, award certificates in frames on the wall. A brainy girl, too; books everywhere. To my right, I could just make out the larger titles standing in a bookshelf: Far from the Madding Crowd, Northanger Abby, To Have and Have Not.
That’s one fits, I said to myself. I have fucked Sylvia Beth Raleigh, and I have not fucked her.
But I felt the sweetness of success at any rate:, even if only in make-believe, finally fucking her. All night long we’d rolled in the sheets, my slippery dick sliding in and out of her pussy. Twice I had unloaded deep inside it, once up her ass, and one time between her massive breasts. Then I’d lapped up every drop with my tongue and we’d shared it together in a ravenous cumkiss.
The illusion had done its work, a potent memory stamped onto my subconscious. At no time had I completely forgotten I was screwing not Sylvia herself, but her mother Anne. But it felt like reality, and where there had been insecurity, anxiety, and intimidation before, now I was aware of calm confidence and determination. Whenever I finally nailed Sylvia—and I felt certain I would—I now stood a decent chance of performing adequately. With enough practice between now and then, maybe I could even impress her.
That made me ponder all the action that bed had seen. Minimum three dates a weekend is twelve guys in a month—not all that many, really, considering how many cocks were gunning for her. Since her defloration, seven months earlier and change, that made eighty-four penises, not counting threesomes and group sex.
So who was this guy she was dating exclusively now—and why him? Mostly it was curiosity driving me, but also logic: figure out what he had that all the others didn’t, and I’d have key insight on how to get a jump on the competition.
The room was now light enough to see everything clearly. I looked around for clues to the guy’s identity. If I could only get out of bed and rummage around, but I didn’t want to wake Anne—as horny as I was to do her number five. Hard as she had worked, she had earned her rest.
Then I saw something: a frame standing on her bedside table, maybe her boyfriend. I turned it, but it wasn’t him. It was just a shot of Sylvia and her inseparable best friend Jill striking a silly pose at a beach somewhere. I admired the bikinis, for sure, especially how skimpy they both were.
Jill was smoking hot, for sure: redheaded, freckled, that tomboy vibe. Jill would have been the best-looking girl in any room, were she not constantly eclipsed by Sylvia’s magnificence. Which she didn’t seem to mind, content to be a kind of sidekick to her best friend.
I had enjoyed her with my hand on many occasions, though their friendship made it unthinkable I could ever date Jill myself.
I had been on one date with her, however—a double date: me with Sylvia, my pal Gary with Jill. Best friends with best friends. It seemed like a slam dunk at the time, but afterward, Gary and I memorialized it as “the date which will live in infamy.”
Ir was a couple of years earlier. So, we were all just kids. We figured we take the girls to an amusement park, and it would be thrills all day, two-by-two. The girls would do a little screaming and need some hand-holding, the comfort of a strong masculine arm. A natural lead-in to kisses after sundown.
Ir seems the girls were less into that kind of deep romance and more into having some yucks at our expense. So, from the get-go, they made it two-by-two all right—only girls in the first car, leaving us two boys to ride behind them in the next. Talk about humiliation. Talk about dashed hopes.
Eventually, the two practical jokers had pity on us and started pairing up the conventional way. There was no hand-holding, however, much less smooching. It was not one for the record books.
That one had always cut like a knife, since that time, but even that pubescent ball-busting trauma felt more like a silly anecdote now that sexually mature Sylvia and I had done the dirty in her bed—vicariously at least.
Something else was on her bedside table: a seriously well-read book, the cover missing, the binding cracked, pages dog-eared. I picked it up and turned it toward the dim light. The title page said Emmanuelle.
Oh my god, this was Sylvia’s book of books! I looked inside, and it was filled with underlines, annotations, little stars, and exclamation points. What was it doing here, I wondered, if she read from it every day? She must have another copy, a newer one, with her where she was staying at Beverly’s.
But this was a goldmine for me. I leafed through the first pages to see in particular what she had underlined. The opening chapter was called “The Flying Unicorn.” Next to it was a drawing in blue ink of a horse with wings and a single horn on its forehead. Only, on closer inspection the horn was a penis. It was ejaculating, spouting a stream of droplets. The droplets turned into little hearts. Cute.
I found a section of heavy underlining. I read from the beginning of the chapter for context. Imagine, being in Sylvia Raleigh’s bed on a sex-romp weekend, and reading a book in bed instead of fucking. Actually, in Sylvia’s world, that didn’t seem so outlandish.
As I read, my fantasy-factory of a mind created a Technicolor version starring Sylvia and a cast of familiar faces. Sylvia is Emmanuelle, who is boarding a plane to fly across the world and join her husband—me, naturally.
She flirts with a pretty blonde stewardess, portrayed in my mind by Jeri Lear, my new stewardess-escort friend. Emmanuelle begins to caress herself, thinking about the girl’s breasts, perhaps. I had never seen Sylvia masturbate of course, but in my fantasy, she looked delicious in the throes of self-induced pleasure.
While it begins as a do-it-yourself job, Emmanuelle does not finish alone. When you’re a woman like that, you can always rely on the kindness of strangers. So, the anonymous gentleman seated next to her—who oddly looked a bit like Dr. Raleigh—is more than happy to lend a helping hand.
Older and wiser—and with no thought other than her well-being—he provides her mature guidance. In a section double-underlined in red:
“He leaned toward her, extending his other hand, took one of hers and drew it inside his trousers. He helped her to grasp his rigid penis and guided her movements, regulating their length and cadence to suit his taste, slowing them or accelerating them according to his degree of excitement, until he was convinced that he could rely on her intuition and goodwill and let her continue the manipulation in her own way.”
The kind gentleman’s cock, is played, in a cameo appearance, by none other than yours truly. Next, in triple-underline, our young heroine rises to the occasion, justifying the trust placed in her capable hands:
“When his satisfied penis finally disgorged its semen in long, white, odorous spurts, she received it with strange exaltation along her arms, on her bare belly, in her throat, face, and mouth, and in her hair. It seemed that it would never stop.”
In the left margin, she had noted, in red, all caps, circled and starred: “SATISFIED PENIS!”
Mine was, at the moment, enjoying the urge to be satisfied. As much as I was looking forward to more fucking, I wasn’t about to wake the nude woman sleeping beside me.
The book made for ideal one-handed reading though, and I had Kleenex next to me on the side table. I just needed something like moisturizing cream to do myself properly. I figured odds were I’d find something suitable in the drawer.
In this I was not disappointed. Clearly, I was on the boy side of Sylvia’s bed, as the drawer was filled with a collection of condoms, cock rings, anal vibrators, and several tubes of lubrication. I was sure guys didn’t often need to masturbate in bed with Sylvia—unless requested to perform for her. God, I’d have loved to do that for her—demonstrate my love with passionate worship!
My plans quickly changed when I heard my “Sylvia” stirring next to me. She turned and kissed me, and she checked my status—which was rock-hard and ready to rumble. She had a better use for my erection than I had been contemplating.
“I’m sopping wet,” she said, “I’ve been dreaming about you. I need you up inside me—now!”
So much for foreplay. We had typically engaged in long bouts of oral before plunging into one of the lower orifices, but the lady must be obeyed. In a flash, I was atop her and my dick deep into her hot, soft, moist pussy.
It was a beautiful fuck: nothing stylish or graceful, just a full-on drive to slam, top speed, into orgasmic ecstasy. She was whimpering and moaning. Me, I was calling out her name, nothing new. Only it broke the role-play protocol: “Mrs. Raleigh! Mrs. Raleigh! I love you! I love you!”
She came first, shouting a stream of dirty words. I kept on pumping, hoping to give her a second wave before I exploded. I did, and she did, a split second before I burst and stuffed her cunt full of jism.
“Eat it!” she ordered, as she had every other time. So, I went down and sucked out the goodness. I swallowed most of it—for nutrition’s sake—but kept enough to share with her.
As we collapsed together on the pillows, she began laughing. “Don’t you think that’s a little weird, screaming my mother’s name during sex?”
“Hmm, you’ve got me there,” I replied. “Sylvia, darling, I love you with all my heart. You’re the woman of my dreams. But I have a confession to make. What would you say if I told you I’m also secretly in love with your mother?”
“You are?”
“I totally am. I’ve got a hard-on for your mom the size of Milwaukee.”
“Is that right?”
“Afraid so. I hope that isn’t a problem…”
“Oh, you’re not the first one. Not by a long shot. Mom and I share all the time. With you… I admit it’s slightly unexpected, but no, definitely not a problem.”
“Good to hear… wait! Is that bacon I smell?”
“The advantage of being a Saturday night date is Sunday morning brunch. Usually, it’s my mom who cooks it, but for some reason, my dad is doing it today.”
“That works for me.”
“I tell you what, Martin. Under the circumstances, this little revelation of yours, why don’t we end the role-play for now? That way we can spend the rest of our time seeing what we can develop between you and me?”
“Meaning you’re Mrs. Raleigh again?”
“That’s right, Only, maybe it’s time you started calling me Anne.”
“I love you, Anne,” I said, and we kissed.
“Listen,” she said. “Sylvia’s bathroom is the first door on the left. “Get yourself a shower. Boy towels are the blue and white ones in the cabinet. Help yourself to one of the new toothbrushes in the drawer next to the sink. I’ll go freshen up in mine and meet you at the breakfast table.”
I showered, dried off, and emerged naked. We had not set specific nudity rules for the Raleigh house, but I understood my duty was to stay unclothed as often as humanly possible.
Still, I was self-conscious about it—a feeling I enjoyed—not knowing who was and wasn’t home.
Dr. Raleigh shook my hand when I arrived in the dining room.
“I love it,” he said. “Exhibitionism totally suits you.”
He evidently saw me looking around and understood. “Estelle will be sorry she missed seeing you.”
I let out a sigh of relief, though part of me was sorry she missed seeing me, too.”
“She always gets on well with Sylvia’s guys,” he told me. “Keeps track of all their names better than Sylvia does. We thought in this case—the whole role-play scenario and all—it might be best she spent the weekend at a friend’s house .”
“She’s really growing up fast.”
“Not fast enough, as far as most of the guys are concerned.”
At this point, Anne joined us, wearing a royal blue satin robe, barefoot and, I guessed, naked underneath.
“I’m me, honey,” she said, as she kissed her husband. “Martin and I plan to get to know each other a little better today.”
“Wonderful. I knew you were in love with Sylvia, Martin. But I always thought you’d make a good boy-toy for Anne when you were old enough.”
“Boy-toy?” I said with a laugh.
“That’s what Duke likes to call them. I do like to keep a few young men around for fun. Though you’d be my youngest; that’s for sure.”
“Sylvia told me you two shared her boyfriends sometimes… actually, that was you…”
“Confusing, isn’t it. Yes, some of her boyfriends become my ‘boy-toys’ and vice versa.”
“That brings up something I’d like to ask you. About Sylvia.”
“Yes, what’s that?”
“You told me that recently she started dating one man regularly…”
They both gave me a puzzled look.
“I said that?” asked Anne. “I don’t believe so, Martin. Because that isn’t the case. Not at all.”
“Did I dream it?” I said. “I distinctly remember…”
“No, my love, you have misunderstood something. I admit I didn’t go into one—minor—detail.”
“Minor detail?” repeated Dr. Raleigh with a chuckle.
“Yes… Actually, Martin, what I said was she has started dating someone regularly. I never said it was a male.”
“You mean… a female?”
“You knew she was bisexual.”
“Yes, of course, but…”
“And you knew Beverly was training her…”
“God, yes. Just the thought of the two of them having sex together… And I imagined with other women, too. That’s only natural, from what Felicity tells me.”
“That’s right. Women are naturally bisexual, though many are unclear on the subject, sadly.”
“So, it makes sense that Sylvia sometimes fucks girls, but dating a girl? And exclusively? I have to admit I didn’t see that one coming. I take it you mean she and Beverly are dating.
“No, Beverly is her amica, but her girlfriend is someone else. I’m sure you know Jill.”
My jaw dropped. “Jill? Jill Cannady? Her best friend?”
“That’s right.”
“I mean, I saw the picture of them together on Sylvia’s bedside table.”
“That’s from their first date. This is how it all happened: Beverly seduced Sylvia, her first lesbian sex, not unexpected. In fact, we had discussed with Beverly the possibility of serving as Sylvia’s amica one day. It all made perfect sense, but we all agreed it should happen naturally, flow out of their student-teacher relationship, as often happens.”
“Sure,” I agreed, thinking about my French teacher, Mrs. Cody, wishing something like that could happen between her and me.
“Beverly trained her to eat pussy, but also to suck cock and, after her deflowering, to fuck. Sylvia went to town with the guys, as you know. But Beverly suggested it would be fun to seduce girls, which she did, with amazing success. So, Beverly thought, why not seduce her best friend?”
“Looks like that worked,” I said.
“It wasn’t difficult. You see, Jill has always been in love with Sylvia,” said Anne.
“Which was always perfectly obvious,” added the doctor.
“Hmm. That does make sense of a few things,” said I, thinking of that double date debacle.
“I don’t know about Jill,” said Dr. Raleigh, “but for Sylvia, she’s just experimenting. She most definitely loves cock—way too much to give it up for long! But twat is fun, too. I’m sure you’d agree, Martin.”
I looked at him and smiled. “Your wife’s twat sure is.”
“That’s for damn sure. And I’m looking forward to watching you enjoy it today if that’s all right.”
I looked at Anne and looked back at him. “It’s sure okay with me if that’s what you’re asking.”
“I look forward to being cuckolded, then, in a little while. But speaking of dating, what about you?”
“Yes, Martin,” said Anne. “Are you seeing anyone special these days?”
That struck me as a very odd question.
“Well, I mean… my mother, then Felicity, Zoe… and of course now, you… just to name a few.”
“Yes, dear. When it comes to recreational sex, and your ongoing erotic education, of course, you have lots of us to play with. And I don’t need to remind you how important it is for you to practice having sex with as many different women as you possibly can.”
“No, go ahead. Remind me.”
“That’s different, though, isn’t it, from your personal dating life?”
“You mean on top of all this…?”
“Of course, dear. And at your age, it should be as many girls as you can. There must be someone you’ve had your eye on. In addition to Sylvia, I mean.”
“Well, I went out with this girl named Betty a few times this past year.”
“You and Betty never fucked, obviously. Since you were a virgin until the other night. But some oral, I’d imagine.”
“No, I’m afraid not. I mean we only made out, and I fondled her breasts a little.”
“Well, that’s a nice start. What about picking things up with Betty? You two have some unfinished business, it seems to me. Anyone else?”
“A hot blonde in my class named Heidi. I always wanted to ask her out, but never got the nerve.”
“Call her tonight and ask her out for next weekend. Take her out and then fuck her. Nothing easier.”
“Okay!” I said. “And someone else I’m really interested in is Jeri Lear.”
“Oh, John and Joann’s daughter….
