Sappho and Catullus Ch. 08

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Pamela preps Matthew. A strip-planning session for the girls.
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Part 8 of the 10 part series

Updated 06/11/2023
Created 11/25/2021
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PREPARING PARADISE

Matthew is launched on his sexual journey. Catherine and Michelle get more and more excited as they plan the big day when Michelle will introduce Catherine to Matthew.

Michelle my good angel

The way you describe your night with Catherine, it's as if you were present at a new birth. She found herself years ago, after meeting Eudora and Philippa, but you sealed it for her. Now that you have shared so intimately with her, neither of you will ever be the same again. It means that when I meet her, I will be able to breathe in the special connection you have. I don't feel jealous. This is not a competition. Nor is it purely a sexual experiment. It's an adventure, something we're embarking on together. Who knows where it will lead? But I trust you and I trust my love for you.

Pamela came to see me in my little apartment a few days after we had reached the top of the mountain with Marie and Susannah. She hadn't visited often, although she always enjoyed the change of scene and the way she was bringing her womanhood into my bachelor's pad.

"Matthew, we're going up a level."

There were more? I thought we had gone as high as it was possible to climb. A little learning might be a dangerous thing, but I'd already learnt a lot. Well, I was game.

"I've taught you how to please a woman, and you've shown me and Marie and Susannah how well you can do it. You're patient, tender, passionate, considerate, appreciative, fun to be around, all those things. But we are older women, women of experience -- mostly bad, I know, with men, but we know what we want and we are comfortable with ourselves and with our bodies. That's not always true of younger women. They fuck us up, our mums and dads, you know? So we have to get unfucked up so that we can fuck and be fucked."

"Do you think I'm unfucked up yet?"

"Pretty well. You're getting there. But now you have to get your own girl. We can't just supply you."

I wasn't sure I liked this. I was quite happy with the supply. It was meeting my demand, and then some.

" You want me to go independent?" This was scary.

"Semi-independent. You can still fuck me whenever you like, and Marie and Susannah would love you to visit. That will make up for any disappointment."

"Who am I going to disappoint?"

"You won't disappoint anyone, not if you keep it up as you have been . . . keeping it up. OK, that was lame (but not limp). She might disappoint you, your new girlfriend. And then you'll need some make-up sex with the women you know can satisfy you."

"As long as they are not making it up or faking it."

"Trust me. Trust us. When we come, we come." She closed her eyes for a moment, breathed deeply, and went on: "And this is how it's going to work. Have you got anyone in mind yet?"

I hadn't even been looking at anyone since Pamela had taken me in hand. "No, not really. But there's this new girl at work, Cynthia. She's cute; not just cute, when I think of it -- she's got what it takes. Not nearly as good as you, of course . . ."

"You don't need to flatter me. Just feel me up. That's right. Ooh, I like that." I was tracing the outline of her breast. "OK, so first you must ask her out. Take her to dinner. Will you need any money, if you take her somewhere special?"

"No, this will be worth every penny."

"Pennies won't get you very far, but OK, that's settled, then. You let me know when it's going to happen, and in the afternoon I'll come up to your apartment. We're going to have long, breathtaking sex."

"Why? Not that I'm complaining. I'd love it. But shouldn't I keep my appetite?"

"Yes, keep your appetite for the food. Sex will increase your appetite for that. The point is, it will also make you think like a woman. While you're wining and dining her, you can't be thinking about how you're going to get into her pants. The first date is the one where she needs to be reassured that you like her for herself. There's going to have to be another date, the one after you sleep with her for the first time, when you're going to have to reassure her again, in case she fears that's all you want."

"How do you know all this?"

"I know what I would like. The girls today are much bolder than in my days. She might just jump your bones anyway. But things can't have changed all that much. When she first opens her legs for you, you're going to have to make her come. Her first orgasm with you is the key. She won't be a virgin, you can assume. If she is, then we move to Plan B. But let's just assume she isn't. So she'll have had some experience. You're going to have to make sure she wants to come back for more from you."

"The pressure!"

"High-achievers perform best under pressure, you know that. And you don't have to feel nervous. Your cock won't let you down. That won't be the problem. It's learning to love that counts, keeping your mind on her and her needs while you're fucking. But don't expect to go all the way on the first date. Don't even think about feeling her up. No, I don't mean now, Matthew. You just keep feeling me up. Get your hand down there, yes, that's right" -- guiding me firmly.

"Why are you doing this all for me, Pamela? How do I deserve this? All I did was stare up your blouse and you're taking me to your bosom." Fitting my action to the word, I nuzzled up to her tits.

"That's why. And if you keep doing that, I'll keep doing this." Her hand went to my manhood. But the conversation continued.

"After the first date, you come to me, and you fuck me, hard, while you're thinking about her. Then you can let it all out. You can talk to me about her eyes and her lips and her tits, all those things you want to enjoy. And you can pump away at me as much as you like while you're about it. I can take it. Fantasize about her and thrust into me. I'll love it. It'll keep you hard and I'll come again and again. After that, we'll do some more planning."

Wow. Every young man should have his Pamela. We need grooming, you know. I'll tell you more about Cynthia next time. I want to find out what you've got planned.

Your always-adoring, always-erect-for-you

Matthew

My well-groomed lover

That was good advice Pamela gave you. I think it's one of the reasons why, when I met you, I knew. Not only were we were going to have great sex -- and I've never known anything like it -- but we were going to be great simpliciter.

I say I've never known anything like it, and that's true. You can't compare it with fucking Catherine -- that's just different. Vive la differance! Put the two together, you and Catherine, and the chemistry will blaze. I'm not talking about your stereotypical threesome: I lick you, she licks you, we lick each other, you fuck her, you fuck me, we get some breast treatment in between. That's like turning Shakespeare into Run Rabbit Run. Actually, Catherine knows all about Shakespeare, thanks to Eudora and her colleagues. Let's see how that works for us!

Seriously, though, we're going to get this right and we're going to go into orbit.

So Catherine and I got out the G & Ts again, in honour of our first time, and had a planning session. We thought it would be fun to turn it into a game, in case we took it too seriously. It's got to be playful, my love, or we're just going to start laughing in the middle of it and you know what that can do to your not so ancient and far from honourable member. Every time one of us thought of a really good idea, the other one would take off an article of clothing. For encouragement, you understand. People say that cleavage makes the heart beat and the brain close down but I can tell you it makes me accelerate.

So here's the playlist.

First, I arrive at your apartment. We embrace, you and I, kiss and make out, keeping our clothes on and our climaxes at the ready. A gentleman knows how to delay his orgasm, doesn't he?

Catherine's top comes off. Nice. A peck on her pecs, and on we go.

Second, she knocks on the door. I let her in and lead her into the sitting room. You make the tea while she and I make out on the couch. Same rules.

My slacks go. Catherine's hand gives me a caress where it counts.

Third, I pour the tea and you go and sit next to Catherine. She touches you -- not there, no: shoulders, neck, hands, maybe your thighs. You're just getting acquainted with her touch.

Bra or skirt off next? Skirt. She's resplendent in her bra and panties. I just gasp as I did the first time I saw her.

Fourth, she kisses you tenderly and long, on your mouth. Getting to know you better. Meanwhile, I'm so excited to watch you kissing that I have to hold on tight to the armrest to stop me doing something premature. The kiss ends, she draws back and sends us off to the bedroom.

I unbutton my shirt but leave it on. She likes that look of breasts out but not yet out, too.

Fifth, we make love just as we like it. No acrobatics, no showing off, just the two of us. Of course she's watching. But I love her so much, and you do too, having read so much about her and tasted her lips, that we feel as private as if we were entirely alone. Both of us climax.

Catherine peels off her bra. Her nipples are standing out invitingly. Would I be me if I didn't give them a little attention?

Sixth, she joins us on the bed and we cuddle. It won't be long before you're hard again, and then I'll watch as you slide Max into her for the first time.

Catherine helps me off with my shirt and my bra. It's nipple to nipple and I'll leave you to imagine the rest since it's coming soon to an apartment near you.

So that's the script. Will it be all right on the night? I guess we will improvise . . .

Next time: Matthew starts his relationship with Cynthia, drenched in sex with Pamela. Catherine writes to Michelle in excited anticipation.

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