Sappho and Catullus Ch. 02

Matthew is really excited by Michelle's fantasy about the redhead she saw in the coffee shop. He enjoys telling her how he likes to jerk off, and then describes his own sexual initiation by an older woman at the age of twenty.

It's always good to remember good sex, new sex, safe sex. Go on Matthew's journey and learn what it is like to be made free.

Daring darling

I can't say what turned me on more: the way you described yourself or the object of your desire! In any case, you soon had my hand reaching down and things became pleasantly uncomfortable the further I read. In the end I went all the way, full of gratitude to you for giving it all to me.

Isn't it strange that there seems to be no shame about women pleasuring themselves, whereas with men, it's something you keep to yourself except in the locker room? We all do it, and we all know we all do it, but there's a pretence. And as for porn, there's a lot of hypocrisy about that, too. The whole thing is tangled up. We seek sexual release because we're turned on by someone, but then usually we need a bit of visual stimulation -- even words on the page, especially your words on the page -- to get to climax. Why? It isn't very logical. The truth is, most of us like sex; we like it a lot, and we're not just dealing with frustration or deprivation. We want all those things that we can get from the build-up and ejaculation: relaxation, excitement, living in our minds for a while, eventually losing ourselves in that moment of blessed release.

Even better when you can share it. Our lovemaking is exactly that. You called it coming home, coming home with you. So let's do it together. I want to make you as wet as you made me hard.

But until then, I must go solo. It starts with being alone. Knowing no-one can disturb me. And taking my time. First I boil the kettle, make a pot of tea and bring it upstairs with me. I get naked and put on my dressing gown. The first sip of my steaming cup is delicious, and then I gently steer my penis into position and pass my palm so lightly over it, balls to tip, that I am hardly touching myself. The hair stirs and lifts. A few deep breaths and I settle back, allow my shoulders to relax. It is time to slide my hand across my chest and down towards my navel. There is an immediate response; that pleasurable initial stiffening of anticipation.

You are in my mind, your v-neck, your eyes searching out her breasts, your panties dry but alive with growing desire. I indulge in a preliminary brush with my thickness and take a moment to savour the voluptuousness of it all.

And so to my favourite porn site. I like women alone; I like women going duo; I like tender hand-jobs and skilful blow-jobs. I used to like breasts best but now pussies delight me too, kissed and fingered and caressed. The whole of a woman's body excites me, and the way she gives herself to herself, to her lover, to me. Now the thing about porn is to give it a chance. It's no good surfing. You lose your composure and the leisure of the act if you frantically plunder the internet in search of some imaginary perfection, the scene you absolutely have to see. If the site is good, virtually any video can be a slow burn, and you can be sure of that if you navigate straight away to the right category. That usually means you have to pay honestly for your honest pleasure. Free wanking is second best.

I do have a bit of an underwear fetish, and I'm glad you're also an enthusiast. I don't want it to come off too quickly. I'd rather the camera dwelt lovingly on the shape and the fabric, the lace and the grip. So that's always a bonus.

But sometimes, especially at night when all is dark and my imagination can catch fire, I make up my own scenes. I relive those moments of real sexual awakening as a young man in my first job out of high school. I had just turned twenty, and I had hardly even fondled a girl's breasts, and that was just a fumble. Then one afternoon Mrs Tilletson, who had an apartment on the ground floor, asked me to help her hang the new wallpaper in her sitting room. She stood on the stepladder while I rolled the wet sheets up to her. When she positioned the paper on the wall, her top gapied away from her waist, giving me a perfect view of her ample breasts from below. I could even detect the pattern on her bra, which was white and lacy, soft and full. All afternoon I revelled in the sight, constantly renewed as we made our way along the four walls. She thanked me when we were done, but I should have been thanking her.

The next day she intercepted me at the bottom of the stairs, when I got back from work. She was wearing a light blue blouse and a darker skirt, very business-like. She meant business.

"Put down your things and then come back and see me," she instructed, and she didn't look pleased. Was I in trouble? As I took off my sports jacket and settled my satchel on the chair in my tiny top-floor apartment and pulled off my tie I felt that familiar tingle that, absurdly, used to go through me if I was about to be caned.

"Close the door and sit down," she said. I was in for it. "I want to talk to you seriously."

What was coming? The wallpaper seemed to be looking at me accusingly.

She went on: "When we were hanging the wallpaper yesterday afternoon, I think I caught you looking up my blouse."

Busted.

"Well, were you? Answer me." The tone was stern.

"I -- I couldn't help it."

"What do you mean, you couldn't help it? Do you mean you had no choice, or that you just had to look?"

"There was nowhere else to look."

"You should be ashamed of yourself. A young man like you, turning into a peeping Tom."

"I'm sorry; I shouldn't have. I didn't mean to."

"And so you should be sorry."

But did she have a right to punish me or tell me off? She couldn't report me to the police for sexual harrassment, just because I had stared up her blouse. I would soon be twenty-one. But the displeasure of a woman can be a frightening thing.

"It's degrading to be looked at in that way."

"I didn't mean to degrade you, Mrs Tilletson. You were lovely to look at." I stammered this out, not quite sure what I was meant to say.

"Oh, you thought so, did you? Well, I'll teach you 'lovely'. Go over and stand at the table, with your back to me." Why did I obey her instructions? Out of curiosity? "Good, now bend forward over the table."

I didn't see any cane or ruler or shoe. Maybe she had something handy. But she sat down in an easy chair. I bent forward hesitantly.

"No, that's not quite what I want," she said. "Drop your pants."

Was she really going to spank me? I hadn't signed up for this, but I loosened my belt and let my trousers slide down.

"Your shorts, too."

I pulled them down.

"Now, let's have a good look at you," she said, "just as you looked at me. See what it feels like."

Actually, it felt pretty good. My buttocks enjoyed the air, and her gaze turned the tingling into the beginning of an erection. A nervous erection, perhaps, but an erection all the same.

After a few minutes of silence, as she looked at me and I tried to concentrate on staying in control, she got up and walked over to me. Here it comes, I thought.

She put her hand on one of my bare cheeks, as if to prepare it for whipping. But it stayed there, just long enough for my penis to rise, the blood firming me up to the brim.

"Hmm," she said. "You'll do."

Was this a compliment? Was I a good target? Did she think she was going to make me sting?

And then an extraordinary thing happened. She let her hand pass over my cheek, between my legs, to cup my balls.

"Yes, everything seems to be in place. Is it in working order, I wonder?"

Goodness. She was going to find out pretty soon. I twinged. She leaned further forward and took me in her hand, from behind and below.

Was this some kind of ritual of humiliation?

"All right, young man, I know how to deal with this."

Castration? Torture?

"Turn around. Take off your shoes and socks. Put your trousers and shorts on the chair over there, and come and face me."

As soon as I was standing in front of her, my cock rigid against my shirt tails, she began to unbutton my shirt. She slid it off my shoulders, let it drop to the floor and took firm hold of my penis.

"Go through to the bedroom. Lie down on your back, and wait for me."

I made myself as comfortable as I could. There was no point trying to cover up my erection, so I just folded my arms on my chest, and waited. I didn't have to wait long.

"I'm glad to see you're not touching it," she said. "This might not feel like punishment. Actually it's not. It's education."

"What do you want me to learn?"

"I'll tell you as we go along. I want you to put your hands by your side and look at me."

I took in her matronly but well-proportioned figure.

"What do you see?"

"A nice lady," I ventured, hoping to placate her.

"No, I'm not a nice lady. Try again."

"An attractive woman."

"That's better. What do you find attractive?"

"You have a pretty face, but it looks a bit hard right now."

Her face softened, but she did not smile. "Go on."

In for a penny, in for a pound. "I like your figure."

"Yes; what about my figure?"

"Well, you have a nice slim waist." She did.

"Slim in proportion to what?"

"Well, you know, your upper body."

"You mean my breasts? Go on, say it."

"You have nice breasts."

"You would know, wouldn't you? You were staring at them all yesterday afternoon. But you don't really know what they look like. What's nice about them?"

"They are --"

"Don't say big. I'm not on a seaside postcard."

"I was going to say full."

"All right, that will do. Deep-breasted. Anything else?"

"Your bottom is shapely."

"Good. You can call it my ass. And call me by my name."

"Your ass is sexy, Pamela." I was beginning to get the idea.

"Better. Now take a better look." She drew herself up. "Well, what do you see?"

Her blouse flattered her bust. Her bra jutted against its crispness.

"You look very alluring."

"Thank you. Now you can touch yourself. Just for a few seconds. Good. Does it feel good? Would you like me to take off my blouse?"

This was like a dream. "Yes," I answered, but my throat was dry.

"I can't hear you. Speak up."

"Yes, please. Please do."

She stood quite still and slowly unbuttoned her shirt, from top to bottom, dislodging it from her skirt as she did so. At first I could just see the flesh of her neck, a little swelling above the cups of her bra and then her midriff. She ran her fingers down the edges of her blouse, momentarily brushing her bra.

"Open?" I nodded. She curled her blouse open, revealing her sharp nipple-points like little bullets. "And now, what do you think?"

"Every inch a woman," I said, beginning to feel a little more at home.

She cupped her underbreasts and drew a curvy line up, up, up, to the points. Then she crossed over and sat at the side of the bed. With one hand she pressed my hand to her bra. With the other she lightly felt my cock. Such bliss it was, to shape and weigh and fondle her warmth while she touched me. I yearned for her. My heart swelled up for her. We kissed.

I had never known anything like it. Her moist lips enveloped mine. I felt as if I was being drawn into a new, safe, happy, blissful world. No harm could ever happen to me. But more was to come. She reached behind her back to uncouple her bra. The straps slipped over her shoulders, the cups edged forward. Slowly her breasts came into view, first the broad base, then the swelling store, then the peaks. As her bra dropped away I gazed in amazement at the light brown aureoles and the pink nipples, prominent and firm at the centre.

"Suck," she invited me, bending forward. Her nipple sunk into my mouth and I drew a long, sweet taste. I swirled her with my tongue. My cock leapt and she took hold of it once more. A few skilful strokes and I could hardly bear it any more.

After I had suckled for a few enchanting minutes she positioned herself expertly above me, her breasts delectable a few inches from my face. Her skirt rode up her thighs and with a deft movement she pulled it up to her waist. I caught a glimpse of her panties as she slipped the waistband down, and almost before I knew it I was inside her.

If the kiss had made me feel safe, the moist grip of her cunt brought comfort I had never imagined. As she moved calmly, riding my penis, she imparted pleasure upon pleasure. "Move with me, dear," she instructed, and gradually I got to understand. I could sense her blood pulsing against me as my cock's head explored her innermost love tunnel. "Deeper," she cried, and I pushed further. Then I withdrew almost to the very entrance of her cunt, and without having to be taught, worked her lips. Thrust followed instinctive thrust. Warmth exchanged with warmth.

I looked into her eyes. She was biting her lip, her breath coming in gasps. She began to move faster. I held back, until she gripped my shoulders and began to shudder. Then I shot into her and she exploded. The pupils of her eyes contracted and she stifled a scream. This seemed risky. She covered her mouth girlishly, giggling. "I haven't come like that for a long long time," she said, and I felt good. "We'll have to do this again, and again, and again." I felt even better. "I'm going to teach you everything I know, and we're going to do stuff together. You'll see."

And now, just thinking of it brings me to climax. I hardly need to touch myself. Please come, too, come fast, come hard.

Come soon!

Matthew

Next time: Our two over-heated lovers exchange more letters. Michelle meets the redhead again. Matthew prepares to do his sex instructor proud.