Young Greg Ch. 03: Loretta's Story

Finding myself in the neighborhood - well, I had planned to be - I arrived at Loretta's house just after four in the afternoon. I pushed the button, and Loretta answered the door, giving me a huge smile. "You came!" she exclaimed.

I grinned and replied, "Yep. I wanted to come, so I thought I'd stop by and ring your bell."

She gave me a big hug and said, "Come in! Come in!" We walked into her living room, and she offered me a cold drink, which I accepted. "So," she began, "you're here to play with yourself for me?" I nodded. "Wonderful!" she exclaimed, giving me another big hug and a kiss this time, with lots of tongue. She led me into the bedroom, and together we turned down the comforter and the bedding. Loretta moved several pillows into a pile at the headboard, gave me a wink and said, "OK, let's get naked!"

We started undressing. I watched Loretta expose her skinny frame, and as I pulled my briefs down, I took my little cock in hand and gave it a few quick jerks for her to see. She had me sit up on the bed, with my back against the pillows and the headboard, and my legs parted in front of me. She sat facing me, between my legs, her legs stretched over top of mine, spreading her vulva for me to admire. "All right, Greg, it's time," she said. Let's see you start whacking off."

I held myself and, slowly at first, began running my hand up and down the length of my dick. As I watched her little boobies, her thin pubic hair, and that magnificent clitty starting to rise on its own, my erection appeared and I started stroking faster, a bit at a time. Loretta diddled herself as I watched, flicking her finger over her vagina, her big clitoris looking more and more like a little penis every moment. She reached over, moved my hand out of the way, and began masturbating me herself. My dick strained and swelled with every stroke of her hand. Finally, she stopped, said, "Finish it yourself," and leaned forward to begin licking my balls. Up and down the centerline, just as I would do licking a pussy. I resumed jacking myself off, and the feeling in my cock got more intense. I suddenly exploded a big load of come all over Loretta's face, followed by several more blasts, each smaller than the previous one. When I finished, she wiped her face and ate as much as she could scoop in her hand. Then she climbed on top of me, gave me a big kiss, sharing the come in her mouth with me, and rubbed her sticky face all over my face.

I eased Loretta back on the bed and put my face between her skinny thighs. My tongue found her long clitty and I proceeded to lick it vigorously. It pointed up, and I sucked it from root to head. I teased her sparse bush with my tongue and went back to sucking clit as she began to moan more loudly. When the climax hit her, she howled and shoved her vagina against my face, grabbing the back of my head to pull it tighter. Wrapping her legs around my neck, she rode out the orgasm and finally collapsed on the bed, breathless.

Moments later, she asked, "Is your thing hard again yet?" It was. "Then fuck me!" I rolled her over on her belly and she stuck her bony ass up in the air. Her pussy and ass holes were plainly visible from that position, so I got on my knees, took my penis in my hand, and slid it into her sloppy wet vagina. I could tell it was going to take some work to get me to my second orgasm, so I pumped Loretta's cunt for all I was worth. "It's going again," she yelled when the next orgasm started. I kept on pumping her hard, eventually pulling my cock out and lining it up against her butthole. Easing it in, I resumed the motion and Loretta resumed yelling. After a long time, I could feel it beginning. "I'm going to come," I said calmly, and I let loose with a load deep in her ass.

I lay down on the bed and closed my eyes. Loretta snuggled up against me, whispering over and over, "My boy. My pretty boy." After a time, I opened my eyes. Loretta was still lying on my chest, her hand resting on my crotch. "I'm so glad you came," she said. "I loved having you in my pussy and in my bottom. Such a sweet boy. Roger told me he loved how you woke up that morning and took his ass all on your own. No talking, you just did it. He loves you, you know."

"What?" I began. I didn't intend a love affair with Roger. Or with Loretta either, for that matter.

"You can love him, too. It's all right, you don't have to be in love with him. It's not like that. He loves all of his boys. Some of them still come to him to fuck sometimes, after many years. They all love him. You remind me of him, from years ago."

"I do?"

"Yes," she nodded. "Not in looks. He was this big, muscular guy, hairy from his head to his toes. And he had that python hanging between his legs, but he didn't really know how to use it properly. I guess it was about thirty years ago that I met him. He came to work at my company. He must have been about your age," Loretta said.

And you were about Linda Levy's age, I thought to myself.

"I invited him to lunch," she went on. "Then, the next week, to drinks after work. I brought him home that night and got him naked. I think he just expected me to go nuts when he took that thing out of his pants. I didn't, I've been around the block a few times, and I've seen my share of penises, big and small. But I oohed and ahhed appropriately, and I let him put it in me. He pounded away. It hurt. After he came and I didn't, I sat him down, poured him a drink, and we had a long talk.

"It turned out, no surprise to me, that he was very inexperienced sexually. He had dated girls, but hadn't gotten many of them into bed. The ones that he did make were shocked when they saw that huge dick. Some of them let him fuck them, some were too scared. In all of that, he never learned to be gentle, how to really make love to a woman, to bring her to real pleasure. He thought all he needed to do was stick it in and pump, and they'd all lose their minds. It was a real wake up when he figured out it doesn't work that way.

"I told him that I would work with him, teach him to be a lover. I told him it would take time, and we would come to know each other intimately. When we were done, he would know my body inside and out, and I would know his, and he'd be equipped to make love to any woman with confidence and without embarrassment.

"When he agreed, I had him come and stay with me for a while. I had him masturbating morning, evening and bedtime. After about a week, he totally jizzed out. I kept him at it, lubing his limp dick and making him have dry orgasms until he just couldn't do it any more. I mean, he wouldn't have popped a boner if he'd been interrogating Sharon Stone at the police station."

"Huh?" I asked.

"Never mind," Loretta went on. "It was an old movie with a famous beaver shot. After that, I'd sit him down, just like I did with you, both of us naked, and I'd tell him to get it up. He couldn't. I'd flip myself until this big clitty got erect, and I'd ask him what kind of man he was if even I could get a hard-on and he couldn't. He was humiliated.

"Then I started working on his ass with dildoes, small at first, then gradually larger. I told him if he was ever going to fuck women, and especially if he was going to fuck them in the ass, with that big log, he needed to know what it felt like. I made him eat my pussy until I came, again and again, and then I'd dildo him in the butt. If he ate me well, I'd be gentle. If he was clumsy, not so much. After a time, he learned to respect and appreciate a lady's vagina.

"I sent him home for a month. I told him I needed him to come back to me full of juice. No girls, no fooling around in the meantime. I locked a chastity cage onto his penis to keep him from playing with himself while he was gone. He could pee and wash with it on, but couldn't masturbate, and there was no room for him to get an erection. I wanted him good and horny.

"When he came back, I met him at the door, naked. I acted like nothing was unusual, brought him in, had him unpack his things, made drinks and then dinner, but naked the whole time. I didn't invite the poor guy to get undressed until late in the evening, after a long round of kissing on the sofa. I let him play with my little titties, but made him keep his hands away from my pussy while we were making out. Finally, when we stopped, he just looked at me like a little lost puppy dog. I let him take his clothes off and I let him out of chastity, and he grew the biggest, hardest erection I've ever seen. I took him to bed, and he made love to me in every part of my body. His cock was in my pussy, my mouth, my butt. It was on my nipples and in my underarms. I worried that, after waiting so long, he might get rough with me, but he didn't. He was gentle, and then forceful when appropriate, but not heavy handed. I must have come seven or eight times, and I think he came three times, and then again in the morning.

"I see you trying to be like that when you make love. You do it with me and you do it with Roger, and that's all wonderful. You don't need training like he did, you just need a little instruction and practice to get there. I can help you, if you like. This old broad has fucked a lot of men, some good and some poor, and I can show you the things that will make you a terrific lay. When you start making it regularly with girls your age, you'll get a lot of positive feedback. In the meantime, I think we both can enjoy the hell out of the process. What do you think?"

I nodded. This sounded good.

"I want to see you at least once a week, and I want you to see Roger at least once a week," Loretta went on. "Sometimes, we'll all be together. But I don't want you to fuck yourself out, so keep the masturbation to a bare minimum. I want you to always be able to get it up. If you have a date with a girl, let me know and we'll take that into account. But, no other boys on the side. Just use Roger when you want penis."

I pulled her close to me and gave her a big hug. Then I said, "I want to go take a shower now."

"I'm coming with you," she said, and we got up and walked to the shower stall.

When we got in, Loretta aimed the shower head at the wall and turned on the water to let it warm up. She then gave me a big hug and pressed herself against me, and I felt her hot pee running down my leg. It felt good and I smiled. When she finished, I reached down and arranged my penis in the middle of her pubic hair, and let my own pee stream go down her pussy and her thighs. It went on for a long time, and Loretta sighed with pleasure, "My pretty, pretty boy." She readjusted the shower head and we washed each other and dried ourselves off, dressed, and went to get a bite to eat.