Young Greg Ch. 04: Claiming Manhood

When I arrived at Roger's house a few days later, I told him right away that I had been to see Loretta. "I know," he said. "She told me all about it. So you're going to spend time with her? That's good. She's a sweet lady and you will learn wonderful things from her."

"I was afraid you might be unhappy," I admitted. "I mean, you and me . . . , you and her . . ."

"No worries, my boy," Roger assured me. "You and me are about man sex. I will never get between you and any woman. As for Loretta and me, our relationship goes back decades, and is not exclusive, by any means. We've been with each other, on and off, through my marriage, several of her older boyfriends, and many of my young boys just like you. She's been with some of them, too. Just enjoy her, be good to her, and learn from her." As I visibly relaxed, Roger held me and gave me a big kiss and squeezed my groin, and we started undressing.

When I was exposed, Roger took my cock in his hand, stroked it, then knelt before me and slid it into his mouth. The sucking went on for a long time, and his finger was in my asshole. I held his head and fucked his face as he reached up and pinched my nipple. After a few minutes more of this, I tensed up, moaned loudly and blew my load down Roger's throat. When I finished, he stood up and gave me a deep French kiss, sharing my come from his mouth to mine, and we both swallowed. I reached down and squeezed his huge penis, rubbing it against my crotch. I sat him down and began sucking his dick in return for the amazing blowjob he had just performed. After a bit, I turned him over and started rimming his anus with my tongue, making it as wet as I could get it. Roger made noises as I continued licking his ass, reaching around with my hand to hold his erection.

Licking and masturbating Roger simultaneously was making him very hot, and my boner had returned, so I mounted him and pushed my little penis into his slippery-wet asshole. I humped him slowly and deliberately, as I continued to squeeze and rub his big wang with my hand. He became more feminine than I had ever seen, pushing his ass back against me and making woman noises, whimpering, "Fuck me, Greg! Take me! Make my ass yours!" I let go of his penis, put my hands on his shoulders and did my best to climb on his back as I penetrated his rectum, again and again. Roger moaned and sobbed as I repeatedly plunged my full length into his butthole. I was possessed, claiming him for my own, becoming the alpha man after weeks of being the protégé. Eventually, I felt my nuts start to tighten, and the come began to rise from the base of my shaft. I pounded his ass harder with every stroke, until finally I yelled at the top of my lungs and released stream after stream of hot come deep in Roger's hairy fanny. At the same time, he groaned, "I'm coming!" and ejaculated huge globs of semen onto the bed below.

After Roger calmed down, I withdrew my dick from his now-gaping sphincter, reached under, and tenderly squeezed his big balls. "Your ass is mine, now, baby, and my ass is yours," I said.

"Yes, you're the man today, Greg," he assured me, as I lay down next to him to relax, idly running my fingers through his pubic hair and caressing his sticky cock. "That being the case," he continued, "there's something you need to do. You need to grow your crotch hair back in. You need a hairy bush, both for me and for Loretta, too, just to show that you're not a sissy, hairless little boy, but a man, with a man's dick hair between your legs." He gently fingered my smooth pubis, and I resolved that I would shave no longer down there.

In the early days, as my bush started to grow back, both Roger and Loretta lavished extra oral attention on my cock and balls, taking pleasure in the stubble with their mouths and tongues. As it grew in and softened, Roger took great enjoyment in frotting me with his large penis, and Loretta fucked me tenderly, always managing to rub her pubic hair firmly against mine.

After a couple of months, my big bush was mostly back, and both of them complimented me on it, generously and often. In particular, Roger loved to press his dark brown bush against my blond one, and see the hairs all mixed together, while Loretta, who loves watching men masturbate, had me play with myself in front of her repeatedly, so she could watch my penis grow from limp and small to fully erect, in the middle of all that blond hair. She would then lean forward to take my dick into her mouth while rubbing her nose in my crotch fur. Sometimes she would suck me off and swallow every drop, while other times she would sit back and enjoy the show as I whacked myself to a gushing orgasm. Afterward, I always got to slide my second boner deep into Loretta's pussy or asshole. I think it was because of my small penis that I got to assfuck her frequently.

One day, I called Loretta on the phone. "Just letting you know, I have a date tonight. With a girl," I added, just so there was no mistake.

"Wonderful!" she gushed. "I'm so happy! You've learned all you need to know. You can make this girl happy in bed.

"Don't push her too fast, though," she cautioned. "The first date is too soon. Somewhere around the third or fourth date, if you're both still aroused, is a good time to try. If it takes longer than that, she'll think you're not interested. Either that, or she's just not that sexual. Nothing wrong with that if it works for you, but I know you, my boy, and I don't think it does. Not after what you did to my pussy last Wednesday night.

"If you like, stop by my house after you take her home. I'll wait up and we can talk, or whatever." "Whatever" sounded good to me, and I told her I would.

That evening, I picked up Evie and we went out for drinks and to listen to a local band. We had a wonderful time. We talked, drank, danced a little. With her body pressed against me, I started to feel that maybe, at last, I could have a normal sexual relationship, besides all the older man and much older woman stuff that was going on with Roger and Loretta. I gave Evie a couple of little kisses on the dance floor, but heeding Loretta's advice, didn't push too hard for more intimacy. Afterward, we stopped at an all night diner for a late bite - breakfast at midnight - and I took Evie home. At the door, I kissed her again, and she made it last for a long time, with just a hint of tongue. I told her I hoped I could see her again, and we said goodnight. I got in my car and headed to Loretta's. I was aroused, and I knew she'd at least want to watch me play with myself. After that, who knows what might happen?

When I got there, although it was late, I could see Loretta's lights were on, so I rang the bell. She welcomed me in, all smiles, and had a pot of coffee ready. We sat and I recounted the date to her. I told her about the dancing and the kisses. How I had gotten aroused, and how I thought that Evie had, too. She told me I had done the right thing, and hadn't pushed the girl too hard. "I know you want to get in her pants, Gregory, but give her a little time. Let her play it out in her mind for a while before you take her there." Then she unbuckled my belt, and said, "So let's see if your dick is still stiff. Is this girl that good?"

I pulled my slacks and briefs down, revealing to Loretta that my penis was, indeed, still erect. She fingered my hairy bush, then grabbed my pole and led me to the bedroom. The bed was already turned down, the pillows piled up against the headboard. Loretta stripped as I took off my remaining clothes. I held and kissed her tiny breasts, and suckled on the big nipples, ran my fingers through her gray pubic hair, and took my position on the bed. When Loretta was seated in place between my spread legs, I squirted lube on my cock and began stroking. She leaned forward, to take my dick and balls in her hand, but I stopped her. "Just watch," I told her. "This one's for you." She began diddling her big clit, and I went to work.

Time after time, I stroked my rod up to the point of coming, then stopped and waited for it to shrink again, to a little, limp sausage. Each time, Loretta thought I was going to finish, and each time I stopped short, building up the suspense. While this went on, Loretta frigged herself to three or four orgasms, the outside of her pussy plainly wet and glistening. By the end, she was begging me to come for her. Finally, after six or seven cycles, I was ready once again to shoot off. I acted as if I was going to stop one more time, but at the last minute, I pounded my boner fiercely, and launched huge loads of come in the air, landing on Loretta's face and tits.

When I was finished, Loretta scooped up the come on her face and body in her hand, gave me a grin, and then ate it. She pushed me over on the bed, away from the headboard, and straddled her skinny legs and ass over my face, demanding, "Eat me!"

I reached up with my tongue, as far as I could, and licked. I got wet pussy, pubic hair, and that enormous clit in my mouth. Licking up and down Loretta's erect clitty shaft, I heard her breathing hard. I could feel my dick getting stiff again, but was unable to reach it with my hands. So, I humped the air behind her as I licked furiously on her stiff bean and her hairy pussy lips. I reached up and held her titties in my hands, and when she gave the first moan of her orgasm, I pinched both her nipples, hard, and made her scream just as her pussy let go and flooded my face with her rush of wetness. I kept up the fast licking until Loretta shouted, "Stop!". I did, and she flew off my face, spun around, and landed her wet cunt on my erect cock in a reverse cowgirl. Wasting no time, she bounced up and down on my penis, and by the time she made me come again, she had orgasmed one more time as well.

I was wasted, as Loretta climbed down off me, slid a pillow under my head, pulled up the covers and nestled herself up against me. "Sleep, Gregory, my pretty boy," she whispered. "Sleep all night long. You can go home in the morning."

In the morning, I awoke as the sun came streaming in the window. I was lying on my back, on top of the covers, and I had a full erection. Loretta's hand was resting on my pubic bush, and as I stirred, she woke up and gripped my penis, stroking its full length slowly but firmly. "Good morning, big boy," she whispered. I turned my head and gave her a kiss. I thought she was just idly playing with my dick, but she continued masturbating me, so I grabbed the bottle of lube and squirted it liberally over my crotch. Her hand working my wet cock made a slapping sound, and it wasn't long before I launched a geyser of white come, hitting my shoulder and face and the nightstand. I pushed Loretta back on her back and began fingering her hairy pussy in return. She was already wet, and her huge clit fully erect. Took her about four minutes and she was howling like a wolf at the moon as she orgasmed hard under my hand.

We got up and I had a cup of coffee while she made some breakfast, both of us wearing only underwear from the night before. I ate my scrambled eggs and sausage before standing up, giving Loretta a deep, long kiss and squeezing her tiny titty. Then, I pulled on my clothes to head home for a shower.

At home, I was in the middle of sending Evie a text message, thanking her for a fun evening, when my phone rang. The screen displayed a number I didn't recognize, and I answered. "Hello?"

"Hi, Greg?" a voice asked. It sounded vaguely familiar. 'This is Steve."