Young Greg Ch. 02: Roger and the GILF

After our first meeting, I saw Roger got often, usually once or twice a week. We spent a lot of time exploring mutual masturbation, touching, oral and rubbing our bodies together. I loved feeling my cock moving against all parts of Roger's body: his crotch, face, asscrack, armpits. We would suck each other's cock and finger each other's asshole, but neither of us penetrated the other's ass with his penis. Usually, I slept over. I loved the feeling of being wrapped up in Roger's arms, from behind, with that massive organ pressed against my butt, and of laying my head on his furry chest, gliding my hand up and down from Roger's pubic hair to his nipples and back again. Sometimes, I would spoon Roger from behind, pressing my little dick against his ass and reaching around to hold his big penis in my hand.

Naked in Roger's bed, I enjoyed waking in the middle of the night and reaching for the sleeping man's cock. Sometimes, as I grasped it in my hand, it would be long and limp, sometimes already erect and massive. I thought more and more about taking it up my ass, wondering what it would be like having that big pole inside me.

Late one night, I awakened to the feeling of Roger playing with my ass. I spread my feet apart in the bed, to give him better access. He massaged my cheeks and spread them open, slipping a finger in between to tease my asshole. Enjoying that, I wiggled my butt in response, and felt Roger start to penetrate with a fingertip. We went back and forth like that for a while. I would wiggle, and Roger would push a tiny bit deeper. After a bit, he withdrew for a moment, then spread my ass with one hand. I felt something cold and wet and slippery on my anus, and then Roger's finger was back, pushing deeper than ever before, eventually burying his entire finger deep in my ass, then following it with a second finger.

I fucked my ass back and forth, then felt Roger pull his fingers out and climb between my legs from behind. He pressed his enormous dickhead against my wet asshole, and began to slide his big dong inside. At first, as his glans opened my rectum, it hurt a bit, and I whimpered, but he kept on, gently but firmly, and then he was all the way in me, my little penis jumping all at once to fully erect. I worked my butt up and down Roger's full length, while he probed it deeply within my ass. It didn't take long for him to let out a yell and start pumping feverishly as he unloaded his come in my hole. When the climax subsided, he gently pulled his dick out, wrapped his arms around me, his hand clasped around my still hard cock, and closed his eyes to sleep. As my asshole relaxed, I, too, fell asleep.

In the morning, I awakened first. I slid out of bed, walked around to Roger's side, found the bottle of lube and wet my cock down with it thoroughly. Quickly pulling off the covers, I climbed behind Roger and began rubbing my dick vigorously up and down his ass crack. As I became stiff, I found Roger's anus with my boner and, with very little effort, slid my little penis all the way in. Roger was just coming around as this was going on, and he grunted loudly but did not resist. I wrapped my arms around Roger's hairy body and fucked him wildly until I shot my come inside his asshole in one of the most powerful ejaculations I have ever experienced.

When the orgasm subsided, I did not withdraw, but clung to Roger's back, my penis still deep inside, until my erection shrank and it flopped out on its own. "So, my pretty boy," Roger murmured, "you really are a man after all." I squeezed him tightly and closed my eyes to rest.

One afternoon, we were standing naked in Roger's family room, facing each other and holding each other's penis in our hands. Unexpectedly, I heard the front door open. I tried to turn to grab my pants, but Roger held my erect cock tightly, not letting go. Just then, a well-dressed, older woman walked into the family room. She looked to be well into her seventies, handsome, tall and skinny, with collar length silver hair. I quivered at the surprise visitor, my erection disappearing instantly, as she announced, "Hi, I'm Loretta. "I'm the horny old lady from down the street, who comes by sometimes to get laid. Roger gave me a key and invited me to stop by today. You must be Greg. Let me look at you," she said, stepping up to us.

I turned toward her slowly, fully exposing myself to her. Roger had gotten me over any shyness. "Such a pretty boy," Loretta exclaimed, reaching for my balls. "Roger, of course, has that huge cock, but yours isn't too big, is it?," she said, stroking the back of my scrotum with her fingertip. "Maybe it's still growing. Go ahead, let's see you play with it." I'm sure I blushed as I took my penis in my hand, but didn't start rubbing it, feeling plainly embarrassed. "Oh, go ahead," Loretta instructed, as she began unbuttoning her blouse. "Nothing to be nervous about. All young boys like to play with themselves. Old guys do, too. Roger here loves to pull his pud," she said, nodding at him as he was, in fact, doing exactly that. "Have you ever watched him whacking off?" she asked. "I have. He can still shoot a great big load in the air."

I started masturbating slowly, my lost erection beginning to return in spite of myself, as Loretta continued to undress. I watched the old woman get fully naked, and I continued to tug slowly but purposefully on my hard dick. I took in her stick figure arms and legs, her wrinkles, her tiny, tiny teardrop breasts, drooping, but with fat nipples pointing forward, each areola nearly covering its entire breast, her skinny ass and her sparse gray pubic hair sprinkled below her flat belly, with lots of skin visible from underneath.

Loretta sat down on the leather sofa, spread her legs and gestured to me. "Come here, baby. Give Lorrie a blow job." A bit confused, I knelt down on the floor between Loretta's open legs, and realized what she meant as she exposed her enormous clit, hanging down a full inch below her mound, with a mushroom head, looking every bit like a little boy's penis. "That's right," she went on. Roger has a huge cock and I have a huge clitty." Amazed, just as I had been when Roger first stripped, I bent my head down into her lap. Teasing her clitoris with my tongue, it quickly stiffened and I sucked it into my mouth. "That's it, my boy," she cooed. "Suck my dick."

I sucked and ran my lips up and down Loretta's little shaft. She reached over to Roger and took his big, fat erection in her hand. "Such a big, wonderful tool, Roger," she told him. "You know I love it in me. If only the boy had a big one like this." She drew his body toward her as I continued eating her cunt, and when he got on his knees on the couch next to her, she turned and put her mouth over his dickhead, taking in as much as she could manage.

"Don't be mean," Roger cautioned her. "He stays hard all night, and you know you love a good prick up your ass."

"Mmmm, I suppose," she replied. "Anyway, he's quite a good cocksucker. Sit next to me, I want him to suck both of us off." Roger sat next to Loretta, putting his arm around her shoulder, and snuggled her as I shifted over and gazed at his enormous erection.

"Go ahead," Roger instructed. I took Roger's big dick into my mouth and slowly worked it back to my throat. I moved my lips up and down the shaft in long pulls, as Loretta took my hand and pressed it against her vagina. My thumb and forefinger found her swollen clitoris, and I began masturbating it with little strokes. After a bit, I switched back to sucking Loretta's pussy and gripping Roger's fat dick in my fist, and then alternating back and forth every so often.

Eventually, Loretta's breathing became louder, and I focused all of my attention on her, licking up and down her bean, and then swirling circles around it, ever more firmly and slowly. She began moaning perceptibly, and I reached up to squeeze her little breasts and pinch her swollen-stiff nipples. Suddenly, she tightened up, let out a yell, and soaked my face with a big rush of wetness as I began lapping furiously at her pussy. I kept licking as the orgasm subsided and Loretta began to relax, then turning my attention to Roger's big, stiff cock.

I popped Roger's glans into my mouth and began working it with my lips. As Roger made approving noises, I sucked harder, taking in more of his penis with each stroke, finally working the head and shaft in my mouth and throat in long sucking motions. After a time, Roger's moans grew loud, and he withdrew from my mouth, grasping his swollen dick in his fist, ejaculating in huge spurts all over my face, pumping it with his hand until there was no more come left.

Loretta was fingering her wet cunt, and said to me, "See? I told you his loads were huge." I wiped my face, swallowing as much of the sticky cream as I could capture. "All right, young man," she continued. "I think it's time for you to masturbate for us."

I lay back on the couch, my head in Roger's lap and with Loretta at my feet, and began stroking my hard little cock. I looked at her tiny tits and imagined sucking on them, first the left, then the right. I thought about her thin pussy hair and remembered it gently brushing my face as I had licked and sucked her wet cunt. The scent from her vagina had driven me wild while licking her. Roger caressed my forehead and pinched my nipples, while Loretta fondled my hairless nuts and my bare pubic area. My pounding became harder, and as I closed his eyes, Loretta climbed on top of me and lowered her vagina just over my cockhead, working it with her lips without taking it any deeper. Momentarily, I felt the come rising, and I thrust myself into her as I exploded with a great big load inside her cleft. As she relaxed and removed her pussy from my now-shrinking penis, she turned to look at Roger and asked, "Hasn't that big thing gotten hard again yet?"

Roger, once again playing with himself, his erection slowly returning, replied, "It's getting there."

"Then bring it over here and rub it on my slit," she continued, sliding back to lay on the sofa. "When it's stiff, you can fuck my pussy with it."

Roger moved between the woman's skinny legs, took his penis in hand and began rubbing it up and down her wet vagina, sticky with my come, making his boner grow bigger and stiffer. Finally, he slid it inside her with one long thrust and started fucking her with short, measured strokes deep in her pussy. Loretta started to squirm right away, as Roger's big fat dick stretched her cunt and pulled on her clit. He knew better than to pound away. His swollen cock was going to take a long time to come this time, and he wanted to control it as he worked it in Loretta's pussy, slowly but firmly grinding his hairy pubis against hers. She started to moan, and her moans became whimpers as Roger probed deep inside her. Shortly, she gave a yell and orgasmed hard, but Roger did not stop. As he kept up the pumping, adding more force now, she began to cry and she began to curse. "Oh, fuck! Oh, shit! Oh, fuck! Fuck me with that thing! Stick it in me! FUCK ME!" she yelled as she came once more.

I watched all of this, tugging on my revived hard-on, hearing the old lady orgasm, watching her clawing at Roger's back as he humped her from above. Moving behind him, I reached under and squeezed Roger's big balls as they slapped Loretta's ass. Catching some of her pussy wetness on my finger, I parted Roger's cheeks and quickly slid my finger up Roger's asshole. Roger groaned loudly and unloaded his come inside Loretta's vagina in several violent contractions.

As the pair started to calm down, I lay back on the sofa and masturbated vigorously. Roger and Loretta became aware of me jerking off just before I shot one more big load of come all over my chest and belly.

Loretta looked at me. "Young man, any time you want to play with yourself, feel free to stop by my house. You can come whenever you like." She smiled. "Just stop by and ring my bell. I'll let you look at my titties and my pussy, and I might even have a special treat for you now and then. You're good for an old woman."

I smiled back, swinging my limp dick in my hand. "I'll do that," I replied.