“Ted? I want to show you something,” I said while undoing the knot in my robe. I looked at Ted’s expression when he looked down at my crotch. It was one of shock, not because my dick was hard and pointing at him but…
Jeremy was wrapped around his Grandma’s boyfriend’s finger, and while Ted had introduced Jeremy to many things, he had withheld the thing that Jeremy wanted most.
Jeremy didn’t want it at first but as the nights went on he started to change his mind, especially after when he got the chance to witness his grandmother and how she reacted when at the receiving end of Ted’s massive manhood.
Tonight, Jeremy was to learn, was the night.
Ted had asked me to join him in the cellar after the TV had gone off under some phony pretense of helping him find something he wanted, so I followed him down the steps.
“I told your Grandma my back was bothering me. Don’t worry, it isn’t,” he assured me. “That means she won’t be waiting for me to fuck her, so we can go right to your room after her bedroom light goes out, okay?”
“Okay. Uh… Ted? I want to show you something,” I said while undoing the knot in the robe I was wearing, and after it came loose I let the robe slide off my shoulders.
I looked at Ted’s expression when he looked down at my crotch. It was one of shock, not because my dick was hard and pointing at him but for the gardening I had done earlier in the evening.
“You said you liked…” I started to say but he waved his hand to stop me and then brought that hand down to run his fingers over the pink smooth skin above my cock.
“Beautiful,” Ted said as he took a deep breath. “Thank you.”
“I shaved it twice to make sure it was smooth.”
“It is,” Ted said, and then his eyes sparkled even more when I put my hands behind my head to show him that there would be no more plucking the hairs from under my arms because what he hadn’t extricated manually already had fallen under the blade.
That was the tough part, because I had waited so long for the little hair I had to grow to begin with. After shaving my armpits smooth I looked at what I had done. Come college, if I had a roommate it might be tough to explain why I didn’t have a hair on my body below my head. I only hoped Ted would like it.
“Thank you,” Ted said as he bent down and let his tongue slide over the smooth skin, and without the hair the sensation was even more intense.
“I want to tell you something Jeremy,” Ted said before we headed back up the stairs. “I’ve done this before, many times. What I mean is that I’ve dated women who have children, although when I was younger they would be the woman’s sons instead of their grandsons.”
“When I would find the fellows interesting, I would do with them what I did with you. Seduced them,” Ted elaborated. “I wasn’t always successful, but you would be surprised at how few times I was rebuffed.”
“You’re kinda persuasive,” I threw in.
“I know. I do have a particular preference for the sweet and submissive types like you,” Ted confessed. “Anyway, I just wanted to tell you that I’ve never ever wanted any of them as much as I want you.”
With that Ted hands cradled my face and leaned forward to give me a kiss, which shocked me.
“Let’s go upstairs,” Ted suggested.
“Ted?” I asked. “This is going to hurt, isn’t it?”
“I can give you two answers to that, Jeremy. The first would be to say that of course it won’t,” he stated. “The second answer would be to tell you the truth.”
“I thought so,” I nodded as I admitted I was scared.
“I know,” Ted said. “That’s part of what makes it good. It will hurt, although I will try to be gentle at least at first,” Ted admitted. “After I get going though, I confess that sometimes I lose control of myself when I feel my cock getting crushed by a tight young ass like yours.”
I nodded again and after putting my robe back on I followed Ted upstairs. After we got to the kitchen Ted looked down the hall. Grandma’s bedroom light was already out and so we headed the other way down the hall to my room.
“Come to me Jeremy,” Ted said after telling me not to turn off the light, and so I went over to the bed where Ted was holding that 6″ purple vibrator that I had watched him use on Grandma before he impaled me with it.
“Get on all fours for me Jeremy,” Ted instructed. Present your gift for me.”
My gift was apparently my anus, and as I got me knees on the edge of the bed I braced myself with my hands as I felt Ted’s greased finger slide inside of me. What had hurt so much at first was now a pleasurable probe and I groaned as Ted corkscrewed into my bowels while preparing me for the purple toy.
“Oh Jeremy,” Ted sighed as he pressed the rubbery toy against my puckered ring. “Remember how excited you got when you saw me use this on your Grandma? And how you were so scared when I first put it in you?”
“It hurt at first,” I grunted as Ted slipped a little bit more into me.
“But now you like it, don’t you son?”
“Uh – Yes,” I choked as I felt the vibrator slide all the way inside me, and as I braced myself for when Ted would hit the switch I asked him, “You are going to do it tonight, aren’t you?”
“Do what Jeremy?” Ted teased. “Tell me.”
“You’re going to put your dick in my ass, right?”
“Yes Jeremy, but we have to get you ready first,” Ted said as he hit the switch to get that toy undulating inside of me. “How’s that?”
“Good,” I grunted.
“Remember when I told you this was one of a set of three?” Ted asked me from behind. “This is the little one.”
Ted threw a smaller version of what was inside of me on the bedding in front of me, one that was even smaller than my dick.
“You wouldn’t have any need for that, would you?”
“No sir. This is good,” I managed to say between gasps.
“Now this one,” Ted said as something got tossed on the bedding in front of me, and as I looked in horror Ted continued. “I think you’re going to like this one even more. After all, you’re a big boy now.”
“Omigod Ted no!” I cried as I looked at the other part of the set, the big brother of the other two which might have been close to a foot long – a purple version of Ted’s massive manhood. “I can’t do that. It would split me in two.”
“Nonsense Jeremy,” Ted chuckled, reveling in my horror which was not in any way an act. “Now let’s stand you up and take a walk. Keep that toy in your ass now.”
“Oh geez,” I groaned as I took a step with that rubbery blender churning away in me, a whole different sensation to be sure. “Where are we going?”
“Do you want to take a walk down to see your Grandma?” Ted asked as he held my arm and started toward the door.
“No – please don’t,” I mumbled, the thought of Grandma seeing me with a boner and her toy packed into my butt horrifying. “Anything but that.”
“Okay,” Ted said as he took me away from the door and walked behind me until we were in the middle of the room. “Feels even better when you’re walking and trying to keep that thing in your ass You like it?”
“Yes,” I said as I felt Ted’s now naked body against my back while he wrapped his hairy arm around my neck, almost choking me in a way.
“I’m surprised you wouldn’t want to let your Grandma see how much her little Jeremy has grown,” Ted chortled, looking over my shoulder and my dick which was stiff and eager to cum from the toy shaking my prostate. “Wouldn’t you like your Grandma to see how big your dick is now?”
Ted’s mocking my very modest endowment didn’t bother me as much as it seemed to excite him, and as he kept his one hand around my neck and used his thigh to keep the vibrator way up my ass I felt his other hand come around.
“You want to cum don’t you Jeremy?”
“Yes – please.”
“You going to pop a big load for me?” Ted said as his fingers rubbed just above my throbbing dick. “You usually do.”
“Think so,” I said while my body started to wiggle like the toy.
“I’m going to reach down here and grab your dick at the base – that spot between your balls and your dick,” Ted explained. “Are you going to be able to keep from cumming?”
“No – gonna cum any second,” I warned Ted as my legs got rubbery.
“Yes, let’s see how far that little cannon can shoot. See if you can reach the closet door,” Ted said just as his thumb and index finger grabbed and rubbed the spot, and I didn’t last a second.
Ted was holding me up as my dick erupted, and as I came I heard him laughing as he kept massaging that spot while I sprayed cum all over the place.
“Please – no more,” I whimpered after my dick went limp, and Ted clicked off the toy and extracted it from my anus before hugging me from behind.
“Let’s take a look,” Ted said as he walked us over to the closet door. “Son of a gun! Look at that. Must have shot that about 5 feet!”
“I’d better clean it off,” I said as I saw the wad of cum near the bottom of the closet door drooling down the slats.
“No time for that Jeremy,” Ted said as he led me back over to the bed. “We’ve got unfinished business to take care of.”
“If you relax it won’t hurt as much,” Ted declared after positioning me on all fours on the edge of the bed. my feet hanging over the lip.
Easier said that done, I concluded as I braced myself for what seemed like an impossibility, having watched Ted lubricate the giant purple snake profusely before coming behind.
“Omigod!” I cried out when I felt the tip of the toy enter me, but it wasn’t as bad as I feared, in part because it was rather soft so instead of piercing me it sort of flowed into my bowels.
“There you go,” Ted said as he pulled it out of me. “My turn.”
No warm-up or anything. Just Ted’s cock, and this I felt as he coaxed his fully engorged shaft deep into me.
“Hurts!” I cried out.
“Ssh! Don’t want to wake up your Grandma do you?”
I bit my lower lip while ted’s cock kept going deeper and deeper into me until I could feel his balls against the backs of my thighs.
“Good boy!” Ted exclaimed, and after retracting his manhood as slowly as he had put it in, he picked up the tempo.
“Take that cock!” Ted snarled as he grabbed the back of my scalp in his fist. “Tell me how bad you want it.”
“Want it – want it back,” I grunted as my little bed slammed against the wall, creaking and groaning with each thrust.
“Your dick’s hard again,” Ted snapped as he reached around me with his free hand, but that situation changed the second he started to savagely pull on it and I shot a load onto the bedding.
Ted wasn’t done though, and after what seemed like an eternity of humping me he pulled his cock out of me. he hadn’t cum though, and only stopped to roll me onto my cock, slapping my cheek with his still swollen member before telling me to grab my ankles and spread my legs wide.
“You should see your gaping asshole, Jeremy,” Ted chuckled as I felt his fingers probing my anus. “You’re a man now. Know what I’m doing?”
“Your finger – it’s in my bottom.”
“You’re close. Try four fingers,” Ted cackled and spun those fingers inside of me as he spoke. “By the end of summer I’ll be fisting you with my whole hand and you’ll be begging for more.”
“Please what Jeremy?”
“Your cock. Put it back in me. Want to feel you cum in my bottom.”
“Be happy to oblige, but I have to warn you – I was being gentle before.”
“You were?” I asked, and for the next few minutes I learned he wasn’t kidding.
Ted was like a raging bull above me, his upper torso crimson and his sweat flying off of his body as he thrust in and out of me without mercy. When he came, filling my bowels with what felt like an ocean of cum, I was sobbing and shaking while still holding onto my ankles.
“How did you like that?” Ted asked as he climbed off of me, instructing me to stay on that position on my back with my legs akimbo.
“It was…” I started to say, but Ted hushed me.
“I wasn’t talking to you,” Ted said as he moved away from the foot of the bed, and it was only then that I realized that we were not alone.
“Grandma?” my voice croaked as I took in the surreal scene from between my spread legs.
It was Grandma, standing outside of the now-open closet door, where she had been all along I guess. She was wearing a nightie and held the hem of it up under her breasts. One of Ted’s purple toys was inside her pussy as she walked toward the bed, and she looked all rumpled and sweaty, much like I had when it was we inside the closet.
“Jeremy – I’m so proud of you,” Grandma was saying while Ted kept me on the bed where I was, and then Grandma was kneeling at the foot of the bed while Ted smiled at what was happening. “Let me make it better.”
“That’s it Effie,” Ted sighed as his girlfriend – my Grandma – put her head between my legs and after giving my deflated dick and spent balls some tongue affection, moved her mouth down lower to soothe my savaged anus. “Make it all better for little Jeremy.”