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Grandma's Got a Boyfriend Ch. 01

By: timmywells



This story ran a little long so I've broken it up into parts.

***



This was a whole new experience in this summer of 1993, because while I had been sent to spend the summer with my Grandma every year since Grandpa died four years ago, things had changed around the old farmhouse.

Grandma had a boyfriend, and I know that the term sounds funny when you attach it to a man that was in his mid-sixties like my grandmother, but that's what he was. My mother didn't know about it and I think that was because Grandma was embarrassed about it. I don't think that I would have been shipped out here had they known about him.

The purpose of me being out there was to do chores and help Grandma out, because even though the farm was no longer a real working farm like it had been, there were still things that needed doing. I never minded coming out because I loved Grandma, but things had changed.

Now there was Nick in my life, and being stuck out here for four weeks before college began would strain our already tenuous relationship even more. Nick was not going to be celibate that whole month, and by the time I got back I would have been replaced. 

It would be no surprise, since he pretty much came out and said it, but it would still hurt to be dumped. While I had messed around with guys before, Nick was the first man who I had fallen for. The only other men I had experienced had been older guys who had used me like I used them.

So when Grandma's boyfriend showed up after my Mom had dropped me off, it made for an awkward situation. Grandma didn't want her daughter to know she was in a relationship with a man, but there was no way to hide him from me. He didn't actually live there, but I sensed he spent a lot of time at Grandma's judging by the amount of his stuff in the spare bedroom I used to use.

"This is really a nicer room," Grandma had explained to me when she showed me my new sleeping quarters, a room at the other end of the house that had been empty for years.

"I would appreciate you not telling your Mom about Ted," Grandma had said to me after showing me my new room. "I'm going to tell her eventually, but I thought I would wait for a while. She might get upset, but Ted's really a nice man. You'll like him, and if we're still seeing each other come the holidays, I'll introduce him to the family."

That was fine by me, although if it was up to me I would have gone back home and spent the summer with Nick's cock down my throat instead of being stuck out here in the middle of nowhere where I was no longer really needed. Instead, I was helping Grandma keep a secret that I thought was silly for her to have, given her age and the amount of time she had been alone since Grandpa passed.

I went along with it though, not only because I loved Grandma, but because her boyfriend seemed like a nice guy. He was about 6' tall and very solidly built for an old guy. Ted had mostly grey hair and I guess in a way he looked a little like Paul Newman, or so my Grandma mentioned when she spoke about him.

He was also, at least during that first day I was there, very touchy-feely. Ted was always patting me on the back or the shoulder whenever we passed each other. I was out in the back bringing out a sack of topsoil for Grandma, and after I set it down he came over and squeezed my bicep.

"You must be a lot stronger than you look," Ted commented after checking out my muscle, and that was true because he was able to put his thumb and index finger almost all the way around my bicep, and then he slid his thumb up further.

"Say Jeremy," he exclaimed while rubbing his thumb in my armpit. "Got a little hair under your arms already I see."

I squirmed away giggling, wondering what he had expected. I mean, it wasn't like I was a kid, I was 18, even if I didn't look it. 

After he left I shook my head, more than a bit embarrassed but not only because I had a scrawny build. My dick actually tingled after Ted touched me, a sure sign that I was missing Nick already, and I suspected that this was going to be a long month of jacking off in the shower if my Grandma's boyfriend merely touching me had that effect.

After dinner that night, I took a shower, enjoying the fact that I had my own bathroom at that end of the house. That meant not having to share the other one with Grandma any longer, and just like I had predicted I got myself off. When I came I was mostly thinking about Nick, but there was a bit of it inspired by Ted. I guessed that to be inspired by Ted's arms. They were muscular in a wiry way, and covered with grey hair so thickly it obscured a couple of old tattoos beneath.

I started think about whether Ted and my Grandma did it, although that seemed far-fetched. When I pictured that scenario, it wasn't Grandma I visualized. It was Ted and those arms. Maybe it was because Ted's arms were like those of that man at the library, who insisted on giving me a ride home when it closed. That was a ten minute trip that took over an hour, but getting my first blow-job was worth it.

I made sure my spunk made it down the drain before stepping out of the shower, and after drying I put on my robe and ducked into my room. The living room was dark, so I guessed that Ted had gone home and Grandma had turned in just like she said she would went I had said goodnight.

After I put my pajama bottoms on I went out to the kitchen to get a drink, but before I went back to my room I heard some noise down at the other end of the hall. Since I had nothing to do and was nosy by nature, I went down to see what it was.

Part of my job before was to make sure that if Grandma had any need for assistance, like being ill or falling down, Mom had always told me to keep an eye out for Grandma just in case something didn't sound right. That had never been necessary because while Grandma was petite and in her mid sixties, she was as healthy as I was.

As I neared Grandma's bedroom door I stifled a giggle because on the other side of that door both of my earlier questions were being answered. Ted had definitely NOT gone home, and as for whether they did it or not at their age, the answer was a loud yes. 

"Damn," I sighed as I heard Grandma sounding like she was trying to be quiet, her little yips barely audible over the grunts of Ted and the bumping of the bed against the wall. 

I felt pathetic standing there with my hand in my pajamas, pulling on my dick as I leaned against the wood while straining to hear the guy pounding my Grandma into the headboard. If I hadn't cum a few minutes earlier I would have got myself off again by the time they finished, the end punctuated by a loud groan that had to belong to Ted.

Taking my cue, I hightailed it back to my room. Even though I was giggling after I got to bed, the fact was that I thought it was exciting to be listening to them like that. 

Take that Nick, I thought as I slipped under the sheets. You're probably getting your dick sucked by that new kid that just moved next door to you, but I'm getting turned on by listening to senior citizens screwing.

One thing was for sure. This was going to be a long summer. 

****

It was tough seeing my Grandma and her boyfriend the next morning and not thinking of them grunting and groaning the night before, but luckily they went shopping so I saw little of them. Before they went into town Grandma pulled me aside and asked me a question.

"Jeremy," Grandma said, her hands clutching each other as she looked at my shyly. "Sometimes Ted - he doesn't drive home at night if he's had a couple of beers. I hope that doesn't offend you."

I assured that it was her house and her business. Besides, I was happy that she had made a friend like that because I knew how lonely it was for her these last few years without Grandpa.

"I know I'm an old fuddy-duddy, because things have changed and all, what with hippies and free-love and things," Grandma declared, and I nodded although hippies were ancient history in 1993. 

"I'm happy that you're happy," I told her, and it was true that she seemed to be more sprightly these days. "You sure seem it."

"Oh, I sure am," she said with her eyes twinkling. "Ted's not your Grandpa, rest his soul, but he's a good man."

Having heard him last night, I was tempted to say that he sure sounded good but I bit my tongue.

****

After dinner and the obligatory watching of The Golden Girls, I said goodnight and went in to take a shower, leaving Grandma and Ted out in the living room. I decided not to jerk off, and not because I didn't want to because it seemed I always wanted to pump one out. Even when I was home and seeing Nick I would end up with my best friend in my hand at least once a day.

I don't know what the record for 18 year old guys masturbating was but I was sure that I had shattered it, and now I was planning something else for tonight. I knew the chances were good that they wouldn't be getting it on again tonight, but if they did I was going to be ready.

Sick, Jeremy, I told myself as I made sure not to scrub my cock too much in the shower. Listening to your Grandma with her boyfriend is about as sick as they come.

After leaving my bathroom I took a look down the far end of the house, and saw that there was light showing under the doors of both the other bathroom and Grandma's room. I guessed that meant that Ted was staying over, so I went into my room to get fully dried and put my pajamas on, kicking the door closed behind me.

I had pulled my robe off and was drying my hair, which because I wore it long took a while, when I got the feeling that something was wrong. I was not alone.

"Nice," said the voice in the corner, the deep tone of Grandma's boyfriend, and although there was only a night light on I could see him standing there. What was worse was he could see me quite well.

"Ted!" I blurted, fumbling while trying to pull the towel from my hair to cover myself.

"Nothing to be ashamed of Jeremy," Ted said as he leaned back against the wall, wearing a bathrobe and a smile. "You've got a bigger one than I had expected for a little guy like you." 

"What are you doing here?" I asked, not wanting to tell him that when I had gotten in the room, I had half a hard-on and was probably looking as good as I would get. Nothing like what I was hiding after it shriveled up from shock.

"Thought I'd return the favor," Ted said, enjoying the discomfort I was not able to hide. "After all, you weren't shy about coming down and peeking on me and your Grandma last night, were you?"

"I wasn't!" I insisted, and he tilted his head as if to say I was lying, which I wasn't. 

"Uh - I was listening," I confessed before adding that if I could have looked I probably would have.

"Saw the shadow of feet at the bottom of the door," Ted said. "If you're going to be a good spy make sure the hall light is off. Did you like what you heard?"

"Sorry," I said sheepishly with my towel crunched up over my crotch. "Kinda boring up here."

"Want to watch us tonight?" Ted said with a chuckle. "You can get into the closet. Your Grandma usually conks out after I fuck her, so you can sneak out then."

"NO!" I said indignantly.

"You never had the urge to see her naked? Not a bad body for a gal her age," Ted informed me. "Her tits sag a bit but she's got a tight pussy. Sure you wouldn't like to check her out?"

"Definitely not."

"Thought so," Ted declared. "You see, I've got a sense about some people. I think it's called gaydar."

"What?"

"You know what I mean," Ted said. "Certain guys I can just tell, and you? Or am I wrong?"

"I think you better leave."

"I'm going because your Grandma is getting ready for me and I don't want to keep her waiting," Ted said as he took a step toward the door. "Don't let this conversation stop you from coming down to listen though. I don't think Effie would like to know you were listening, but the idea turns me on a great deal."

I said nothing while stepping aside so Ted could get to the door. When he got there he stopped in the doorway, and after peeking out down the hall he turned around to face me.

"You sure you can't see inside her room?" Ted asked, and after I shook my head no he asked me another question.

"Want to see what your Grandma's going to get?" Ted asked me, and I shook my head no. 

It wasn't going to matter if I answered him or not because Ted's hands were already going to the knot that held the robe together. After it came loose he opened the robe wide and stood there brazenly naked beneath it.

"Don't turn away," I heard Ted say as I looked over at the wall. "Look at me. I want you to look as much as I know you want to."

"What do you think?" Ted said after my eyes went down to what he wanted me to look at. "Not bad, huh Jeremy? Your eyes look like Effie's did the first time she saw it. Guess it's nothing like what she was used to getting."

"Please leave," I whispered, still in shock over what I was being forced to look at, and Ted finally nodded.

"I expect to see your feet down there in a bit," Ted said before walking down the hall. "And after I get done sending your Grandma to dreamland I'll come back and pay you a visit." 

Ted finally left, and I went over and closed the door with my body trembling like it was cold in the room, even though it was just the opposite.

What had I done? I had gotten caught being nosy before. That was what had gotten me involved with that man in the library. I had been in the men's room peeing when than guy came in and stood at the urinal next to me. I couldn't help but take a peek over after watching his arm move. After I looked down and saw him wiggling his cock, I glanced up and saw him looking over at my dick.

But now this? This was worse. If Ted ever told my Grandma about this, she would tell Mom. Even though the chances were that he wouldn't say anything, what if he did? It would kill Mom to know her pride and joy was really a pervert.

That was a terrifying scenario, which makes the fact that a couple of minutes later I was putting on my pajamas and walking down the hall hard to understand.

****

"Ted honey," I heard Grandma whimpering after I had been outside the door for about ten minutes enjoying the rhythm of the squeaking bed thumping against the wall along with the two of them grunting. "I'm getting too sore. Here - let me..."

"That's it," I heard him grunt while Grandma tried to hush him. "Suck it. Suck it dry."

That same moan came again from Ted soon after and that was my cue to scurry back to my room. It must have been quite a sight with my left hand holding up my pajamas while I cradled a handful of cum in my right.

I paused to rinse my hand off in the sink before going into my room and closing the door before looking for the latch to secure the door. It was a lock that was not there.

"Shit," I said to no one. "What if he really does come up here?"

I killed the light and climbed under the sheets, no longer feeling like an 18 year old pervert but more like a child afraid of the dark.

***

Ted had been only kidding around. He was just having fun with me as a punishment for being caught snooping. Ted wasn't coming up here. I came to that conclusion after huddling under the sheet for about a half hour with my back to the doorway. It was time I spent looking at the shadows on the wall caused by the moonlight coming through the tree outside my window.

People did stuff like that to me all the time, scaring and intimidating me. I guess they did it because I let them get away with it. I should have just stuck my finger in Ted's chest and told him to fuck off, but when I ran that scenario through my mind it was followed by imagining Ted snapping my finger in two.

As I started to get tired and waited for sleep to overtake me, I thought back to Ted. I wasn't thinking about him and Grandma either but only him. I was thinking back to the afternoon when he grabbed my muscle, and the way he tickled my armpit while making fun of the little cluster of hair as he played with it.

Ted probably had real hairy armpits, I surmised, judging by how hairy his arms were. He sure had a hairy chest. That much I knew from when he opened his robe in the doorway, but I didn't really get a good look at his chest because when he had told me to look at him my eyes went lower.

Down past the silver cloud on his chest, and lower than the still trim stomach. Lower than the grey bush of pubic hair as well. My eyes were focused below that, and even now I could not believe what I had seen.

The man in the library had a pretty big dick, and Nick's was bigger than mine as well but Ted's was in another world. My heart was still racing as I recalled the way that absurdly long hose hung between his skinny legs while he stood there arrogantly exposing himself to me.

Who could blame him? If I had that thing between my legs I would never wear pants. It was shaped almost like a spear, thick at the base and tapering down almost to a point, probably looking that way because he was uncircumcised and seemed to have a really long foreskin.

"Wish I had a foreskin," I heard myself whispering to the shadows, adding another thing to the list of stuff I wished I had.

"Wish Ted had come up here after all," I added, but even as I said it I knew damn well that if he had showed up I would have probably wet the bed from fear.

Then the door opened.

Slowly while the hinges cried out their need to be oiled, the door opened and the hall light began to fill the room. As it did the huge shadow of the man in the doorway filled the back wall of the room I was staring at, not looking like a slender six foot senior citizen but more like the shadow of a behemoth.

Just as slowly the door creaked closed again, and for a minute I wasn't sure whether Ted was in the room or not. Then I heard the floorboards giving away the footsteps approaching the bed. The footsteps stopped and then I felt the sheet being pulled down, and as the bed bounced a little I was no longer alone on the bed.

"Waiting for me, Jeremy?" the deep voice behind me asked, and I could feel his breath on my back as well as smell the minty toothpaste.

I didn't answer, somehow hoping he would think I was asleep. Then I felt Ted's hand on my bare shoulder and heard him asking me if I liked the show.

"Tried to make it fun for you," Ted said as his hand massaged my shoulder. "I'm afraid I wore your Grandma out but she didn't fall asleep right away like usual. I think I made her pussy sore. Hope you didn't mind the wait."

"This conversation is a bit one sided," Ted said after I didn't respond, and then he added that he knew I was awake.

"What do you want?" I asked, my voice barely audible.

"You're kidding, aren't you Jeremy?" he asked. "I'm glad you aren't wearing the pajama top, but tomorrow night when I come to you don't have the bottoms on either. They will only get in the way."

"Please," I said, sounding like a sissy as Ted's had slid down to the snap on my pajamas.

"They're coming off Jeremy," Ted informed me as the snap clicked open. "It's much easier if you help me do it."

"What about Grandma?"

"She's asleep, and there's plenty of me to go around if that's what you're worried about," Ted said as his hand slid into my pajamas.

"Hmmm... you don't have much hair down here either, do you Jeremy?" he mentioned as his fingers raked gently through the modest tuft of curls above my dick. "I noticed earlier today your legs have only a little down on them as well. I love that. I'd love it even more if you were smooth all over. Young smooth guys like you are so erotic. Old hairy guys like me are so - ugh!"

I wanted to tell him that I sure didn't agree with that but while I think my lips moved no sound came out, a sign of how terrified I was.

"Like what I'm doing, Jeremy?" Ted asked as his fingers kept doing a little ballet in my pubic hair without going any lower, tormenting and teasing me while I squirmed.


Grandma's Got a Boyfriend Ch. 01



"No," I said.

"Tell you what Jeremy," Ted informed me. "I'm going to slide my hand a little lower, and if your dick isn't hard I'll go back down the hall and never bother you again."

"Please don't," I begged but by then it was too late.

"Nice," Ted sighed, biting me lightly on the neck as his fist wrapped around my dick, which was in the very condition he had expected it to be in. "You're so hard too. I can feel it throbbing. Mmm... what is it they say? Anything more than a handful is a waste?"

I groaned as his fingers worked my dick like it was a musical instrument, and then he was leaning away a bit so he could put me on my back while he reclined on his hip next to me.

Ted was smiling at me. I could see that even in the murky darkness as he let go of my dick. It slapped back onto my belly and then his hand went lower, parting my thighs so he could get at my balls.

My sac was shriveled and taut when his hand first got there but his warm grip loosened them up so he could soon roll my nuts around in his paw. That gentle kneading caused my legs to churn around in response.

"That's it. I can tell you're starting to relax," Ted said. "Nice pair of balls you've got on you here son. I'll bet they're busy making cum non-stop, if you masturbate as much as I did when I was your age. So tell me, did you like listening tonight?"

"Yes."

"Good. I wanted you to," Ted said. "Here, let me enjoy all of you."

With that Ted used his free hand to grab my wrist, bringing my hand back to the headboard while lowering his face to my underarm. As his tongue slid through the hollow and over the tiny cluster of hairs my body convulsed involuntarily, causing Ted to chuckle.

"Nobody ever did that to you before?"

"No," I answered truthfully although Nick had me do it do him all the time, and as I savored the strange sensation I discovered why Nick liked me working over his bushy pits.

"Are you like me, Jeremy?" Ted asked, and when I told him I didn't understand he elaborated. "I mean, I like girls and boys. Are you bisexual?"

"I don't know," I replied, squirming as Ted's hand kept kneading my balls. "I mean, all through school I tried to. I mean I went on dates with girls but I never did very well."

"Did you do better with the fellas?"

"Not really. I never did much with anybody."

"Just sat at home and jerked off?" Ted asked, and when I didn't answer he chuckled.

"So tell me about your first experience with a fellow."

"It was a man at the library," I explained. "He was in the men's room taking a leak and I was next to him. I kinda looked over at him.

"A pecker checker, huh? You like watching guys pee?"

"No. I'm just curious."

"That wasn't the first time you looked at a guy though, was it Jeremy? I'll bet you've looked at a lot of men in a lot of places. I'll bet you went crazy in the locker room at school," Ted correctly deduced. "I never actually knew you but I think I know you. I've known a lot of guys just like you. A lot of guys like to look, and there's a lot of guys like me too. Guys that like to be looked at. So go on with you and the man at the library."

"I left the library and as I was walking home he pulled up in a car and made me get in with him."

"Made you?"

"Well, he said to get in."

"Big difference."

"I was scared," I explained. "He took me for a ride and then he asked me if I wanted him to suck my dick."

"And you said yes."

"I didn't say anything so he just did it."

"And you liked it, didn't you? I'll bet you came right away."

"No," I confessed, and then told Ted how I was so intimidated that I couldn't get hard. 

"The man was very patient and said he would keep sucking it until I got hard. It seemed to take forever and the longer it took the more nervous I got, but eventually I got a boner. Once I did then I came real fast."

"Then what?"

"He said we should take a walk. There were some woods behind where we were parked, and when we got out of sight he told me to get on my knees and - you know."

"He wanted you to suck his cock, and you did."

"I tried but I wasn't very good at it. After a while he had me take my pants off and - ooh!"

"Sorry," Ted said, lightening the grip he had on my nuts. "Got carried away there. He had you take off your pants? He wanted to fuck you in the ass, didn't he?"

"I didn't know what was happening, I swear," I related. "He put his finger in my rear end. It was greasy but it felt good. The next thing I knew he was climbing on me and I couldn't stop him."

"You didn't want to stop him, did you Jeremy?" Ted asked. "Did it hurt?"

"Yes, it hurt a lot but he kept doing it."

"But you liked it?"

"I guess. He told me that it would hurt less the next time."

"You met the man again?" Ted asked, and I nodded.

"Every night for about a week," I admitted.

"And I'll bet you got better at sucking cock too," Ted suggested.

"I guess."

"You still see him?"

"No, the last time we went back in the woods we got caught by a cop," I explained. "He got away but the policeman caught me."

"You got arrested?"

"No. He told me he was going to take me home to my mother, but then when he looked at my I.D. and saw I was 18, he said he changed his mind."

"What did he do?" Ted asked. Don't tell me he..."

"No," I said. "He said he wasn't interested in sloppy seconds, but he took out his dick and told me to suck it and if I did he'd let me go."

"And you did," Ted said. "And you liked it."

"I guess."

"You must have. Look how hard your dick is, and I haven't even touched it yet. Look at the way it's drooling pre-cum, and see the way the skin is stretched out so tight around the base of the glans? It's like piano wire the way it's so taut. Damn, how I wish I could get that hard," Ted admitted. "And I'll bet you want to cum, don't you?"

"Yes," I confessed because he had been working my balls over non-stop during all the time I had been talking, sometimes gently and sometimes rough. During that time I learned that no matter how rough he handled my nuts I still liked it.

"Tell me more," Ted asked. 

I told him about Nick, and the things we did and how much I loved him and missed him.

"Well, this won't be a total waste of a summer," Ted explained. "You'll have me and I'll have you, and maybe by the end of summer I'll have made you forget all about Nick and the man at the library. What was his name anyway?"

"I don't know. He never told me," I mumbled. Ted laughed at that and said I was really a little pig to do all that with somebody whose name I didn't know.

"I'm jealous of that nameless man," Ted confessed. "I would have given anything to be the first to have you anally."

"You?" I said way too loudly, but as I began to tell him that wasn't going to happen he interrupted to tell me I was wrong.

"I'm going to have you," Ted assured me. "Not tonight but one of these nights, and it will be great for both of us. For now, I think it's time for you to cum. I'm not even going to touch your dick either. See how red and angry your little rocket looks?"

I looked down and saw my dick pointing back up at me with a rope of pre-cum hanging on the tip. Ted's hand was still churning my sore nut sack below it, and just like he said, he never touched my dick.

Instead, I think he used the side of his thumb to rub the space between the base of my penis and the top of my balls, and when he did I felt what seemed like an electric charge start at my toes and run through my entire body.

I came. What might be a more accurate description? I erupted. I came so hard my head was spinning. My body jerked around violently like I was a manic marionette dancing for a perverted puppeteer, which was probably true.

Even after my dick spotted spurting, after I had ropes of semen not only all over my chest and stomach but even on the side of my face, my body still convulsed. Intense pleasure washed over my body but that pleasure became, if not pain then at least discomfort. I found myself begging for Ted to let go of my balls, which had a hollow ache that would still be there come morning.

"Boy Jeremy," Ted sighed as he looked at my cum encrusted body with the milky ropes glistening in the moonlight. "You cum hard and you cum in quarts. We're going to have a great summer, you and me. I guess I'll let you get to sleep now."

Ted climbed off the bed and started to leave but then changed his mind and came back to the bed, climbing on it and moving up to the headboard.

"Before I go, how would you like to taste what your Grandma's pussy tastes like?" he asked while knee-walking towards my face with that elephant trunk of a cock swaying lazily between his pale thighs. "Just a taste for now."

Above my face his over-sized organ hung like the sword of Damocles. The foreskin so long that the entire head of his cock was hidden, and I found myself opening my mouth for him to drop his manhood into it.

"That's my boy," I heard Ted sigh as my lips moved a few inches down his flaccid tube, and while I could see that his penis was quite thick at the base, the way it tapered down made it much easier to suck on than I had thought.

The part further down, well, no mouth was ever going to get near enough to try and handle, but I sucked on the end of that tool eagerly. So much so that to my shame Ted had to pull it out of my mouth in order for me to stop.

"Tomorrow," Ted said, playfully slapping my cheek with his cock before leaving. "I think you should take me for a walk out back. Your Grandma mentioned something about an apple tree near the creek that she used to get fruit from. I'll suggest that and you will agree. Okay?"

"Yes sir," I said and then he left, his cock swinging like a metronome as he walked.

I looked at the clock on the night stand, and to my shock saw that Ted had been in with me for a hour. My balls felt like they had been used as a punching bag and the cum on my chest and stomach had hardened like dried paste. I knew I could never fall asleep like this. I was disgusted with myself not only morally but also physically since I was sweaty and covered with cum, so I went in to take yet another shower.

Before I stepped in I looked at myself in the mirror and had to laugh because there was even dried semen in my hair. Under the spray I rinsed off, and as I very gently cleaned my balls I thought about tomorrow. I wondered whether the emotions I was feeling were those of anticipation, shame or fear. Maybe it was a combination of all three.

***

Part Two to follow



Grandma's Got a Boyfriend Ch. 02



The next day at Grandma's house, Jeremy offers to show Ted where the apple tree way out back is.

***

"This is far enough," Ted informed me after we got far enough away from the house. "You did good."

"What are you doing?"

"Getting comfortable," Ted informed me as he put out the blanket he had snuck out of the house and began to unbutton his shirt. "Take your clothes off."

"What if Grandma comes back here?"

"She won't. She's going to church in a half hour as well, so we'll have plenty of time to get better acquainted," Ted explained. "Feels so good to be out in the fresh air naked."

"I can't take my clothes off out here. What if somebody comes back here?"

"What's the chances of that?"

"What if a train comes by?" I whined, gesturing towards the rails in the distance that were used by an occasional freight train.

"I'm waiting Jeremy," Ted said calmly as he stood there naked as the day he was born, and when I shuffled my feet he shook his head. "I'm more than three times your age son. You're in much better shape than I am."

That might have been true, but I was not the exhibitionist Ted was. The man was so confident and self-assured that I didn't know what I was more jealous of, his demeanor or his cock.

Ted might have been a senior citizen but for a guy his age, his body was in amazing shape. Ted had only a little softness in his stomach, and the rest of him was lean and well toned. The silver hair on his chest sparkled in the sunlight, so thick that it was hard to see what seemed to be sizable crimson nipples below.

I ended up undressing, taking as long as I could to delay the inevitable. As I stripped under Ted's intense scrutiny my eyes kept drifting back to his cock. I had spent most of the time since last night thinking about that incredible organ. Even when we were in the kitchen with Grandma my eyes kept going back to his crotch, picturing that trouser snake wiggling around under his clothing.

Ted's cock might not have been a foot long like I had originally thought because it looked like he shaved the hair around the base. That made the base of his cock look even thicker than it really was, but even taking that into account there was no denying that Ted's cock was enormous.

That was in my mouth last night, I mused while fiddling with my belt. At least the head of it was. Was I supposed to pull the foreskin down? There was so much I didn't know, but I was getting the impression that I would be getting an education in a lot of things.

"You're such a gorgeous looking young man," Ted said. "Take your hands away. You have no reason to hide anything about you."

The man is old and his eyesight is going. That was the only explanation possible because there was nothing gorgeous about me. I was a skinny little twerp. Nick. Now Nick was gorgeous. If Ted even saw him naked like this he would bowl me over to get at him.

"That's it. Doesn't it feel good to be naked like this?"

"I dunno," I said with a shrug of my shoulders, and then Ted was walking toward me, his cock rolling from side to side with his movements.

"Just relax," Ted said as he came up to me and wrapped his arms around me. "Doesn't this feel nice?"

It did. I couldn't deny it. My face was in the crux of the taller man's neck, and the billowing hair on his chest felt as soft as a cloud against my bare skin as we embraced. Ted's hands were sliding around on my back from my neck to the base of my spine, his long and bony fingers surprisingly gentle.

"That's it," I heard Ted say as I started to do the same things to his back with my hands.

Our cocks were touching. I could feel his soft log against my dick, the contact possible because Ted was taller by almost a half foot, and it felt so good to feel that rubbery tube against my stiffening organ.

"I can feel your cock getting hard," Ted whispered in my ear as he seemed to rub himself into me even more. "You like the way our cocks are rubbing against each other, don't you?"

"Yes sir."

"Last night was special for me. Did you enjoy it?"

"Yes sir."

"Don't call me sir, Jeremy. I'm Ted. I'm your grandmother's lover and I'm also going to be your lover. Right Jeremy?"

"Yes," I whispered. "Ted."

"That's my boy. Let's go over to the blanket."

Ted took me by the hand and as we walked it didn't go unnoticed that my dick was sticking straight out and bouncing like a diving board with each step.

"Stay right there," Ted said while kneeling on the blanket and positioning me in front of him with his hands on my hips.

"You've got a beautiful penis," Ted said, his face inches away from what was nothing of the sort.

"So do you," I mumbled.

That was something stupid I said whenever someone would pay me a compliment, but those occasions were quite rare.

"I don't know about that Jeremy, but I am glad you seem to like it so much. Yours though? It's beautifully shaped. The skin is so pale, with only that one little vein going down the bottom of the shaft," Ted observed. "Your glans is perfectly formed as well, and there's so little hair that you can see every perfect inch of your manhood."

Ted smiled when my dick jerked upwards, almost like it was acknowledging the praise it was getting from the man who was only inches away from it.

"And to think I haven't even touched it yet," Ted said with a grin. "Not last night and not today either, although I've thought of little else. But you want me to touch it, don't you Jeremy?"

"Yes," I croaked.

I could feel Ted's breath on my cock. That was how close he was. His hands were still on my hips, squeezing them gently, and even though this wasn't a hot morning I was starting to sweat.

"I like to tease, as you can probably tell. I want to touch you and probably even more than you want me to touch you. It's the anticipation. As I've grown older I've come to appreciate the foreplay and the buildup, even more sometimes that the acts themselves. Do you understand, Jeremy?"

"I think so."

"Like last night. I enjoyed our little passion play so much, but nothing more than when I was standing in the doorway in the beginning before I went down to sex your Grandma. Do you remember that Jeremy?"

"Yes."

"The way you looked at my cock," Ted said softly before sending a chill down my spine by lightly blowing on my dick. "It never grows old. I so enjoy that look I get when people first see how well endowed I am. Effie? Your grandmother nearly fainted when she first saw it. I often wonder what is going through people's minds when they first see my penis. What went through your mind, son?"

"Big," I mumbled. "Never saw one that big before."

"You like men with big cocks, Jeremy?"

"I guess," I said while looking down at my cock, which had never been harder. "Wish mine was big."

"Yours is perfect," Ted said as he breathed in it some more. "It's the perfect size. Somewhere between 5 and 6 inches erect I'd say. Just the right length for the mouth to handle and it looks so hard. Look how taut the skin is around the head of it."

"I know," I said.

"And you want me to touch it, don't you? You want me to do even more than that, don't you?"

"Yes."

"I'm going to and very soon as well," Ted informed me before smiling and ducking down beneath my bobbing boner with his tongue out.

"You're drooling," Ted said after showing my a string of pre-cum that he had caught with his tongue. "Mmm. Delicious. Last night? The way you came? That was incredible. I can't remember seeing an orgasm so intense, and the way you came! So hard and so much semen too. Do you cum like that all the time?"

"Don't know. I don't think so," I replied, shifting my weight from foot to foot while resisting the urge to scream.

"I don't think I'm going to touch your beautiful penis just yet," Ted informed me, and after he said that I actually groaned, like I did when the projector broke at the theatre one time.

"Try not to cum," Ted said as he moved his face a little closer. "At least not right away."

My knees turned to jelly as the older man's tongue flicked at the dripping tip before his mouth slid from the opening all the way down the shaft, not stopping until his lips were at the base of the shaft and my balls were against his chin.

"OH!" I cried out as I felt the sucking sensation test my self-control.

It was like he was trying to suck my penis right down his throat, and just when it felt like I was going to make this the briefest head in history I felt Ted's hand wrap around my balls and squeeze the top of my sac hard.

"You like these handled rough, don't you Jeremy?" Ted asked after he took my dick out of his mouth.

I didn't answer and didn't even look down because it felt like Ted was twisting my scrotum into a knot down there. If I had answered I would have said that I did like it, even though I would never have thought it would.

"Your cock is drooling like a leaky faucet," Ted cackled, and when I looked down to see I saw that Ted may very well have twisted my sac in a knot, but the sight of my balls looking like they were going to burst from the stretched skin got my attention.

"You want to cum so bad," Ted sighed before leaning forward. "And I want to taste it."

It was over in an instant but just like last night the actual orgasm seemed to last forever. My legs turned to jelly as my dick kept jerking in Ted's mouth, sending what seemed like an endless staccato of cum down his throat. 

Ted didn't even blink as I blasted my seed down his throat. In fact, even after I stopped cumming and went limp in his mouth he continued to suck on my dick in an attempt to siphon every drop from my balls.

"Oh man," I said as I looked at Ted with glassy eyes, wondering how the man had managed to cause me to have two of the most intense orgasms I ever had.

"You liked that, didn't you Jeremy?" Ted asked as he rose to his feet. 

I nodded as Ted's hands went behind my neck and brought my face to his chest.

"Suck on my nipples," Ted said, and I borrowed my face into the thick belt of hair and found his bud.

"Nice," Ted sighed as he brought my face back and forth between his nipples.

It was nice for me to, not only because I reveled in the feel of his hairy chest against my face but also because down below our cocks were rubbing against each other. The feel of our flaccid cocks touching was erotic, and when I looked down I saw that it looked even better.

Talk about perspective, I mused when I looked at the absurd difference in size between our organs. Although my initial reaction was shame about how pitiful my pale dick looked next to Ted's massive beige hose, it began to turn me on for some reason. 

"Why don't you get a better look?" Ted suggested as his hands applied pressure on my shoulders to ease me down to my knees. 

I reached up and took Ted's cock in my hand, stunned at how heavy it was. I brought my other hand into play to better handle the rubbery snake, and as I brought it to my mouth the foreskin slid back a ways, exposing the crimson tip of his glans.

"That's it, Jeremy," I heard Ted sign as he ran his fingers through my hair. "Suck that cock. Make me big and hard."

I looked up at Ted while the only thing that went through my mind was, are you kidding? Make you big? I had my hands on the shaft of this enormous penis like it was a baseball bat, and as I slid my mouth down my lips barely grazed my fingers. Maybe this thing would be a foot long when he got hard.

Maybe I wasn't that good a cocksucker, because after a couple of minutes I had only noticed a slight increase in firmness. Ted took my cock from me for a minute, lifting it up and away from me.

"You're doing fine Jeremy," Ted said, explaining that he wanted me to suck on his balls.

The undercarriage of his cock was a maze of veins and skin and I did a double take when I first saw his balls. His sack was incredibly long wrinkled pouch, but when I grabbed his scrotum I learned that the nuts inside weren't much different then my own.

"That's my boy," Ted sighed as I took a musky orb in my mouth and sucked on it obediently.

I felt something on the top of my head. Ted had dropped his manhood on the top of my skull and was rubbing my hair on it, and while it probably looked goofy I was having too much fun sucking his dangling nuts to care.

When Ted had enough of me working on his balls, he presented his member to me again, and in the interim I could feel his cock had gotten stiffer. Mercifully, it had not gotten much thicker or longer, but the firming up had made his cock much easier to handle. Totally limp, handling his penis was like wrestling Jello.

With my fist squeezing the shaft tight, my mouth slid up and down the rest of Ted's cock. As I got more confidence in what I was doing my speed increased, but while my lips slid about halfway down his member and I looked at what I was holding a chill went down my spine.

Ted is going to put this in my ass. He said so last night, but looking at what I was holding it didn't seem possible. That man from the library had hurt me when he put his in me and his was nothing like this. This would split me in two.

Ted's hand were on the sides of my head while my mouth kept working up and down his fully engorged organ. He had been trying to coax my lips further down, but the tip of his dick hitting my throat would make me gag a little so he just ran his fingers through my hair.

"I'm going to cum soon, Jeremy," Ted informed me, and while I loved what I was doing my mouth was getting a bit dry and my jaws were starting to ache. "You're going to take my seed, aren't you."

I tried to nod, which isn't easy to do when you've got about 5" of cock in your mouth, but I must have communicated because Ted groaned as I felt his cock pulsate just before my mouth filled with his cream.

His cock didn't seem to spurt like mine did, but his cum flowed freely. So freely that some trickled out of the corners of my mouth despite doing my best to swallow all I could.

As I felt Ted's cock start to deflate he took his cock from my grasp and started to pull on it hard while telling me to keep my mouth open. He was milking himself so hard I could see the skin stretch down at the base as he tried to coax the last few drops out.

I could the last bead from the tip just before the head tucked back inside the shroud, and then Ted came down to the blanket with me. We rolled onto our backs and looked up through the branched of the tree above us for a while.

It was going to be a nice day, Ted mentioned as the clouds floated across a deep blue sky, and then he looked over on his side to face me.

"Oh!" I yelped when Ted plucked a hair from under my arm.

I had my hands behind my neck, but when I tried to lower them Ted clamped my elbow back up by my head.

"Don't be a baby," Ted scolded me as he plucked another hair out. "It doesn't hurt that much. I was with a young man who loved it when I did it to him. You would look even cuter without the hair. Maybe I'll pluck a couple every day, so by the end of summer you'll be nice and smooth. Maybe by the end of the week seeing how few there are."

"I'll do it to you too. See how you like it," I said, but Ted shook his head.

"No, I don't like hair on my lovers but I enjoy being hairy," Ted explained. "Does that make sense? No? Oh well. Anyway, you like hairy men, don't you?"

"I guess," I admitted.

"Nothing wrong with that," Ted said. "Now, about tonight."

I cringed at those words while my eyes went down to Ted's flaccid cock which hung down to the grass, but when he was referring to tonight he had something else in mind.

"I can't do that," I said.

"You can and you will," Ted informed me. "And you will like it."

***

Part Three to follow 



Grandma's Got a Boyfriend Ch. 03



It had been a hot day and hadn't cooled off much during the evening. Grandma's house didn't have air conditioning so the place was usually a little uncomfortable on nights like this, even with the presence of fans all over the place.

I was dripping wet even though I was only wearing pajama bottoms. Sweating like a pig even though the PJ's were made of lightweight fabric. I was perspiring so much they were stuck to my skin, and my mouth was getting so dry that I was tempted to suck the sweat out of them. I would have given anything for a drink.

The problem was that I was unable to move, and the reason was that I was standing in my Grandma's closet. Standing there just like Ted had told me to do over in the side of the closet he had cleared out for me, looking through a raised slat in the louvered closet door.

Ted was standing there in the middle of Grandma's bedroom as naked as the day he was born, smiling and looking in my direction while pulling on his limp cock. From next door I heard the sound of a sink running and then being turned off.

That was Grandma in there getting ready for bed. Poor Grandma. I felt like a pervert. I kept telling myself this wasn't my idea. It wasn't my fault. Ted made me do it.

"You'll like it," Ted had informed me. "You liked to listen to us fuck. Just think of how much better it will be to stand in there and watch us in action. I'll bet you end up jacking off."

"What if she opens the closet door and sees me standing there?"

"She won't. I know her routine, but if she makes a move towards the closet I'll tackle her," Ted explained. "Believe me when I say that I don't want her seeing you in there anymore than you do want to be seen. I think you'll be surprised at your Grandma. She's not the same woman behind closed doors."

Maybe not, but it was hard to picture little Grandma Effie acting anything like how Ted had said she did. I had protested this violation of Grandma's privacy at first but Ted was not moved by my argument. At his direction I had run down to Grandma's bedroom and let Ted put me in the closet after she went to the bathroom, a closet which was stifling hot with zero air circulation to boot.

"You like to keep me waiting, don't you Effie?" Ted's voice declared as he trumpeted the entrance of Grandma into the bedroom.

This is sick. I felt dirty as I watched my poor Grandma come over to Ted, wearing her long nightgown that looked like something that grandmothers always were on TV. Covered from neck to toe.

"Good things are worth waiting for, aren't they?" Grandma asked with a giggle as Ted swallowed up her little body in his arms.

"They sure are," Ted said, moving her around so he was behind her giving her a bear hug.

He had positioned Grandma so they were both facing the closet. It was like he was putting on a play, a play with an audience of one. One sweaty kid staring through a closet door slat at his Grandma who was getting mauled by the same guy who had sucked my cock earlier in the day.

His hands were everywhere, pawing my Grandma though her nightgown while she leaned back into him and practically swooned. 

"Aren't you going to turn the light off?" Grandma asked as he began lifting the nightgown off of her. "At least dim it?"

"No," Ted said as he looked straight ahead at the closet. "You look so hot I want to see you when we fuck."

"Flatterer!" Grandma said, her voice muffled as the nightgown went over her face.

I wasn't going to look. I had told myself that all day because the thought of looking at a naked 65 year old woman was not appealing to me at all. The fact that the senior citizen was my own Grandma made it worse.

I couldn't help it though. She was right in front of me. I had onlt one seen other live woman naked before. My mother. I had been curious so I peeked at her one time when she was dressing, and to be honest Grandma had a better body.

Mom had way bigger tits, but other than that Grandma's body was in much better shape. Grandma was only about 5' tall and couldn't weigh 100 pounds soaking wet, so there was very little meat on her bones.

The waist was a little fleshy but other than that she was as shapely as a woman her age could be. I was surprised at Grandma's breasts, which looked nothing like I had pictured her dressed.

Grandma's tits weren't large; the pale breasts were slender tubes that hung down to her waist, with large auroelas and plump nipples. I think they called them banana boobs, and Ted was making a production of showing me how pliant they were.

"Ooh!" Grandma moaned as Ted mauled her breasts from behind. 

Ted treated Grandma's drooping orbs as roughly as he had my balls the night before, and just like I had then Grandma seemed to be reveling in his brutality. Ted even grabbed Grandma's nipples and lifted her tits with the pegs in his fingers so the breasts pointed straight out, stretching the loose cones as far as he could.

"I want to fuck you so bad!" Ted sneered while looking at the open slat to where he knew I was watching.

"You mean you want to fuck me so good, don't you?" Grandma giggled as he leaned back to try and kiss Ted.

Grandma doesn't have any hair between her legs. I had been so caught up in everything else that I hadn't noticed that. Mom had a big bushy triangle of hair around her pussy but Grandma's was bald and the absence of hair made her pussy lips look large. Large and moist.

"It would be even better if you let me fuck in you in the ass," Ted suggested.

"No it wouldn't!" Grandma yelped playfully. 

"How about giving me something else I like then?"

"Now THAT I'll do, because you know I love doing that!" Grandma declared, and with that they went to the bed.

Ted went to the night table and pulled out a purple plastic fake dick which hummed and undualated when he hit a switch. Grandma was on her back waiting as Ted put lube on it.

"You like this toy, don't you Effie?" Ted said as he knelt between Grandma's spread thighs while sliding the vibrator into Grandma's pussy.

The bed was positioned so I had a side view of them so as a result I didn't see the thing go in, but by the way Grandma reacted she certainly did like it.

"Oh yeah. Put it all the way in. Get me ready for that horse cock of yours," Grandma grunted, and although I cringed when I heard Grandma talk like that it was also erotic in a way.

"Come on Teddy," Grandma said while Ted jiggled the part that was outside her pussy. "You going to make me beg for it? Get up here so I can toss your salad!"

I had no idea what Grandma was talking about but after Ted knee-walked up toward the headboard, I figured it out. Ted was holding the headboard and giving me a cocky look as he straddled Grandma's head and lowered himself onto her face, cackling while imploring her to get that tongue in deep.

It was all too surreal. My Grandma; sweet, adorable pie-making church-going widowed lady, was licking Ted's asshole. Not being forced to do it either. She had nearly begged for it, and the sounds she was making from Ted's ass-crack sounded like a pack of wolves tearing into a deer. 

As for Ted, he was riding her like he was on a horse and her face was a saddle. He had taken his hands off of the headboard and was pulling on his cock, occasionally looking in my direction while he ground his ass into her face.

Poor Grandma. Her face was jammed in Ted's ass-crack, licking at what was probably a funky and hairy balloon knot and now Ted was howling, "Yeah Effie. Get that tongue of yours in there deep!"

"Ssh! You'll wake Jeremy up!" I heard Grandma muffled plea from below, but it didn't stop her from what she was doing.

Ted was now hard and he had stopped jerking himself off, content to hang onto the headboard and let his monolith sway out in front of him until he finally declared it was time.

"Give me the real thing Teddy," Grandma cackled as she pulled the purple toy out of her and let Ted climb between her pale skinny thighs, her face flushed and her eyes looking like they had when I coaxed her onto the roller coaster at the county fair years ago.

"Ooh! Your pussy is so tight," Ted declared as he dipped the tip of his dick into her. "Like a little virgin." 

"Damn!" Grandma hissed, her face twisted as Ted pushed more and more of himself into her. "Never going to get use to how fucking huge you are!"

"And you love it you little slut," Ted snarled in response as he eased even more of himself into Grandma.

Hearing Grandma curse was no less weird than watching Ted impale her with his mammoth cock, and while I couldn't see the insertion I was able to see from the side that he only had about half of that log inside her.

Eight minutes later it was over. I knew that by the clock on the night table. Eight minutes of watching Ted treat my Grandma like a rag doll, moving her petite body around in a variety of positions for what I believed to be all of our benefit.

The one position I knew he did for my benefit. He had Grandma on all fours while he took her from behind, allowing me to see her face while he slapped his cock into her hard and fast. Her slender hangers swayed around wildly underneath her, practically rubbing against the sheets below as they flopped around.

"You're my little puppy, aren't you Effie?" Ted sneered as he grabbed a handful of her short grey hair and pulled her head back. "You had enough?"

"Less talking - more fucking," was Grandma's reply, coming out like a hiss and a challenge that caused Ted to laugh and throw her on her back for the grand finale.

Grandma had cum twice, the first one making her arch her back off the bedding while her face made like that painting "The Scream". She didn't make a sound, but I wondered whether she would have if I were not in the house.

Ted had cum once, which made him the loser if this was a contest. I don't know how many times I came, probably because by the end I was almost delirious. I was light headed and my mouth and throat were beyond parched. All I could think of at that point was Grandma please go to the bathroom like Ted said you always do after you make love.

It took a few minutes before Grandma slowly rolled off the bed, her usually pale skin flushed and red. As she stood up I could see the semen oozing out from between her reddened pussy lips and she was walking funny as she waddled to the bathroom.

"Well?" Ted asked with a leer as he opened the door, and then laughed when he saw me stagger out into the bedroom.

I said nothing as I lurched out of the closet like an extra from a George Romero movie, moving past Ted and hurrying down the hall while praying I didn't collapse from dehydration.

When I got to the bathroom and saw myself in the mirror, I could see why he thought I looked amusing. I looked like I just come out of a pool, and my pajamas were heavy with cum and sweat. After drinking many cups of water I got into the shower with my mouth open for more, and a more refreshing shower I had never experienced.

In bed afterward I thought about what I had just witnessed. I had been aroused, so much it was embarrassing to me. I was even aroused by Grandma, mostly about the way she talked and acted, although watching her was not as unpleasant as I had feared.

I also knew that as much as the thought frightened me, when Ted wanted me I would let him take me. I would let him do whatever he wanted. Anything. I wanted to be like Grandma, at his mercy and unable to resist his magical manhood.

***

The next day was awkward from the start. Looking at the two senior citizens puttering around the kitchen while I sat there eating my cereal and trying not to look at them without seeing them naked.

"Are you coming down with something?" Grandma had asked when she first saw me. "You look pale."

"I'm okay," I replied. "Didn't sleep very well."

"It was hot in here last night," Ted suggested while winking at Grandma, which caused her to stifle a giggle.

"Do you want to go into the city with us?" Grandma asked. "We're going to the mall."

"No, I think I'll hang out here," I said while grabbing at the chance to not have to look at Grandma.

How could she be like that? The things she said and the things she did were disgusting. She was just like - just like me.

"See you later," they both chirped as they left, with Ted adding a "much later" with a wink for good measure.

Tonight was apparently the night.

***

"Good boy," Ted declared after he pulled the sheet off of me later that night and saw that I was naked. "Did you like tonight's performance?"

"It was okay," I mumbled.

"Not the same as being in the room though, was it?" Ted asked as he rolled me onto my back.

"How did you manage to talk my Grandma into doing those things?" I asked.

"Didn't believe what you were seeing, did you?" Ted asked as he brought my hands back over my head.

"What are you doing?" I asked as I felt something cold and metallic click around my wrists.

"Having fun," Ted said while facing me on his side, and as he plucked a couple more hairs from the diminishing wisp under my arm he seemed to revel in my discomfort. "As for your Grandma, Effie wasn't as sweet and innocent as you thought even before we got together, so I can't take all the credit. What was your favorite part?"

"I dunno," I replied while looking at the purple toy that Ted was lubing up. "What's that?Grandma's thing?"

"No, she outgrew this one pretty fast," Ted explained. "It was a set of three and this is the little one. You saw the middle-sized one in your Grandma last night, and there's another one that's much bigger. Haven't used that yet. Would you like that?"

"No. What are you going to do with that?"

"Now what do you think I'm going to do with it?" Ted chuckled as he got up on his knees and spread my legs.

"Are you going to do it?" I asked with a trembling voice.

"Do what?"

"Fuck me in the ass?"

"I'm not but this is," Ted informed me as he waved the vibrator. "I'm just going to have some fun with this sweet ass of yours tonight. When I come in to fuck you in the ass, it will be on a night when I don't do your grandmother. I'm afraid I would never be able to get hard enough to get it in you otherwise. It's going to be tough enough - and look at that. Beautiful!"

Ted was examining my anus both visually and with a greased finger. The tip of his finger began by rubbing the puckered ring before probing a little ways in. From there, Ted slid his long bony finger as deep into me as he could, spinning the digit in and out while I writhed on the bedding.

"Such a beautiful ass. It looks like nothing had ever gone in or out that little pink ring," Ted claimed. "Have you ever looked at your anus? You know, with a mirror or something. You should, Jeremy, because it's magnificent. Trust me I've seen a lot of them."

"OW!" I yelped after I felt something clamp down on my balls, and while I couldn't see all that well it looked like Ted had put something around the top of my sack.

"Relax Jeremy," Ted said as he continued to skewer my rectum with his finger while scraping my suddenly taut nut sack with his fingernails. "Feels good doesn't it?"

I didn't answer although I guessed that the way my dick was curled back up and looking at my face was sort of an answer. Ted's finger came out of me and that hand reached down for the greased purple vibrator with the gently undulating tip.

"Yesss," Ted hissed as he gently eased most of the 6" inch toy into me, and as for me the sensation of that thing wiggling inside of me had me squirming and thrashing in the handcuffs. "I thought you'd like that.

Like an artist looking at his creation, Ted beamed down at me while kneeling at my side. His hands free, he used his left hand to stretch out his limp cock while using his right hand to twist my nipples and pluck another hair out from under my arm.

"So hard," Ted sighed as he let go of his dick to grab mine. "This is the first time I've touched this with my hands. Perfect. So hard that I can feel it pulsating in my fist. And you want to come already, don't you Jeremy?"

"Yes," I gasped while looking at Ted's hand wrapped tightly around my cock, with only the tip showing above his fist.

"No. Too soon," Ted chuckled. "You know when I asked you about anything that was your favorite thing from the show last night, I was hoping that you would have mentioned the rimming your Grandma gave me."

"It was gross," I moaned as my bowels continued to get tickled, although that was a bit of a lie on my part.

"Never did anything like that with anybody?"

"No."

"It's an incredible feeling," Ted informed me.

"Are you - you going to do that to me?" I gasped, unable to stop squirming.

"Heavens no," Ted said as he let go up my dick, and after my boner slapped back down he started knee-walking up to the headboard. "I have a better idea."

"NO! Please don't Ted," I whimpered when I saw what he was going to do. 

"Don't whine, Jeremy," Ted said as he climbed over me so his feet were against the headboard. You saw how badly your Grandma wanted to do."

"But I don't want to," I pleaded as Ted straddled my face, taking the opportunity to rub his cock and balls over my face a few times as he positioned himself the way he wanted.

"Know your role son," Ted said as he eased down onto my face.

It was all a lie. I think I had wanted to do this ever since I saw him do this with Grandma. I wanted my face to be where Grandma's was the night before but I could never admit it because it would show how depraved I had become, and now it was happening. Being forced to somehow made it alright.

Sensory depravation. That was my initial reaction as my eyes and ears become blocked by the pressing of Ted's flesh around my face, but that wasn't exactly true because there was nothing impeding my senses of smell and taste.

As I watched Ted's ass easing down and I saw where my mouth was going to be, I saw that it was every bit as hairy as I had guessed. Then the aroma hit me. It was a cocktail with a wide variety in the potion. Ted's crotch reeked of pussy, cum and sweat from being with Grandma, but then the ass cheeks opened up and overwhelmed me with the powerful fumes while my tongue burned with the tart taste of Ted's ass. 

I guess he was clean although I had nothing to judge it against, but even though I couldn't see there was no mistaking where my tongue was. Ted was riding my face like he had Grandma's and much to my shame I not only didn't resist but instead lapped like a puppy at the furry ring and when the tip of my tongue found the opening I pushed it in.

My dick was screaming for relief despite the discomfort I felt with whatever that Ted had clamped around my balls, but I kept trying my best to do as well as Grandma had. Ted's balls were scraping my neck and chest as he rocked on face and by the way he was moving I suspected that Ted was jacking himself off while I rimmed him.

That suspicion was confirmed when I heard a main groan from above, and after that moan I felt warm fluids dropping on my chest and stomach. Ted mercifully climbed off my face and looked down on me with a pleased expression.

"You love ass every bit as much as your Grandma does," Ted opined, and I nodded but I was in distress.

"Please Ted!" I practically sobbed, the effect of that vibrator whirring around in my ass combined with my nuts in something that obviously kept me from cumming making me almost delirious.

"Oh yes. Jeremy wants to cum, doesn't he?" Ted smiled while joining me in looking down at crimson dick pointing at us.

I couldn't see my scrotum, which was probably just as well if the dull ache was any indicator of what they looked like. Ted could see them though, and after he got down there he scraped his fingernails on the very taut skin before easing the vibrator in my all the way.





Grandma's Got a Boyfriend Ch. 03



"I think it's time for me to let you cum, don't you?" he asked in a grandfatherly tone before grabbing the base of my organ firmly with his thumb and index finger while releasing the noose from my balls.

It reminded me of what happened one time when I was a kid and poked inside the toaster with a fork to get a English muffin out, only this went through my entire body. I might have screamed because Ted was hushing me, but I don't remember.

I do remember the way my cock erupted like a little volcano, spurts of cum flying straight up toward the ceiling, and when it started it would not stop. I was bouncing around like a puppet, sitting upright and then slamming back down into the sheets like Linda Blair in the Exorcist.

The orgasm that hit me like a freight train ebbed for a moment, but Ted kept massaging the base of my dick and it started spurting again. The saying about something feeling so good that it hurts certainly hit home at that moment.

I finally managed sit up and grab Ted's wrists with my cuffed hands and begged him to stop. He was smiling as he nodded, and then he eased me back down and stopped doing whatever he was doing.

"Magnificent," Ted exclaimed as he contented himself with lazily pulling on my dick as it went limp, stretching the thing as far as he could to squeeze out every drop.

"Are you okay?" Ted asked as he slowly extracted the vibrator from my ass, and then put a couple of fingers into what felt like a gaping hole.

Five minutes later, when Ted had left and I was able to get up on my rubbery legs, I looked at myself in the mirror. My face was still crimson, streaked with sweat and tears, and my balls looked swollen still.

"Tomorrow night," Ted had said before leaving. "I think tomorrow night will be the night."

***

Part four to follow



Grandma's Got a Boyfriend Ch. 04



This is the conclusion of the story. I apologize for the delay because I thought I had submitted this before taking some time off from writing, but apparently I hadn't. Thanks for your patience and thanks for the folks who wrote and asked about where the end was, which brought my screw up to my attention.. 

***

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."

"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."

***

End of "Grandma's Got a Boyfriend".

thank you for reading