Helping Grandma Pt 03

I slowly opened my eyes. I could see the morning light shining down on me. I felt something pleasant, looking down at the end of the bed I saw Linda. She was sucking on my cock.

"Good morning baby," She cooed.

"Linda!" I exclaimed. "I've never been woken up like this before. It feels so good."

A few seconds passed before I got an idea.

"How about you lay on top of me so we can both suck each other off at once?" I asked.

"My my boy, I've never heard of that before. That sounds very hot." She said, getting into the sixty-nine position.

I didn't waste any time and put my face right into her cunt. Feeling her moan on my cock was something I wasn't expecting to feel so good. The vibrations hitting my head almost sent me over the edge, but I held on. I lapped at her cunt and speared her clit with my tongue. That sent her over the edge, spraying my face with her juices. Her moans and screams on my cock led me to explode in her mouth. I felt her swallow my load before letting my cock out of her mouth. She rolled off of me and onto the side of the bed.

"That was intense!" She said, out of breath.

"It was," I responded. "Your juices tasted wonderful!"

"I could say the same to you, baby,"

We caught our breath before getting out of bed. We didn't need to put any clothes on. She used the bathroom while I went downstairs. I put an apron on before starting to cook breakfast. I grabbed 6 eggs from the fridge and started frying them. I had hard fried 6 of them when Linda came downstairs. I knew she came downstairs when she came up behind me and started playing with my cock.

"I wouldn't do that if I were you, Linda. I don't want to get hurt or ruin our meal." I told her.

"Please," She said. "You won't get hurt and the food won't burn, I promise."

She pressed her body against me and jerked me off. I turned my attention to the eggs, not wanting to mess it up. Her jerking me off and kissing the back of my neck didn't help though.

I was about to blow by the time I finished them. My breath was ragged and her hand was moving faster and faster.

"Come on baby, I want to lick your cum off of this apron." She whispered in my ear.

That was when the damn broke and I stained the inside of her apron with my jizz.

"Take it off baby, I want to taste your cum for the second time this morning." She said, waiting for the apron to come off.

I turned off the heat and took off the apron. She took it from me and started licking the spots where my jizz was. Gleefully licking it all up. When she was finished, she got up and said,

"Time for my third breakfast. I love fried hard eggs."

I ate with her and we discussed what we planned to do today.

"I was thinking about going into town and doing some clothes and toy shopping. I was hoping we could go out as a couple. Would you like that?" She said, finishing breakfast.

"I would love to. We can grab new toys to try some new things! I can't wait!" I said, getting up from the table and cleaning the dishes.

She stayed at the table while I cleaned the dishes. Once I turned around she stood up and asked me, "Would you like to shower with me?"

"Of course, I would Linda!" I responded.

I walked up to her and grabbed her breasts and waist.

"I'd love to wash all of you. Especially," I stopped talking and rubbed her pussy.

"Then let's go upstairs, baby." She said, leading me upstairs.

We walked into the en suite bathroom and she entered before I did, getting the water hot and ready. When she told me to I entered the shower and began to wash her. I washed her whole body, taking special care of her special spots. Once I thought I had done enough, she took control and washed me. She washed my body and proceeded to massage my cock with her soapy hand.

"I've never gotten fucked in the shower. Could we do that?" She asked sensually.

"Yes, we can, turn around and place your hands on the wall," I answered.

I got behind her and placed my cock in her entrance. Feeling the water coming down and how sensual the idea of having sex in the shower was, I decided to take it slow, not like any of the other times we had had sex. She started moaning almost instantly.

"Oh yes baby, take me slow as this water runs down our bodies."

So I stayed at the same rhythm and made love to her. Slowly caressing her hips and breasts. I played with her nipples slowly. We stayed like that for another 20 minutes before we came together. I turned that water off and got out of the shower. I dried her off before drying myself off.

"Thank you for taking the time to be there with me. It was so erotic. I still like the fast sex we have but now and again, if you could fuck me like that, I don't think you'll be able to leave here." She said.

"Sounds good to me Linda," I responded.

"Now we should get ready for our trip to town, shouldn't we?" She said, leaving the en suite.

I left the en suite and changed into a new set of clothes. Once I was changed I went downstairs and waited for Linda. She came downstairs in jeans and t shirt.

"Shall we get going?" She asked. "And can you drive?"

"Yes, I can drive," I answered going out to the garage with her.

We got out on the road and four minutes into the drive I popped the question.

"Can you suck my cock while I'm driving?"

"I don't know baby, what if you lose control?"

"I won't I can promise you."

"Ok then," she said, undoing my pants.

I was already half hard by the time my pants came undone. I didn't say anything but I didn't think she'd do this. I was kinda shocked she accepted it so quickly. But with her soft lips on my cock head again, all my worries went away. I kept my mind on the road at all times but couldn't how good this felt. She didn't say anything she was completely devoted to her task. I let her that I was going to blow soon. And when I did she sucked up all the cum I gave her. She cleaned me off and buttoned my pants back up.

"Talk about erotic!" She exclaimed. "Anyone could've seen us. I knew you wouldn't mess up driving honey!"

"Thank you, Linda. That was the first time someone's done that for me."

"I'm glad to have been the first, baby. Now head to the mall." She told me.

I did as instructed and drove to the mall, finding a nice parking spot, we both got out and started walking around. She held on to my arm. We walked from store to store stopping and doing more window shopping than anything. We got lunch at the all and Linda asked if I'd like to join her in Victoria's Secret.

"Wouldn't we get looks?" I asked, stunned. "I mean there's an almost 50-year age difference between us. Some might even think that we're a normal grandson and grandmother."

"There is an almost 50-year age difference. And so what if we get looks, no one would think a grandson and grandmother would be a lingerie store together." She responded. "Plus, I want your input on some things."

I reluctantly agreed to join her. After we had finished lunch, we got up and made our way to Victoria's Secret. To my surprise, we didn't get any looks thrown our way. Everyone was helpful and really happy to see an older lady like Linda shopping there. I also got many compliments and even some winks about being able to satisfy such an older woman. In the end, she bought a white lace teddy, a white and black lace bra, and g strip set. And she both another lace bra, garter belt, g string, and stockings set, this time in white. She paid for the items and we left. We went to the car and she insisted on driving. I was hoping she wasn't thinking about what I thought she was thinking. My suspicions were confirmed we she pulled into the Lion's Den at the edge of town.

"Come on baby, it's no different than Victoria's Secret." She pleaded.

"Ok, I'll join you," I said reluctantly.

Watching Linda was like watching a kid in a candy shop. She looked at everything and was so surprised by their selection of goods.

"What does this do?" She asked, holding up a butt plug.

"That stimulates the nerve endings in your asshole. It's called a butt plug. Some people also use it to prepare for anal sex. Did you and Harry ever do anal?"

"No, we never did. I didn't want to be in pain and he didn't want to stick it up my "dirty" hole." She answered.

"Would you like to try?" I asked.

'Sure why not," she answered. "We've already done so much."

"Sounds great" I responded, "I'll get the lube"

I went around looking for anything else that we might want to further our sexual adventures. My eyes landed on handcuffs, a whip, a rope, and a paddle. Linda came up from behind me and asked what I was thinking.

"I was thinking of getting these to punish you when you behave poorly," I said seductively.

"That sounds interesting," She said puzzled. "People get off from pain?"

"Yes, they do. Pain can cause them pleasure. Would you like to see if you are one of those people?" I asked.

"Of course I would!" She said delightedly. "I want to try it all!"

We made one more loop around the store before she asked me a question.

"Can I ask you something, John?"

I was shocked, this was the first time I'd heard her say my actual name.

"What is it, Linda?"

"I was wondering since you are getting to do all these new things to me? Can do something new for you?"

"What are you talking about?"

"If you are going to fuck my ass, would you be ok with me fucking your ass as well?"

It was at this moment that I realized that we were right in front of the strap-on harnesses.

'Wow, I don't know Linda. I've never been ass fucked before" I responded.

"That's exactly it. Neither of us have been fucked in the ass, so why don't we experience it together?" She assured me.

"I'll do it, grandma. I trust you and I know you trust me." I told her, smiling.

We paid for all the items and left the store. In total, we had bought, two sets of small, medium, and large butt plugs, a strap-on harness, a lot of lube, a whip, a paddle, a pair of handcuffs, rope, and two reusable enemas. We drove home in silence, slowly anticipating what we were going to do when we got back.

"Can we do all this right when we get back?" Linda asked, cutting into the silence.

'Of course Linda." I responded.

I parked the car in the garage and helped her with the bags.

"Now how do we get started?" She said, stripping off her clothes in the kitchen.

"We'd have to clean our backdoors," I told her.

I followed her into the en suite bathroom.

"The instructions are pretty clear. You're going to get in the shower, I'm going to lube this up and slowly insert it into you. Once you feel full let me know and you can let the water out. We'll do this until you are clean back there." I explained to her.

"Ok, baby. That sounds easy enough." She said getting into the shower.

I lubed up the enema tip and spread her asscheeks, slowly inserting the tip into her sphincter. I felt her tense up and told her to relax, I squirted the liquid into her and waited about thirty seconds before letting it out. We repeated this process for 2 more minutes until she was clean back there.

"Now you get to clean me out, grandma!" I told her, stepping in the shower.

She prepared the enema like I did and got me ready. She repeated the process I had done to her and after 2 minutes we had finished cleaning each other out. I grabbed both small plugs and lubed them up.

"This is going to be a lot bigger than the nozzle of the enema, are you ready for this Linda?" I asked her.

'Can we prepare my ass more?" She asked.

"Yes we can," I said, lubing up my fingers. "Get your hands and knees on the bed."

She did as I instructed and I got behind her, marveling at her tiny asshole. I began to rim her asshole. She started breathing heavily immediately. I kept up the pace. After a minute of teasing her with my tongue, I pulled away and put a finger in her ass. That. Made her gasp. I teased the inside of her and pushed it in and out. Once I felt like she was ready, I pushed in another finger. This continued until I had three fingers going in and out of her. She soon told me to stop because she didn't want to cum yet.

After removing my fingers, I told her I was putting in the butt plug. She relaxed her asshole and took a deep breath as I pushed it in. At its peak, she released her breath and it went all the way in.

"Would you like to do that to me?" I asked her.

"Yes I would, I feel full like I never have back there. I'd like you to experience it as well. " She said.

I got on the bed on my hands and knees, the moment I felt her warm tongue lap at my hole I moaned. I've never been rimmed before and I don't know how people can go back after experiencing this. Once she felt like she was done eating I felt her lubed finger against my hole before she pushed it in. It was alright for a while but once she had two fingers in, she brushed up against my prostate causing me to moan.

"You like that, honey?" She asked seductively.

I nodded my head. She inserted a third finger into me and massaged that spot.

"HOLY FUCK LINDA! I'M GONNA, I'M GONNA..." I screamed before having the strongest orgasm yet.

She released her fingers and put a plug in my ass.

"It looks like you liked it more than I did baby." She told me, lying next to me. 'How long do you have to wait before we can fuck?"

"It won't take long, I just need to catch my breath. That was my most intense orgasm yet." I told her. "I was thinking we could fuck like normal before fucking each other's asses."

"That sounds like a good idea." She said.

Once I regained my composure I got on top of her and fucked her missionary for the next 6 minutes. I had a feeling the plugs in our asses had a hand in making us cum so fast. After I filled her pussy with cum I asked her if she was ready for the main event.

"Yes, I'm ready," She responded as I took out her butt plug.

I lubed up my cock and her asshole. I covered my fingers in lube and coated the inside of her asshole with it. After preparing her ass, I told her I was going in. She relaxed her asshole and I pushed in. There was a little bit of pressure trying to get my cock head in but once it passed through, there was a lot less pressure. I slowly inched further and further into her. Once I was in I asked her how she was.

"I feel so full, baby. I thought I was full with the plug but this is a whole nother level. You can go back and forth."

I did what she told me to, and began going in and out. She started moaning, that gave me more incentive to fuck her ass. She was so tight, her pussy was still pretty tight but it was nothing compared to her ass. It clamped down on the cock. I started to go faster and she started to moan more.

"I'm going to fill your ass with my cum Linda!" I cried out.

"Do it Johnny, cum in your grandmother's ass!"

With those words, I exploded and filled her ass up. I stayed in her until cock deflated and flopped out. Looking at my cum drip out of her gaping ass almost made me hard again. She slowly steadied herself and got up.

"That was quite a fucking you gave me Johnny!" She said with a grin from ear to ear. "Now can you help me into this harness?"

I completely forgot how I was going to be fucked as well. I hesitated for a second before giving in to what she wanted. I helped her into the harness and attached her dildo to it. I laid back down on the bed and got ready. She prepared me again by eating me out and lubing me up. Before fucking me she bent over on top of me and whispered,

"Are you ready to get fucked boy?"

"Yes, Linda, I'm ready to get fucked."

I felt the hardness of the fake cock against my hole. She told me to relax, and I did. It didn't help that it still stung going in. I wondered if Linda felt the same, even though she didn't say anything when I fucked her. I felt the cock head pass my sphincter and things got less painful. Before I knew it she was in. I felt full.

"You can start going in and out Linda, just take it slow," I told her.

She followed my instructions and started going in and out. The feeling started strange but soon ended up being wonderful. Each time she pushed back in the head rubbed against my prostate causing my pleasure to grow. Once she had been going for a while she picked up speed. Her going faster led on a collision course to orgasm. She was fucking my ass at the rate I fucked her ass when I came.

"LINDA LINDA LINDA! FUCK I'M CUMMING, YOU ASS FUCKING ME IS MAKING ME CUM FUCK!" I screamed I exploded on her sheets.

She pulled out of me and took off the strap-on before falling beside me.

"I think we've had enough for today. We can play with those other toys tomorrow" She said, as we fell asleep.

Thank you for the incredible feedback. I'm having a lot of fun writing these!