My name is Anthony, I am 41 years old living a pretty normal life with a wife and two grown up children, 18 and 19. Let me tell you about my experience with my dad and grandfather as a young man.
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My memories of my early life in what most would consider to be a poor neighbourhood are fond memories. Idyllic isn’t a word normally associated with the part of town I grew up in but thinking back it had everything I needed. All my best friends lived on my street, my school was within close walking distance, as were the shops, there were two huge parks close by and there was even a library: it was a great little eco system. perhaps I have my rose tinted glasses on but my childhood through to my late teens was perfect to me.
January 1998 came and I turned 18, this was when things began to change. Even though I was still living at home with my mum and dad, my carefree days felt like they were well and truly over, suddenly there was an expectation to “grow up,” get a job and do all of that.
Out of the blue my grandmother had a serious stroke and soon after passed away, leaving my 70 year old grandfather widowed and alone. As he wasn’t able to fully look after himself properly, my parents decided that we should move house closer to him to more conveniently be there to help him with certain things like cook his meals and do his laundry, keep him company and take him out from time to time. My grandfather was a cantankerous old so-and-so who was horrible to my grandmother towards the end of her life: I think he took out his frustrations on her, so I wasn’t particularly thrilled to be moving near him.
We moved into a flat very close by his on the same street. It wasn’t that far away from where we were living before, but this was before the days of internet and social media, and so gradually I lost regular contact with the friends I’d grown up with.
For the most part my grandfather was content in his own company in his flat but everyday my dad would cook his meals at our house and it fell to me to take them around to him. Rather than take them from me at his door, he would have me walk it right in through his house to the kitchen and place it down for him. This became a monotonous daily routine that after a while I started to resent.
Estranged from my friends, not yet working and lumbered with this daily chore, I became quite an isolated individual, what you might call an “Incel” these days, just in my room listening to music, playing video games, and cultivating taboo sexual fantasies in my head involving crossdressing and gay sex with people that I really shouldn’t be thinking about sex with. It wasn’t healthy but this is what isolation did to me.
On one particular day when I arrived at my grandfather’s house with his meal, he was unusually smiley and friendly when he opened the door to me, normally he’s quite curmudgeonly, which was part of his charm I suppose but he seemed very pleasant on this occasion.
As I entered he placed his hand on my upper back, slowly rubbing it as I passed him, and in the kitchen as I was putting the plates down on the table he was stood right up next to me engaging me in conversation with his hand on the small of my back. I sensed that he wanted me to stay, but I just headed to the door to leave. As usual he lead me out. At the door, before opening it, he gestured for me to give him a kiss on the cheek, which I just automatically did, then looking me up and down he opened the door and I left. On the walk home I was wondering what the hell all that was about!
Back at home my dad was looking at me inquisitively. “did he say anything to you?” he asked. “No.” I responded, and acted as if it was just a typical uneventful dinner drop-off.
Something didn’t feel right here, for my grandfather to act like he did, and then for my dad to ask me that, I felt something strange was going on.
Later, I was in my room on the bed with headphones on listening to music when in came my dad. “Go back round to your grandads will you?” he said to me. “What for?” I asked. “He wants you to do something for him.” “Just do what he asks you.” He added as I was getting on my shoes. This sounded very ominous.
When I got there he said that he wanted me to move a wardrobe closer to the wall: he’d just recently had a new carpet fitted and the wardrobe wasn’t quite back in it’s original place. With my skinny arms I grappled it and began to manoeuvre it backwards as he watched. It wasn’t particularly heavy but it was flimsy and liable to break. I opened the wardrobe and saw that it was full of clothes on hangers and shoes in the bottom. They were my late grandmothers clothes that he was keeping hold of. “We should take these out, shouldn’t we?” he suggested. So we both began emptying the wardrobe and placing them carefully on the bed.
As we were emptying the wardrobe of the clothes I was grabbing two or three at a time while he was taking them out one by one. It had been about six month’s since my grandmother died and he must have been missing her very much. He was telling me anecdotes and his fond memories that are attached to many of these items of clothing: she wore this to a wedding we went to…she wore that to a job interview, and so on.
“Aaaah yes, I remember this one.” he said as he pulled out a 1950’s Rockabilly type dress. “She wore that when we were first courting,” he recollected fondly. He held it up to me as he was remembering my grandmother in it. “She was about your age when she wore this.” He said. I thought this was really sweet. “I can put it on if you like.” I replied, only half-joking. He put this dress to one side and we continued to empty the the rest of the clothes out. With the wardrobe now empty moving it back into place was pretty easy. “I’ll put these clothes back in and I’ll be on my way then.” I said.
“You don’t have to rush off so soon do you?” He said as we were putting the last of the clothes back in the wardrobe, but with the Rockabilly one still on the bed. “I’d like to see that dress on you.” He added, picking it up and holding it up to me again. “Oh, erm, alright then.” I said, a little bit taken aback: I didn’t think he would actually take me seriously about putting it on. Right then the phone in the living room started ringing. I took the dress from him as he went to answer the telephone.
Alone in the bedroom I hurriedly changed into the dress. I felt amazing in it, it was as if my grandmother’s spirit was infused in the material and she wanted to titillate my grandfather through me.
A few moments later he returned. “Oh, you – err, I mean, that dress, does look really nice doesn’t it? just as I remember it.” he said, hoping I hadn’t noticed his little slip there.
“You don’t mind staying a little longer do you?” He asked. “No, I don’t mind.” I replied. I could tell that seeing this dress being worn was reminding him of my grandmother and taking him back to their younger days, and I was more than happy to oblige with this, it felt really sweet, and it’s not like I was doing anything else anyway.
I spent the afternoon with him in the dress just keeping him company. We were mostly just sat watching tv in silence as there wasn’t a lot that an 18 year old and a 70 year old could really talk about, but I was making and bringing him cups of tea throughout the afternoon just like my grandmother will have done, and it was fun playing this role for him. I kept catching him looking at my body and legs in a desiring way and I didn’t mind.
After a few hours it reached a point where I needed to bring this to an end and go home, as nice as it was I didn’t want to spend all night there. “Well then, I’d better be getting back now,” I announced. “OK then.” he replied. I headed to his bedroom to get changed back into my clothes with him following on behind me, which I didn’t expect.
I would have preferred some privacy to change but he stood right in front of me as I slipped out of the dress. I was completely naked as I handed him the dress, which he put back on the hanger and hung in the wardrobe. He then watched in silence as I put my own clothes back on. As I opened up my underpants and stepped into them, I smiled at him as I pulled them up but it did feel a little awkward him watching me like that. Once fully dressed I headed out of the room to make my way to the front door: he put his hand on my bum as I passed him.
At the door, before he opened it he gestured again for a kiss on his cheek. I leaned in to give him one but a millimetre from his cheek he suddenly and quickly turned his head and my puckered lips landed on his. “Bye bye now,” he said to me as I left.
Back at home I was met again with an inquisitive look from my dad. “How did it go?” he asked. An interesting choice of language, I thought to myself. “He wanted me to move his wardrobe for him.” I responded. I was there for five hours so he knew we didn’t do just that. I couldn’t help but get the feeling that my dad was in on what was going on, which is why he sent me there in the first place, like it was arranged. It was beginning to make sense. I’m sure mum knew nothing of it though. “He just needs some company every now and then, that’s all.” said dad.
I wondered to myself whether this was how it was going to be going forward: mum doing his laundry, dad making his meals and me “keeping him company” in addition to taking his meals to him.
The following day I was in my grandfather’s kitchen with him again. “Would you mind trying something else on while you’re here?” He asked me as I was putting down the plates. “I’ve left it on the bed for you.” He added. “Ok.” I said, as I went to his bedroom leaving him in the kitchen.
In his room there was an item of clothing on the bed, it was a nightie, presumably my grandmothers old nightie. I hope he’s not expecting me to spend the night here, I wondered to myself as I got out of my clothes and into this nightie. It felt really nice against my skin. It would have been below the knee on my grandmother but it was above the knee on me.
I came out of the bedroom and walked down the hall and found him in the living room eating his meal. “Hmmm, very nice.” He said. “What, me or the food?” I joked, causing him to laugh. “You look just as yummy, Anthony.” He said smiling. I sat myself down and we watched tv as he ate. When he finished, on instinct I dutifully took his plate from his lap and took it to the kitchen just as the phone rang in the living room again. He answered it and began speaking but I couldn’t quite hear what was being said from inside the kitchen. I returned to the living room just as this brief telephone conversation was coming to an end. “…Yes he is…ok then…hahaha, yes I will…ok…ok, see you soon…bye.” He was saying into the phone while looking at me. He then put down the receiver. I was intrigued but didn’t ask what that was all about.
“Can you go into the bedroom and wait on the bed, Anthony?” he asked me. Without saying anything I just went to his bedroom, closed the door and got on his bed, looked over by a photograph of my late grandmother on the bedside cabinet.
He’s too old to fuck me, surely, I thought to myself as I lay there. I was happy to give him a kiss and a cuddle if that’s what he wanted.
I watched the birds at a feeder hanging in front of his window as I laid there on the bed with the nightie rucked up a little exposing some of my smooth pert little bum and hairless legs.
I then heard my grandfather coming down the hall: the bedroom door opened and he entered. “Hmm, Very nice!” he said as he looked at me in the nightie. I noticed a growing bulge in his trousers. As I watched him undress my mind began to wander, I began imagining what my grandmother must have felt as she was in the situation I now find myself in, the excitement and anticipation she will have felt was now flowing through me. He had a decent sized cock which she must have enjoyed but it was my turn with it now. I looked at her picture again, I felt a duty to do her proud.
As he came towards the bed I moved back to give him room and he laid on his back next to me. On my knees with my bum in the air I went down and put his flaccid cock in my mouth and began sucking: I felt it grow in my mouth as he emitted hushed moans of pleasure. I raised up the nightie I was in and swung my leg over to straddle him, then let the nightie drop back down to cover my modesty. Under the nightie he was struggling to find the right place to enter me so I took his cock in my hand and guided it to the right spot myself. He then pushed upwards and the tip penetrated through, which stung a little but I could handle it. He then reached around with both hands to grab my smooth bum, pulling me firmly but slowly downwards and his shaft went into me causing me to grab his chest hair with my fingers. When I reached the bottom, sitting on him all the way in me, I grinded and circled my hips. I imagined my grandmother doing this.
“Lets have a change of position.” he suggested. So I lifted myself up off him causing his cock to spring away as I rolled over onto my back: I opened my legs really wide and he positioned himself on top of me. He then placed a couple of pillows under me which propped me up and presented me conveniently for him to enter me again. Face to face, and with a moan from both of us he plunged inside me. “Make love to me like you did grandma!” I said to him lovingly as I wrapped my arms and legs around him. He proceeded to thrust into to me. With the headboard banging against the wall I turned and looked at the picture of my grandmother again.
Right then he tensed up and started grunting: he was ready to cum. He buried his face into the side of my neck and was grinding me really slowly and deeply. “Give it to me grandad!” I begged. He then let out a loud groan as he pumped me full of his cum.
When he finished he just remained on top of me, exhausted, and I felt his cock gradually shrink inside of me.
After about 5 minutes he rolled off and laid next me on the bed. “I’m truly sorry about this.” He said regretfully. “Hmm? what’s wrong?” I responded.
“I shouldn’t have done this.”
“It’s ok, I enjoyed it.”
“Yes, so did I but that doesn’t make it right.”
Alone with our separate thoughts we both got up and dressed. After he folded up the nightie and placed it back in the draw he turned to me: “You are a lot like your grandmother, you know.” He said smiling. I held his face with my hands and gave him a kiss on the lips, then we embraced. “I think you should head off home now,” he said. I let myself out leaving him in the bedroom.
We would never make love again but going forward, I continued to bring him his dinners and occasionally spent the day with him in one of my grandmother’s outfits.
***
Now, at 41 years old I asked my now elderly father about this and he confessed that he had indeed conspired with my grandfather to make all this happen.