Chapter 4
The next day I concocted a plan for the following night when I knew my mother would be at work, and it would be just grandpa and me at the house. I was getting myself so worked up that I could barely control my anticipation. By the time my mom left, I was so horny I was about ready to burst.
I put my grandpa in the living room to watch his programs and get comfortable with a glass of wine. While he had his wine, I hurried myself to my mom’s room and found the chest behind her dresses. I pulled it out and got everything I would need for the night and spread it all out on her bed. I hopped in the shower and shaved my legs and armpits. I toweled off, and then I put my hair up in curls like my grandmother used to do. While they held their position, I donned some makeup and some of her earrings and necklace. I did my makeup just like her, as best as I could remember. I applied some fresh, double-sided tape to the breast forms and then lathered on some of the skin adhesive and let is sit and get tacky. I put on one of her bras and one of her high-waisted panties. They weren’t sexy or flattering, but I was going for realism. I positioned the forms in the bra and firmly pressed them to my bare chest. I held that position for a few minutes, and then released them. The bra supported them well, but I could still feel their weight clinging to my flesh. I bounced a little to test them out, and they held their position. I put on one of her dresses and zipped up the side, before putting on a pair of thick heels. I took out the curls and tossed my hair around. I definitely was feeling feminine and looking the part. Looking in the mirror, I was not only extremely passable, but I looked nothing like myself, and I almost looked like a young version of my mother or grandmother. Perfect!
My heart was pounding, as I walked through the house in those heels. I pinned my shoulders back and walked with my hips into the family room. I came up behind my grandpa on the couch and leaned down, wrapping an arm around his chest and pressing my cheek against his, before giving him a kiss. “Hi papi.”
“Luchietta,” he asked? “Is that you?”
“Yes, my love,” I replied. “How’s my teddybear feeling?” That is what she called him. He couldn’t really see me at this time. He could barely see all that well anyways without his glasses and with his cataracts, but I could tell he was sampling the air after finding the familiar smell of the vanilla perfume. I walked around to his side and sat next to him on the couch, right up against his leg. He pulled his head back and looked at me with confusion at first, and I almost thought my plan was about to backfire.
“You cut your hair,” he stated.
I sighed a breath of relief. “Oh yes. It is a little shorter,” I replied. “You have such a good memory.” My grandmother’s hair was down to her back, and my hair was just at my shoulders, so it was surprising what he remembered and didn’t remember. I pulled my dress back behind me and wrapped my bare leg over his knee and stroked the length of his inner thigh. We chatted for a little while, and I could see through his pants that rubbing his leg was having an effect on the bulge of his crotch. He finished his wine and leaned forward to set it on the table. “Are you getting hungry papi? I could make you some food,” I said, as I rubbed his belly. He nodded, and I got up. I came back a while later with some food and another glass of wine. After he ate and relaxed a little, I pointed to the clock and said look at the time. “Time to get ready for bed.” Little did he know that I had changed the clocks earlier, so with little fuss, I was able to get him up and get him to the bathroom to clean up.
I helped him out of his shoes, pants and out of the buttons of his shirt and then out of his undershirt. I squatted down, as I pulled him out of his pants and got a good look at his beautiful cock. My mouth salivated with anticipation, but I didn’t do anything then. I spun him around and got him in the shower. While he showered, I quickly went back into my mother’s room to change.
I quickly unzipped my grandmother’s dress and pulled it off my shoulders. I wiggled the bottom of the waist of the dress over my hips, and it fell to the floor. I stepped out of the dress and kicked off the heels. I pulled down her panties, exposing my erection in the process, before unclasping the back of the bra. I carefully took off the bra, not knowing if the breast forms would stay, but they did. They were warm from being against my body, and the fresh adhesive kept them locked into place. I really couldn’t believe it looking in the mirror. They almost looked like they could have been real. I gave them a little squeeze and jumped up and down, and they stayed in place. Feeling confident in their position, I moved on.
I went in the bathroom and found some baby oil and some petroleum jelly. I mixed the concoction and reached behind my ass and applied it to my sphincter, lathering the entrance well, working the oils into my skin. I could feel my sphincter relaxing, as I massaged it, slowly working itself open. I penetrated myself and lathered my anal canal with the juicy mixture just like I had done many time before. After a few minutes, I could tell I was well prepared, I washed up and went back to the bed.
I slid my grandmother’s panties up my legs and over my hips. These were high waisted too and full bottomed, but the edges of the bottoms were loose frills instead of straight elastic. I then put on her silk nightie, which terminated mid thigh. It too was fairly plain and conservative, but it had string top shoulders and a strong taper at the waist, which accentuated my bust, and the material felt delicious against my skin. I wrapped myself in her thin cotton robe and tossed her jewelry on the bed. I applied a little extra perfume to my neck, and I hurried back to the bathroom.
I found my grandfather already brushing his teeth in the buff before having even toweled off. “Oh papi. Let me help you with that,” I said, as I surprised him. I toweled him off quickly and helped get him into his boxers, as he insisted. I grabbed his hand, “Ready to go to bed,” I asked, as I guided him out of the bathroom? I got a surprising pinch of my butt, as we walked out. He must have been feeling frisky. It was dark, but still early. I figured the lead up and wine helped get him in the mood. When we got in the room he pointed to his shirt, but I told him it was a warm night, so he should sleep without it. I pulled back the covers and put him in the bed, and he covered himself up.
My heart was racing at this point, as I stood at the door. I questioned whether I was going to actually go through with it, but my erection was killing me, my teen horniness was surging, and I wanted it bad. I slowly shut the door and turned off the lights. I walked to the bed and whispered, “I’m coming to bed too.” The moonlight was illuminating my silhouette, as I took off my robe, dropping it to my ankles.
“Ohh my,” my grandfather said, as the light traced my hourglass figure up to the tips of my fake nipples. My breasts jiggled beneath the thin material, as I pulled back the cover and worked myself into bed.
My heart was pounding out of my chest, and I couldn’t close my mouth because the excitement and anticipation was taking my breath away. I turned away from him, as I situated myself beneath the covers and projected my ass into his direction. I waited. I didn’t have to wait long. He must have been horny too because he worked faster than I had imagined. He moved his hand between the small of my waist up to my breasts and pulled my small body into his pelvis, so he could grind his cock against my ass. Not long after, he had yanked down my panties below my ass and had a grip of my breast under my nightgown, as his hard cock was eagerly thrusting between my cheeks trying to find someplace wet and hot. His cock was torpedoing out of his sheath that was pinned between my cheeks, jutting the head against my juicy, wet sphincter. I could feel the head hitting its mark, loosening up the muscles, as they acclimated to my grandfather’s appendage. He pulled me tighter to his hips, and his next thrust penetrated my insides before coming right back out. He did it again, but this time he didn’t retreat as far, and my sphincter had a moment to grip his cock.
A whimpering moan left my lips, as his cock worked itself back and forth in my virgin ass. He seemed to be finding the right position and angles to bury more and more of his cock in me. “Gentle papi,” I moaned, as he thrusted with gusto, gripping me with a death grip that surprised me; he had strength and energy I wasn’t expecting. He pulled on my twink body tight to him, and I could feel the perspiration building between us.
Then I felt him roll on top of me, and for a moment, it was hard to breath with my face pressed into the pillow. I felt the full weight of him on top of me, as his cock slowly pressed down into my prostate. I could feel my cock twitch, as he milked some fluids from the tip of my cock. He only stayed like that for a few minutes, with his hot breath next to my cheek, occasionally kissing it, before he picked himself up and straddled my ass. I could feel him pull up my gown, exposing my ass. Then I felt him grip my hips at the top of my cheeks and pull it into his cock, as he quickly worked himself back and forth. The perspiration on our bodies made him effortless slide on my thighs, as he penetrated my insides.
Having a cock in my ass felt amazing. The appendage was made for my hole. The rippling muscles of my anal canal sliding over the velvet skin of his shaft was sending me into a horny rage. I gripped the bed and pushed back against his thrusts. My toes were curling and my legs were twisting, as I was dying from painful pleasure. Maybe he could tell my eagerness, or maybe he was just ready to pound me and unload in me because he worked himself off of me, and I instinctively pulled my knees under my hips and spread my legs. He found a position between my legs, and then I felt the head of his cock press against my stretched sphincter. I instinctively came up on my hands to get into the right position, and then I felt his cock slide up into my body once more. He gripped my hips tight and began pounding my ass hard. My hanging tits were tossing about, so much so, that I was sure they would fly off. He was pounding his hips into my ass that there was a smack, smack, smack. I dropped to m forearms and face, burying it in the pillow, as I road out this ride. My cock was dancing in the air, getting a jolting wiggle with each impact that was sending me over the edge.
I had never came before by just anal stimulation, or maybe I just started masturbating before anything could happen, but I could feel the tip of my cock tingling on the edge of an anal orgasm. The silk nightie was teasingly caressing the length of my shaft, willing me to cum. Feeling it wanting to explode from me, I pressed back into his cock, and then it happened. I began to moan into the pillow, as I felt my cock and anus contracting in rhythmic pulses. Thin streams of cum shot onto the nightie and on the bed, as my sphincter gripped my grandfather’s cock. He must have felt it too because he collapsed on my back, and we fell to the bed, still joined. He had his legs still hooked inside my spread legs, as he never stopped thrusting into my ass. My bare ass was firmly pressed against his pelvis, and he was grinding down hard. My orgasm was over, but he was still using my ass, as I just laid there with exhaustion, just trying to breathe. With his breath close to mine, I could hear the tone of his grunts change, and his hips buck with less control, as I then felt his cock twitching inside me. He pushed down hard and held, as I felt his cock buck and pulsate in my ass. The feeling was amazing, as my stretched sphincter gripped his pulsating cock unloading his cum deep in my rectum. I was crushed, but I was in heaven.
After the last twitch of his cock stopped, he immediately rolled off of me, tearing his cock out of my ass. I could feel his cum running out of my gapping hole down my taint and balls. “Mmmm papi,” I said in euphoria. “That was good. You did me really good.” He was still catching his breath, I think more surprised than I was at the work he just accomplished. I felt used, but in a good way.
I moved over to his side and put my hand on his chest and my bare leg over his hips, nudging his slippery sex with thigh. “Mi amor. Mi Lucietta,” he said affectionately.
I leaned over to him and give him a kiss on the lips. “Thank you papi. Now let’s get you cleaned up.” I cleaned him up and put him back to bed. I didn’t stay; I had to clean myself up and put away the clothes. Plus, I couldn’t have my mother find me in bed with grandpa, so I headed to bed.
My grandfather was with us for a few more years before he left us, but in those years, we had a lot of fun, and I think we both brought each other a lot of happiness. He also helped me to find my place, as I am now fully transitioned and loving my place, as a nurse, and as a wife of an amazing man, who I eagerly service whenever he wants to take me.
The End