Grandma and I Ch. 03

Story Info
Gabby plans to lose her anal cherry to Gran on Prom Night.
9.9k words
4.75
22.7k
32

Part 3 of the 4 part series

Updated 06/11/2023
Created 02/06/2022
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
LL72
LL72
1,188 Followers

It was Prom and I was, to use a cliché, the Belle of the Ball. I had spent a week's allowance on having my hair done and another week's on my nails, though strictly speaking Grandma had subsidised both as an additional treat. The main treat, of course, was the dress -- a dark blue creation which went down to the floor, but with a cut that meant by sexy legs were continually being revealed for quick flashes as I walked, and with a low enough cut at the other end that whilst my large tits were in no danger of popping out, they were far from being fully covered.

Despite being asked by several guys I'd not accepted a date from any of them, instead hanging with my girl friends; even if many had their boyfriends with them I was seldom alone for more than a minute or two, as eighteen year old seniors, who had known each other all the way from elementary school, we stuck together. And to be fair, even if wasn't absolutely in, I wasn't totally out either and so when a guy came and asked for a dance I was happy to oblige as long as they knew that was all they were getting (a quick peek down my cleavage didn't really count as going any further, and as we were about to leave school for the last time it hardly mattered if the President of the Math Club got a bit more of an eyeful than he had when we were sitting in class). One or two tried to go a little further (not the Math Club guy who was a perfect gentleman and would probably die a virgin), but I easily slapped them down, my ass only gets groped when I want it to.

And I did want it to be played and kneaded, to feel firm fingers pressing into my round rump, digging into the flesh and squeezing it, before jiggling it up and down like a plaything. I took a sip of my non-alcoholic cocktail and subtly glanced round the room. There were plenty of teenagers, dancing and having fun, certainly a few of the girls, at another time, I could have been interested in, especially the soccer team's captain who managed to combine the hottest body in the school with a toothpaste ad smile and enough brains to get the top college of her choice. Clustering at the edges of the room like bats afraid of going onto the dance floor's light, were the teachers and volunteer chaperones, (as if without them we'd all be having a no-holds orgy in the assembly hall). I'm not going to deny that some of the female teachers had figured in my fantasies, and I'd certainly played with myself at night imaging Mrs Walker correcting my homework before rewarding me for my correct answers with a hard pussy licking over her desk.

But amongst the various volunteer chaperones, standing and having stilted conversations with the teachers they barely knew was someone who I wanted to grope my ass and more, my lover, my Grandma. She seemed to sense I was looking at her as she momentarily retreated from the group she was in to turn her head in my direction. She was far enough across the room and in the gloom away from the lights that I couldn't gaze into her eyes or even see much more than a pale pink face, expressionless and blurry. It didn't matter, it was enough that she was there and looking at me, and, I was sure, desiring me as I desired her.

My friend Shawna misread the look, which was lucky as she'd have freaked if she'd really known what I was thinking, "It's a bit of a pain your Grandma's here, I bet when your Mom had to bail you thought you'd have a wild evening."

"I'm a good girl," I said with a grin which suggested both Shawna and I might think I wasn't. Then cheekily, knowing that Shawna would misinterpret and think I was joking, "Anyway me and Gran will have a wild time later."

"What? A couple of glasses of milk and some cookies, before a kiss on the cheek and you heading to bed," Shawna laughed, little knowing how close she was getting, though the kiss would be a lot less chaste than she imagined and I wouldn't be in bed alone (I also wasn't sure about the milk and cookies).

I didn't correct her, and moved the conversation on. Even if she and the rest of my friends would never have guessed the real reason I kept glancing at my Gran they might instead think it was because I was bored or distracted with their company and that's not something a girl should do to her friends, so I moved back to the conversation, "I was just worried she'd be out of her element, it's not Gran's thing - anyway what's this about Becky and the college guy? Beck's spill..."

The conversation quickly moved away from Gran and onto my friend Becky's semi-drunken make out with a college guy the week before. However, whenever I could I quickly stole glances at Gran. She looked as sexy as fuck to my mind, rocking even a conservative trouser suit with a white blouse and I couldn't wait to get it off her as she got my dress off me. But that would need to wait. I continued to talk to my friends, agree to dances with guys who asked and sipped the non-alcoholic fruit cocktails which well meaning waiters kept placing in front of me.

I'm not saying I didn't enjoy myself, but it was definitely the enjoyment of Christmas Eve or the night before your birthday when you're eagerly anticipating the next day and no matter how much fun you're having with your friends, you know something better is about to come. I wasn't too disappointed when the lights came on and the Principal came up on stage to say a few words of wisdom before telling us to leave the building. I said goodbye to my friends, some of who were going onto a party, together with at least one who had booked a hotel room with her boyfriend where she was planning to lose her anal virginity. I'd made out I couldn't as we were having a family treat away and I needed to be up at the crack of dawn. It wasn't quite true, I was going to a hotel, but it was tonight and, I too was planning on losing my butt cherry to Gran that night -- which I guess technically meant it did count as a family treat.

I wasn't waiting long before Gran drove to the front of the school in her new 4x4. I lifted the hem of my dress and got in. Gran looked hungrily as I got in, "You look ravishing," she said. She had already told me that before we left my house, but I wasn't against being told again. Because we were still in school grounds and there were people around limited herself to kissing my cheek. She drew back. "I can't wait to fuck you," she murmured sexily.

"I can't wait for you to fuck me," I giggled, my pussy already starting to tingle at the thought of Grandma pounding me with her strap-on. "You're looking hot as well."

I had already said that as well. Gran smiled, "I had to dress formally for my girl's prom night. Speaking of which..." she reached into the glove box and pulled out the corsage she had bought me earlier, presenting it to me when she arrived at my house. I had worn it for the pictures Mom had taken of me in my Prom Dress, my Gran date beside me, hands round each other's waists, and then as she drove us to the Prom itself. On arrival I had taken it off, as we both agreed that wearing something that was traditionally bought for a girl by the person taking her, might raise a lot of questions which I'd have to lie about.

I slipped the corsage on, it felt as if the dancing in the middle had been an interlude and the real date was now just continuing. "How long until we get to the hotel?" I asked as Gran turned the key in the ignition.

"Just under an hour," Gran replied, "I guess we'll just have to practice the art of conversation."

I grinned, talking to Gran was easy, she was such a great talker, both entertaining in what she had to say and interested in my replies, always making sure the chat didn't drift into areas of which I'd no interest, like politics or business, whilst equally not sticking to the subjects I discussed all the time with my friends, elevating it above gossip and fashion. The hour flew by.

The hotel my friend had gone for to lose her anal virginity was the best that could be bought on a High School senior's budget. It had a double bed and a shower and TV (not that they'd be watching much) and was clean, which was all she wanted. Gran however wanted more, the hotel we were approaching was opulent, beaming brightly in the darkness as we approached it, with people still clustering on its terraces being served drinks by waiters in crisply clean black and white uniforms. We drove to the entrance and got out as a valet hurried down to greet us. Grandma explained she had already checked in our luggage earlier and handed him the keys to take the car to park.

The concierge respectfully opened the door, if he was surprised to see a teenage girl in a prom dress and a sixtysomething woman in a suit he made no sign of it. He gave a slight bow, "Welcome ladies," as we walked by him and I felt almost like a princess.

Grand, is the only way to describe the lobby. It was larger than most houses and taller as well, the brightly lit chandeliers hanging from a roof which was at least three storeys high, with marble stairs snaking round the room leading up to the floors from which you could look down at the fountain in the centre of the lobby or gaze across at the pictures that lined and classical statues that sat in the alcoves. Taking me by the hand Grandma led me over to the reception desk, even it was opulent, a marble top polished to perfection with a perfectly tailored middle-aged woman with an impeccable hair-do and nails so manicured they rivalled mine. "Room sixty nine," Grandma announced and as she was handed the key I had to keep myself from smiling at the number.

"I hope you enjoy your stay," the receptionist smiled automatically, "If you need anything please do not hesitate to call room service."

Grandma nodded as if this was all as she expected and led me to the lift. There was another, more conventionally aged, couple already in and we all remained silent until they got off at the fourth floor. Then as the doors closed, Grandma smiled and kissed me, her lips lingering for the length of time it took us to travel the remaining two floors. There was a ding as the doors opened and Gran broke from me, taking my hand instead and leading me down the corridor, it felt like the perfect Prom date.

She unlocked the door and I followed her in. It was bigger than any hotel room I'd ever seen, the bed alone was at least King Size, may be even bigger if that was possible, with silky satin sheets and mahogany posts which made it look like something from the colonial period, even if it was probably a more modern replica. There was a couple of very comfy looking sofas and a wardrobe which looked as expensive as the bed. Beside the balcony door was a table and a couple of chairs, perfect for sitting in as you ate breakfast with the doors open to let in the air and admire the view. Another door led to the bathroom and I walked in, my heels tapping against the marble tiled floor. There was a round bath-tub built into the floor, which was easily large enough for two.

"What do you think?" Grandma stood behind me, her hands gently resting on my hips.

"It's so big and luxurious," I said, "I could get used to it."

"I hope you do," replied Grandma and turned me around for another kiss, to which I eagerly responded.

After a few moments we broke and she led me back into the bedroom, leaving me standing as she walked over to what I thought was a cabinet in a sideboard but which actually contained a concealed chiller. She brought out of it a bottle in a metal ice bucket, "I thought some champagne as a treat," she smiled. "Could you find some flutes," she then added as I nodded eagerly. I quickly found them in another compartment of the cabinet as Grandma moved over to the table by the balcony. There was a pop as I approached and a small fizz of champagne trickled from the bottle's neck. She quickly poured the champagne into the glasses in my hand, before placing the bottle in the ice-bucket on the table.

Taking a glass she toasted me, "To you Gabby, the sexiest thing around."

I giggled, "Apart from you Gran, you're pretty fucking sexy as well." She smiled and sipped her drink and I quickly followed her example before deciding that I should toast her properly, "To Grandma, the hottest older woman a teen could want."

We sat down opposite each other, her hand reaching out to stroke the back of mine. Outside it was near black, with a small glow in the distance from a nearby small town and a few isolated twinkles from farmhouses or solitary cars. Over them all there was just a hint of the moon's crescent. I sipped my drink slowly as myself and Grandma talked about the evening and my school career and what I might do next. The champagne was cold and bubbly and sweeter than the ones I'd had before. Gran kept topping us up, just enough that I felt light-headed, but nowhere near drunk, Mom's tactic of allowing me to drink when I was younger paying off. Grandma refilled the glasses, "Shall we share a bath before bed?" she said with a smile.

I nodded, "That'd be fun."

She got up, "Let me start running it," she said and left for a moment to go into the bathroom. When she returned she quickly finished her drink and I did the same.

"You look beautiful," she said as I stood and I blushed happily, as she began to undo her blouse. As she did so I slipped off my corsage and carefully put it on the table, I'd take it home and keep it on my beside cabinet as long as I could before it wilted, a reminder of tonight and how special my Gran was. Her blouse was off and she was unhooking her bra. I don't where I get my large breasts from, but it's not from my Gran's side, as her pair were small and pert, almost more like a still growing teenager's. She dropped the bra on the chair, "Shall I unzip you?" she purred as I looked at her lovely, even if small, tits and tried not to salivate.

"Yes please," I replied, tossing my hair over my shoulder even though the dress was low enough my hair hardly reached the top.

She moved behind me and slowly unzipped me. I wiggled as she pulled it down, over my tits and past my hips, letting it fall to my ankles. A bra would have spoiled the line so my bosom was now free and out, Gran reached round and took the large pair in her hands, kneading them sensually between her long fingers as she moved her lips to the back of my throat to kiss and suckle the smooth flesh. "Mmnnn," I moaned happily, as I leant back against her, "Oh that feel's nice."

She carried on for a moment, before stepping away. I bent down and picked up my dress, carefully laying it on the couch, before I turned. Gran had removed her shoes and was now fiddling with buttons of her pants, I watched as she undid them, pulling them down to expose her silk panties. The underwear was only on display for a moment, before that too was gone showing me her sexy shaven slot that I had buried my face in so many times over the last month. She smiled sexily as she, in turn, watched as I put my foot on the chair so I could unclip my garter belt and then roll my stocking down, repeating it with the next one. The garter belt swiftly followed, then my new panties (bought by Grandma when she had got the Prom dress, so I was sure she appreciated them). I put my hand on my hip and posed sensually for her, "Bath?"

"Yes, in a second," she said giving me a long look. She walked over to the table and picked up the bottle, only a third left, but that was enough for her to refill both glasses, handing me one and taking the other. Still holding them we walked into the bathroom.

The timing was just right as the bath was nearly filled, not that it was easy to see the water level with all the bubbles Gran had put in, like it was a child's water adventure. She went in first and I followed her. She sat down in the curve and I sat next to her. She waited until I was comfortable before raising her glass again, "To a wonderful night."

"I'll drink to that," I grinned back before raising the glass and sipping the champagne within. Gran's lips moved closer to mine and I replied to the invitation, pressing forward and opening my mouth as I connected with her. Still holding the glasses in one hand we kissed passionately, our lips agape as our tongues probed and pressed at the other's, the wet saliva on them making them slip and slide as they grappled like two oiled snakes in a sack. Our spare hands were reaching round the other's back, hugging each other so we could come closer. Slowly my bottom moved along the seat, until I was pressed firmly thigh to thigh with Gran. I could feel every move she was making, her bare flesh rubbing sensually at mine and if it hadn't been for the bath I'd have been leaking like a worn hosepipe. Her hand played at my back, washing and massaging it, sending bubbles popping over my shoulders as the warm water rippled against us.

Gran pulled her head back and drained the champagne, putting the glass on the side before resuming her impassioned kisses. Her spare hand was now on my front, slowly tracing a line from the bottom of my throat, down into the bubbles and then water, before slipping between my cleavage. I put my still half-filled glass away, to drink it I'd have had to break the kissing and whilst the champagne was nice, it wasn't that nice. My own hand moved to Gran's thigh, squeezing it under the water. Her mouth moved quicker and harder, her tongue darting over mine like it was trying to strangle it.

I gave an excited groan as she began to fondle my tits, squeezing them sexually and pressing them together, so they squished up under hands. Her fingers slipped over my nipples, first one and then other, teasing them with her tips, before, as they went hard, nipping them between two fingers and squashing them and making them stand out even more. I kissed Grandma more heatedly, only breaking from it to take quick hurried gasps of air before planting my mouth back on hers and grappling tongue to tongue. Her hand went from my breasts, tracing downwards and I moved mine up her thigh, her legs coming apart as I reached the treasure between them and began to stroke.

"Mmmnn," Grandma was the one who moaned this time. Her eyes fluttered as my fingers moved up and down her crack, teasing the slot and finding the clitoris to push against. Then she grinned and was back at my mouth, her lips moving on mine. Her hand had paused on my stomach, the palm swivelling around in circles over my belly button. As I carried on playing with Gran's clit, she moved her own hand lower, her fingers finding my smooth slit and sliding gently between the lips. I shuddered in pleasure as she entered me, groaning and shuddering in the bath so the water rippled around me, the bubbles popping and reforming as the waves rocked beneath them. Gran also gave another moan, "I can't wait to fuck this pussy properly."

I decided it was time to let her know my plan. I slowly broke the kiss, leaning back so I could talk, "Not tonight," I said, "Not for fucking my pussy."

Grandma looked confused, "No? What do you mean?"

I gave a small giggle at her expression before putting on a more serious expression and reaching up to stroke her cheek lovingly, "I wasn't a virgin when we first had sex."

"I know," Grandma was frowning quizzically obviously not yet realising where this conversation was going, "It doesn't matter, you're eighteen, I wasn't expecting you to be, it's not the fifties."

I grinned wider, "Even so the first time should mean something and I'm still a virgin somewhere else."

Gran's expression changed from puzzlement to astonishment and then quickly to joy as she realised what I was talking about, "You mean...?" she said, not putting it into words in case she was wrong.

I bit my lip coquettishly before giving her a shy smile, "I want you to take my anal virginity."

"Are you sure?" Grandma asked.

I nodded, "As sure as anything, I want it be sometime special, with someone special and this, with you, is perfect." I paused, before adding, "That is if you want to?"

LL72
LL72
1,188 Followers