The High School Reunion

Story Info
Joel reminisces about his first time with Christy.
2.9k words
4.31
15.9k
25
Story does not have any tags

Part 1 of the 2 part series

Updated 06/11/2023
Created 01/06/2022
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

I was really looking forward to my twentieth high school reunion--for reasons I could never tell my wife.

I'm Joel Mathers. I'd been married to my wife, Miriam, for close to fifteen years; but what started as a loving relationship had deteriorated over the years to silly bickering and--to our own amazement and dismay--a slow but inexorable withering way of the affection we'd once had for each other. It was as if we were tumbling down some steep hill and couldn't do anything to prevent our inevitable crash at the bottom. We both knew our marriage was functionally dead, but neither of us had the gumption to actually make a break. You get that way sometimes: inertia just takes over, and you worry that being alone is even worse than being in a rotten relationship.

I made a token effort to invite Miriam to come with me to the reunion. To my relief, she declined.

"Are you kidding me, Joel?" she said in a harsh tone that matched the harshness of her expression. "All you guys reminiscing about good old high school days, leaving me totally out of the discussion! Are you forgetting that you didn't meet me until you'd graduated from college?"

"Of course not," I said. I would have added "dear" to the end of that sentence, but somehow I couldn't get the word out--it stuck in my throat. "I just thought you might like to meet my buddies from that time."

"No thanks," she snapped back. "The guys are probably fat and like to guzzle beer. As for the women--well, at thirty-eight some of them might still be pretty, and you're welcome to bed down with any of them if you should so choose."

"Miriam," I tried to say as calmly as I could, "I'd never do that."

"Wouldn't you? I beg to differ."

Let me be blunt: each of us had cheated on the other, multiple times. I think it was a kind of desperation. Sex isn't equal to love, but at times the physical intimacy of sex can seem like an acceptable substitute for love. I had a feeling she was wanting to stay home just so she could invite her latest lover over to the house to spend a long weekend with him.

Well, she was free to do that. For my part, I guess I was secretly hoping that I'd meet Christy again.

The funny thing was that Christy and I hadn't actually done anything in high school. We were friends, but that's about all. In fact, I don't think she had any boyfriends at all in high school. So she was just about the last person I expected to see on my doorstep that time in late August, just before we were about to head off to different colleges.

Our birthdays were within a week of each other, and both of us were now eighteen. Full-fledged adults! I think we were both looking forward to the freedom from parental supervision that would come in just a few days. But even so, I never expected her to say what she did as I opened the door in answer to her knock.

"I'd like you to take my virginity," she said in a high, musical tone that seemed to me the essence of femininity.

I gaped at her as I looked her over. She wasn't the loveliest girl in our class--but she was pretty close! Soft, flowing dark hair framing an oval face that was a strange mix of brightness and melancholy; lovely curves around the bust and the hips, with a really nice derrière (as I well knew from giving her admiring glances as she walked past me in the hallway of our school). A nice height, five foot six--not too short, not too tall. What better way to make a first venture into sexual union than to cuddle up with a girl like this?

Yes, I was a virgin too. I don't know if she knew that, but I think she sensed it.

I licked my lips and, after finally finding my voice, croaked out, "Okay."

I let her into the house. Did she know that my parents had gone off on some errand or other? Had she hidden somewhere and waited for them to get into their car and pull out of the driveway? This was one determined girl! She wanted to be deflowered, and she wanted me to do it.

I led her upstairs to my room. It was kind of a mess, what with my having to pack up whatever I wanted to take with me to college. But the bed--thankfully, it was a queen-size, easily big enough for two--was more or less made. I didn't want her to think I was a slob.

She looked around the room, nodded to herself, then turned to face me as I stood there like a dope. She gave me the most darling little smile you can imagine--tender but with a touch of alarm, even fear--stood up on her tiptoes (I'm a bit taller than her: five foot ten) and, placing her hands on my shoulders, gave me a soft little kiss on the mouth.

I barely had time to kiss back when she pulled away and then, turning her back to me, began to undress.

There is something about seeing a girl naked for the first time that really gets to a guy. All the mysteries of the female body suddenly seem to be revealed to your gaze, and you realize that the various parts are even more beautiful than you had imagined. But they're beautiful because it's the total picture--not just the individual bits--that makes it so. As Christy first took off her blouse, then shimmied out of her knee-length skirt, she revealed a back and bottom that looked sculpted by a master artist. In some crazy way I almost didn't want her to remove her bra and panties, because the mere fact of her exhibiting herself in her underwear was a touching moment that showed how much she cared for me and was making herself accessible to me.

Then she reached behind herself, took off her bra, and then, after only a moment's hesitation, stepped out of her panties.

If her backside was gorgeous, what she revealed when she slowly turned around was so incredible that I got dizzy and bleary-eyed.

Naturally, my glance focused on those parts that all men find mesmerizing, precisely because we don't have them. Her breasts weren't enormous, but they were the perfect size for her slender, willowy figure. They were surprisingly close together, creating a natural cleavage that I found exquisite. As I looked down her flat stomach to the rather thin patch of fur over her delta, I swallowed hard as I realized how close I was to that mesmerizing focus of every man's desire.

Christy smiled gently at me--because I hadn't done a single damn thing aside from just staring at this vision of female loveliness. She approached me and, with a strangely maternal bearing, began undressing me. All I had on was a T-shirt and jeans, and she pulled the one off of my head and unzipped the fly of the other and let it slip down to my feet. She expressed quiet approval of the big bulge in my underwear, and falling down to her knees she whipped them off my hips in a single motion.

The action was so fast that my erect cock almost hit her in the face as it was freed of its encumbrance. She laughed a little at that, but almost immediately stuck as much of my member into her mouth as she could. That was only about three or four inches--not bad for a virgin--and it was more than enough for me.

She seemed to have an instinctive knack for cocksucking: she alternately sucked hard on the shaft, rolled the tip around on her tongue, and used one hand to pump the base gently. I'm sure she didn't want me to come in her mouth, although it would have been easy to do that--and I was very close to exploding when she used her other hand to massage and knead my bottom. I could tell she liked the firm musculature there. Just about all women have a thing for a good male butt!

After a few minutes I had to stop her and lift her up to her feet. The desire to go into her was so overwhelming that I couldn't resist it any longer. I probably should have given some attention to her needs--and, in fact, as I led her to the bed and lay down next to her, I did check to see if she was wet. Of course she was. When I touched that magical spot, she actually winced and let out a little whimper. It's an incredible moment when someone else first strokes you down there. I also gave a lot of attention to her fabulous breasts. But I didn't waste time on these tedious preliminaries.

When I climbed onto her, as she spread her legs to accommodate my body, I looked down on a girl who was oh-so-ready to be penetrated, but still filled with a sort of delicious dread. I cursed Nature for designing the female body so that it almost always felt pain when experiencing this procedure for the first time. Man, what a bad set-up! But I knew, and she knew, there was no avoiding it.

So I plunged in.

I forged in almost to the hilt and shattered that poor little hymen in the process. Her face crumpled, and she let out a sharp cry; a single big tear got squeezed out of each eye. I felt rotten for hurting her--but that feeling was overwhelmed by the transcendent ecstasy of having my cock enfolded in a warm, tight, wet vagina. If there is anything akin to heaven on this earth, this must be it--for a man. I may even have shed a tear or two at the amazing sensation, as I lowered my whole body onto hers and buried my face in the crook of her neck. I don't think I've ever felt closer to another human being as I did at that moment. That's really the best part about sex--not just the physical sensation, but the sense of unity and connection that you can achieve only in that way.

I got into a good rhythm, and it seemed that Christy was getting over her pain and starting to enjoy herself. I tried to help her along by kissing her all over her face, and I also stroked her everywhere I could reach--breasts, back, thighs, bottom. I even reached down and placed my index and middle finger on either side of my cock as it was plowing into her: somehow I had to make absolutely certain I was actually in her, and that this wasn't some crazy dream I was having.

I had a feeling I couldn't hold out very long, and I didn't. Even though I felt a little mortified at being so quick on the trigger, I experienced an overwhelming emotion as I flooded her with my emission: that was the supreme way in which a man and a woman bond together. No matter what happens afterwards, they are fused by the glue of a man's come as it bathes the walls of a woman's vagina.

I pulled out quickly, knowing that Christy was still in a bit of discomfort. And I also snatched up some Kleenex from the nightstand and mopped up her pussy, which was already leaking a thick mixture of blood and semen. There wasn't all that much blood--but there was a lot of semen! I felt proud that I'd sent so much of my stuff into her.

We cuddled quite a bit afterward. She was grateful for that: she wanted to be reassured that she wasn't just a piece of meat that a guy had banged and then could just walk away from. But, not entirely unexpectedly, something happened to me as we snuggled there on my bed.

She looked up at me, a mixture of surprise, excitement, and a touch of apprehension in her face. "You, um, you're big again."

"Yes, I am. That's your doing, dear."

She smiled faintly at the compliment. "You want some more?"

"I'd like that very much."

"Joel, I'm pretty sore down there. I don't know if I can take another round."

I looked intently into her face. I didn't know how she would react to the suggestion I was planning to make, but I decided just to go for broke.

"We could try something else," I said.

She thought I was recommending some different position--but how would that help, if her pussy was still sore?

"What?" she said shyly.

I was lying on my back, Christy lying half on top of me. My hand was on her back, and it slid down to her bottom. My finger came close to touching her anus as I said, "I could go in here."

It took her a while to understand what I was saying. Then her eyes got big and her jaw dropped. "You wanna do that?" she said, almost in disbelief.

"Yes, I'd like to."

She gave a little pout. "My friends say that it hurts."

"It probably does hurt," I admitted. "But lube helps."

She mulled that over, biting her lower lip as if pondering some really difficult math problem. Then, all of a sudden, a broad smile covered her face as she said brightly, "Okay!"

I couldn't believe my luck. What we were going to do was pretty naughty, wasn't it? But I was so eager to get going that I pushed her aside, got up from the bed, and headed toward the bathroom. Fishing through the medicine cabinet, I chuckled as I picked up Mom's jar of cold cream. This should work!

Christy's eyes got even bigger as she saw what I had in my mind. She shook her head incredulously as she lay flat on her stomach, making herself ready to be lubed up. I admit that I felt just a tad queasy sticking my fingers into that orifice: I'd rarely placed my fingers into my own anus! But I managed it, then wiped my fingers with more Kleenex, and got on top of her.

She looked pathetically vulnerable, lying there in that prone position, her face buried in a pillow as if she wanted to avoid any possibility of seeing what was being done to her. It struck me that this position makes a girl feel even more submissive than the standard missionary-style vaginal sex: there's really not much she can do except take what a man dishes out, is there? As I inserted my cock into that place as gently and carefully as I could, I heard her let out a huge sigh as felt herself skewered anally for the first time.

Imagine a girl being deflowered twice in a matter of minutes! For this was as much a deflowering as the one she'd just been through. As for me--I was once again in heaven, for the extreme tightness of that aperture made it seem as if it was clinging to my cock and never wished to let go. The lube definitely helped me get going, and every so often I raised myself up to look down at myself: once again I wanted to see myself entering this heavenly creature in this unorthodox way, just to convince myself that it was actually happening.

This time I held out quite a bit longer. I also wrapped my arms around her chest and took her breasts in my hands, relishing their strange combination of firmness and softness. After a little while I slipped one hand down her front and cupped her sex. When she felt that, she turned her head to one side and her eyes popped open: I guess she was surprised that I was able to tend to her pleasure even as I was pounding her poor bottom with my member.

My second discharge seemed even more copious than my first, and I tightened my grip on both her breasts and her pussy as I emptied myself into her. I groaned right into her ear, and she let out a high-pitched squeal as she felt her orgasm coming on. Her whole body shook as that climax cascaded over her, and a few more tears got squeezed out of her eyes.

After it was over, I didn't want to pull out: it felt so nice and intimate being in her. But she let me know that she was feeling uncomfortable and that I should withdraw.

I did, and she got up shakily and went to the bathroom to clean up. When she came back, she seemed to want to avoid looking at my naked body as I lay flat on my back on the bed. My cock was streaked with cold cream and also with some of my own come, and she felt the need to take some Kleenex and clean me up.

"I'd better go," she said.

I nodded reluctantly, wishing she could stay with me forever but knowing that my parents might be coming back anytime. I watched her fixedly as she got dressed; I was content to remain naked. When she was fully clothed, she looked down somewhat disapprovingly at me, but bent down and gave me a little kiss on the mouth.

Then she walked out of the house. I never saw her again.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
1 Comments
AnonymousAnonymousover 2 years ago

Well, his wife is obviously fucking around on him, or she wouldn’t speak to him like she did, or give him her ‘permission’ to ‘bed down’ with as many of his old classmates as he wants. Feel sorry everyone in this story, actually. they all seem miserable and for good reason. Especially, when he realizes he’s been secretly gay for decades without knowing it, until he ends up ass-fucking some slut from his high school.

Share this Story

READ MORE OF THIS SERIES

Similar Stories

Comforting My Neighbor's Daughter I fuck my innocent neighbor when she comes to me for comfort.in Mature
Moms at the Beach Ch. 01 Newly single Moms make tempting targets for enamored sons.in Mature
A House Full of Women Ch. 01 45-year-old Jack gets it on with a college virgin.in First Time
Revenge of the Nerd: Bitch Sister Nerd uses formula to make his sister his submissive slut.in Mind Control
Bosom Buddies Ch. 01 A nerd befriends the 5 hottest girls in school.in First Time
More Stories