Kelly's Diary 145 - High School Regrets - Cover

Kelly's Diary 145 - High School Regrets

Copyright© 2025 by Kelly85

Chapter 2: Nancy Puts Her Plan Into Action

Erotica Sex Story: Chapter 2: Nancy Puts Her Plan Into Action - If you're like me, it's probably more the things you DIDN'T do in high school that you regret more than anything you did. Even then, it's not really WHAT I didn't do so much as WHO I didn't do. Although we can't go back in time and do things over, sometimes you get another chance at it later in life. The question was, what would I do when such an opportunity arose?

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Fa/Fa   Oral Sex  

After high school I went to college out of state and other than during summer and various holiday breaks, I didn’t see much of the hometown so I had no idea what happened to either guy. With time, memories fade and I hadn’t really even thought about either of them in ages until I played Truth or Dare with my friends and Nancy mentioned that one of her secrets in high school had been the desire to fuck Todd. You can imagine the shocked look on my face we I learned we both had wanted the same nerd to fuck us. Life can be so funny at times.

After our “Truth or Dare” get-together, the next time I had lunch with Nancy we discussed her answer about Todd. Of course, neither us had wanted him as a boyfriend and would’ve dropped him like a hot rock after the first time, but each of us felt the same way - that he was the “fish” we both had let get away. Guys aren’t the only ones that occasionally look to add a notch in their belt.

A couple a days later Nancy called me and asked if I wanted to go out the following Friday night with her to see a movie. There were several new ones out we hadn’t seen yet and since I had nothing planned I figured why not and accepted. Nancy was the quietest in our infamous little foursome that dated back to when we were all in preschool. As one of her closest friends, I knew that “innocent and naive” Nancy could get just as horny and naughty as the rest of us, she just didn’t express it publicly to the degree the rest of us did. She was always more the follower than the leader, willing to go along with about anything but hardly ever initiating anything herself.

Friday night came along before I knew it and I got myself ready to go. I figured we would go to the movie and then probably grab something to eat afterwards, maybe at a local Eat ‘N Park restaurant or TGI Friday. It was just going to be the two of us and while we may have gotten a bit carried away the previous week at my house, I had no expectations whatsoever that anything would happen like that again between just the two of us. We were good friends and I enjoyed being with her, trading stories and gossip. When I went out with my cousin Kristen or best friend Beth, I never knew what was going to happen; but with Nancy, it was a pretty safe bet we would have a pleasant, rather uneventful evening out.

With that in mind, I decided to stick with a simple pair of tight, low cut jeans and my favorite pink tank top. Even if I was with Nancy, I was STILL out in public so why not look good? You never know, maybe some hot guy would walk by while we were having dessert! The tank top was a bit too small for me but I liked the way it clung to me as if it was painted on. Without a bra, my nipples poked through as if nothing was there and you could even make out the full outline of the entire areola.

Nancy had volunteered to drive so I waited on the couch in the living room, watching out the picture window. It wasn’t long before I heard a car approaching, the noisy brick street in front of our house amplifying the sound of the tires. Soon her little red Saturn appeared and pulled up to the curb. Nancy didn’t bother to get out of the car but instead just beeped her horn quickly a couple of times to let me know she was there. Since my parents were out for the night, I turned off the lights, grabbed my purse, and locked the front door behind me. I jumped in the front seat and Nancy immediately took off almost before I had the door closed, not even bothering to say hello. She seemed to be nervous but at the same time she had this mischievous smile on her face she always got whenever she was trying to hide something, a habit which just made her attempt at deception all the more obvious.

“Well, hello to you too girl!” I huffed, struggling to put on my seatbelt as she took the turn onto the main road so sharp that I was thrown against the door, “Ummmmm, is there something I should know about?”

“You could say that,” she replied with an air of mystery. It wasn’t like Nancy to be so mysterious so what was she up to anyway?

“And are you gonna tell me or what?” I asked growing a bit exasperated.

“Well, if you’d paid the least bit of attention when you got in the car, you would’ve noticed,” she fired back rather snarky.

Now what the heck was she talking about? The hair seemed to stand up on the back of my neck suddenly and I looked over my shoulder to the back seat. It was then that I noticed for the first time that we weren’t alone. Holy crap, there was a guy in the back seat! I turned to Nancy with my mouth wide open. What the heck? My expression couldn’t have been hard for her to read.

“What’s the matter Kelly, don’t tell me that you don’t know who that is!” she asked, her tone changing to one of triumph at putting this over me.

I looked back again where he was sitting with his hands on the seat next to him, a grin on his face but so far not saying a word. He looked to be tall and while not skinny, he wasn’t overweight by any means. He had thick blonde hair that he’d let grow over his ears, which seemed to stick out from his head a little more than necessary. One thing that immediately caught my eye was that he had the most piercing blue eyes. It was like they could shine in the dark they were so bright and when he looked at me, it was like he was seeing into my soul. He was dressed casually, jeans and a polo shirt. Overall, he was your typical decent looking guy you might find anywhere and walk by without noticing. Why she thought I would know him was beyond me.

“Oh come on Kelly, I can’t believe you don’t recognize him,” Nancy teased me, “Maybe I should’ve had him wear his lab coat with his hard cock poking out of it.”

The poor guy grimaced at that one, as if her last comment had caused him physical pain but he was a good sport and kept silent. Lab coat? Erection? What the heck was she talking about?

“God Almighty Kelly, you’re supposed to be the smart one but you can be so blind sometimes,” she sighed, “Really girl, don’t you remember who we talked about the other day ... the guy we both wished we’d done back in high school?”

No, it couldn’t be! Todd? Geeky and skinny little dork Todd? Where was the acne, the horrible black rimmed glasses, the ever-present pocket protector? No crew cut? How did he grow up so much since high school that I didn’t even recognize him?

“You’ve GOT to be kidding ... Todd?” I said to him, staring at him like he was the latest exhibit at the zoo.

“Yeah, it’s me and...,” he started to say, the grin broadening on his face but Nancy cut him off before he could finish.

“Well, after we talked the other day it hit me ... why not see if Todd was still around? So I called up some people who called some other people and it didn’t take long to find him. Did you know that he still lives around here, just on the North Side now?”

I looked back at Nancy, still unsure exactly what was going on. Had aliens abducted my friend and replaced her with this clone? The Nancy I’d known all these years would never have done such a thing.

“OK, like so I called him told him about what we talked about and then asked if he wanted to join us tonight,” she continued.

“You told him about THAT?” I asked, feeling a little funny inside now. This was getting to be WAY too weird for me.

“Hey Todd, why don’t you be a good sport and tell Kelly what I asked you about,” Nancy called back to Todd as she drove on. It was then I noticed we weren’t heading to the theater but instead we were going almost in exactly the OPPOSITE direction I would’ve expected.

Todd’s face reddened a bit as he seemed to be working up the courage to speak. Well, at least he still had some of the old shyness about him. “Nancy told me about your game last week and asked if I had wanted to do either of you back then.”

“And then what did you tell me?” Nancy pressed on.

“Well heck, EVERY guy in school wanted to do you two,” he said, swallowing hard, “It wasn’t just me.”

“And do you still want to?” Nancy pushed him more.

“I guess,” he stammered, “Are you really serious about this?”

Nancy slapped her hand onto my leg sharply and asked, “What do you say Kelly, are we serious?”

Sheesh, what COULD I say at that moment. Talk about your night’s plans taking a sudden detour. First off, I still couldn’t believe Nancy had done such a thing. Second, how had she convinced him to do this in the first place? Finally, I was still trying to get my head around the fact that this guy in the back seat was really the same dork I knew back in high school!

“OK, what’s going on Nancy?” I finally managed to get out. “Why is he here ... for real I mean?”

“Well, after we talked about him the other day I couldn’t get him out of my head so that’s why I tried to find him,” she explained, “I just figured we could go back to my place and get to know each other a little better, if you know what I mean. Sure beats a movie, don’t you think?”

Well, that all made sense based on the direction we were heading. At the speed she was driving, we would be at her house in a few minutes provided we didn’t get pulled over in the meantime by one of Pittsburgh’s finest. That didn’t leave a lot of time to say yeah or nay to the whole idea. Of course my first instinct was to say yes. After all, it wasn’t like he was still that stupid dork at school so why not take advantage of a golden opportunity to get laid? Besides, it had been a while since I’d been fucked so this was like a dream cum true! On the other hand, the whole thing seemed rather manipulative. What was REALLY happening? What was I missing here?

Before I could say anything more, Nancy pulled into a parking space in front of her apartment building. I’d been to her place several times, but it was always just to visit, never anything like what I thought she had in mind now. For that matter, Nancy and I had NEVER done anything together like what I starting to suspect she was plotting. Boy, you think you know someone like the back of your hand and then she pulls something like this on you!

We got out and quickly went up the wooden stairs to her apartment. Todd fell in behind and didn’t say a word but I had a feeling I knew where his eyes were focused as Nancy and I made our way up the stairs right in front of him - at least I knew where his eyes had BETTER be. Nancy unlocked the door and we both followed her inside. The first thing I noticed was the place was empty, even though I knew she shared it with another girl. What exactly Nancy’s relationship was with her was a subject of heated debate amongst the rest of her friends as she steadfastly refuse to even discuss it. Whether she was doing that to tease us or hide something I hadn’t quite figured out yet Nancy must have noticed me looking around for her.

“Yeah, Julie’s out with her guy tonight ... probably won’t see until tomorrow if I know her,” Nancy explained.

Was that supposed to be a hint that Julie wasn’t a lesbian or did it mean she was bi? Nancy didn’t bother to elaborate as she headed for the refrigerator and called back to us, “Beer anyone?”

I breathed a sigh of relief when Todd refused as I hate the taste of beer and even more so, what it does to the flavor of a guy’s cum. As much as I normally LOVE to eat as much cum as I can get, there’s an unpleasant aftertaste when the guy has been drinking too much beer that I’ve never cared for. Nancy knew better than to expect me to drink any so she wound up bringing out a few Diet Cokes.

“So tell me Todd, what do you think?” Nancy asked, a naughty grin on her face.

Todd looked bewildered, sort of like a little lost puppy. Apparently Nancy really hadn’t told him a lot and I was getting the impression her call to him had put him in an awkward position where he couldn’t refuse her request to meet us without seeming rude. I had a sneaky suspicion that until the past few minutes he really hadn’t believed that anything was going to actually happen and probably was prepared for it to turn out to be some kind of practical joke.

“Ummmmm ... what do you mean?” he said, his voice sounding a little strained as his eyes moved between the two of us girls.

“Oh Todd,” Nancy said seductively, shaking her head slowly, “You know what I mean. Kelly and me ... do you still want us? Let’s be honest ... do you want to fuck us?”

This was an interested side of Nancy, one I hadn’t seen before. To openly taunt and tease a guy wasn’t her usually M.O. and I wondered if she was doing it more for my benefit than his.

“Yeah right, like you’re REALLY serious,” he said, sounding a little annoyed now if anything, “I should’ve never gone along with this.”

He started looking around as if he was waiting for the cameras to emerge and someone to yell “surprise!” Well, there was one way to demonstrate our intent (well, at least what was already Nancy’s intent which was now becoming mine as well). If for me it was like some kind of dream and the reality of the situation hadn’t quite sunk in yet, I could only imagine what was going through poor Todd’s head! At times like this a person just responds automatically and with my past experiences, I was undoubtedly much better equipped to handle the situation than he was. But first I had a couple of issues to clear up that had been bugging me for years while I had the opportunity.

“So tell me Todd, were you masturbating when you peeked through the lab door window blinds at Robin and me in Chemistry class?” I asked. Of course we both had been convinced at the time that he did but there had never been an “official” confirmation.

“Ummmmm,” Todd looked decidedly embarrassed but managed to answer, “I guess so.”

“Ha, I KNEW it!” Nancy cried out, hearing the answer, “I TOLD you he was doing it. Robin always said so.”

“Hey, don’t blame me ... it was your fault,” he tried to explain, “I mean, wearing those short skirt outfits and showing off your legs and ass all the time. Damn, what did you EXPECT a guy to do?”

“Well ... we expected you to do exactly what you did,” I replied with a smile. “So if you did THAT, then why did you avoid me all the time whenever I tried to get close to you?”

“I don’t know,” he stammered, “I mean, look at your reputation back then. I figured you were just teasing me and having fun at my expense like the other girls did. I knew you never would’ve gone out with someone like me.”

I was starting to realize that while Todd had matured into a good looking guy, he was still a little on the insecure side. Well, I knew I could fix that!

“Do you know what I would’ve done if you had asked me out, Todd?” I asked in a low, seductive voice, deliberately licking my lips just enough for him to notice.

“Ahhhhhh, I’m not sure,” he said, hesitating before he answered.

“You said I had a reputation. So what do you think I would have done?”

Todd’s face was flushed now and I knew I was getting awfully close to crossing the line in terms of teasing him versus embarrassing him. I’m sure there were enough guys telling their friends about me that there was no doubt he knew exactly what I liked to do on a first date. Judging from the growing bulge in his pants, he was probably thinking about that reputation right now.

“Well then, since I didn’t get to show you back then, would you like me to show you now?” I asked with a wink towards Nancy who was grinning from ear to ear, obviously pleased with herself for setting up this little encounter.

Without waiting for Todd to respond, I stood up and quickly stepped up in front of him where he was seated on the center cushion of the couch. Reaching to my waist with my arms crossed, I grabbed my tank top with both hands and with one swift motion, lifted it up and over my head, dropping it to the couch beside him. For a few moments I just stood there in front of him, wearing just my jeans and shoes with my now bare breasts on full display for him.

“So what do you think, Todd, worth the wait?” I asked him as I cupped my boobs and bounced them a little in my hands. The way his jaw dropped and his eyes zeroed in on my boobs like a laser told me more than anything he might’ve said if he had found his voice. I loved the way it made me feel when guys like Todd stared at my body. It made me feel sexy and good about myself. Moving up closer to him, I leaned over him and put my hands on his shoulders so that my boobs hung down in front of his face. At barely a 34C, it wasn’t like they swung like pendulums or anything but he was getting a pretty good eyeful of what I had.

“You know, you CAN touch them if you want to,” I whispered softly to him, “They won’t mind.”

Todd hesitated and then reached out and gingerly put one hand on each of my boobs. At first he just planted his hands against them with his palms flat. Then his fingers slowly curled, just slightly at first and then more as he started to squeeze my boobs.

“Well, do they feel good?” I pressed him.

Todd just nodded and then squeezed them some more, letting my hard nipples poke out between his fingers as he did. I looked over at Nancy, who was watching our every move, and motioned with my head for her to join in. After all, it had been her idea to do all this in the first place so why should she be relegated to spectator status? Nancy took a deep breath and moved in besides me, dropping her blouse and bra along the way.

“Here Todd, why don’t you try Nancy’s now,” I said as she moved up tight against me. She felt so warm and soft and for a moment I recalled being with her not so long ago at my house with our friends, Her boobs were more like a 36D - or bigger and they hung down a lot more than mine but at the same time, it gave him a lot more to grab onto.

“Mmmmmmm,” Nancy purred as he massaged her hefty boobs, “Suck on them.”

For a moment I almost bent over to grab her boobs between my lips but then I realized she was talking to Todd. He dropped his head and took one of her nipples in his mouth and began to gently suck on it. As Todd seemed to be happy sucking on her larger boobs, I decided to stop messing around and get down to business.

I dropped to my knees on the carpeting in front of him where I pushed his legs apart and then reached in to unzip his jeans. His belt was a pain to undo but I figured it out and unbuttoned his jeans. Pulling the jeans apart in the middle, I reached in under the elastic band of his Jockey underwear (it would have been a lot easier if he’d worn boxers, or better yet, none at all) and finally found the head of his dick. Not surprisingly, he was already erect and I released his cock from the containment of his underwear and it popped out, evidently happy to have been freed from its cotton prison.

“You know Todd, I bet this is what you wanted me to do when you spied on Robin and me in Chemistry class,” I said as I grabbed his dick in my hand.

Todd took a couple of seconds away from sucking on Nancy’s incredible boobs to answer saying, “Oh my god, you have no idea how much.”

“So have you had a girl suck your dick yet, Todd?” I asked him, stroking his dick with my hand slowly. Based on my experience, I placed him at about six inches but he was nice and thick, more so than average for his size.

“I’ve had a couple of girls in college who did it,” he admitted before Nancy pulled his head back to her chest which shut him up.

I couldn’t help but feel a little disappointed. It would’ve been hot to give him his first BJ but then again, he WAS 23 and it was a bit much to expect any boy that age not to have had his dick sucked at least once. But still, you can’t blame me for wishing he hadn’t.

Keeping his mouth on Nancy’s nipple, Todd helped me pull his pants down and off his ass until they were gathered at his ankles. That was good enough for me, at least for the moment. I took a long look at his dick and wondered how many times had he masturbated and then squirted cum out of it dreaming of me doing what I was about to do now. Lowering my head to his crotch, I took just the top of his dick in my mouth and then let my tongue tease him, poking it into the tip of his dick and then running it around the smooth skin of his engorged cock head. As I breathed in deeply, I noticed that he smelled especially good, a little musky and sweaty but then it WAS hot outside and who could blame him for having a little body odor to him?

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