Stephanie and Willard Browne

by

Caution: This Romantic Sex Story contains strong sexual content, including Cheating, Cuckold, Humiliation, Size, .

Desc: Romantic Sex Story: She probably loves the guy, but she has issues the like of which are truly disconcerting.

The Hamilton High late December homecoming game and dance, and the related after event parties, was always the big event of the upcoming 1new year, every year, kind of a pre-prom I guess one might say. I was taking Stephanie Ward, my girlfriend of the past year. We were both seniors and were even talking about getting engaged and hitched after high school. The plan was for us to get engaged, me join the army and learn a trade, and for her to go to nursing school. And, upon my return, we'd get married. That was the plan; it was the plan no longer.

"Yes, Darla, he's taking me. It'll be boring, but it's better than nothing; not much better, but better," I heard her say. Darla Willis was Steph's best friend.

"Question Steph, if you think he's such a loser why do you stay with him. You could find a better class of guy if you wanted to?" said Darla. I heard my soon to be ex-girlfriend snicker.

"Take a closer look girlfriend, I'm overweight, My brown hair is always frowsy looking, I'm too damn tall, and my personality isn't the most engaging if you get my drift. What decent looking guy is going to want to have me around? I might be able to snare one of the nerds are us crowd; they're desperate to a man, but even Willard is better than them. No, I'm stuck with the guy, no doubt about it.," she said.

"All of the things you just downed yourself for are fixable—all of them—Steph, except being tall; and I see that as an advantage not a drawback. Willard on the other hand is not fixable. He's short, at best a C student, utterly without talent as a boy animal, and possessed of personality roughly analogous to watching the fishing channel. You really need to boost your standards, girl, really," said Darla. Stephanie did not catch the slight and very strange look in her girlfriend's eyes.

I heard my soon to be ex sigh. "Yeah, I guess," she said. "But it's too late to start the campaign now. Homecoming is this weekend."

I was stunned. Now I wondered why she'd agreed to be my woman, why she was making plans to marry me. Of course, having heard what I'd just heard, the answer was simple enough I supposed: she was of the opinion that she had to settle for me. Clearly her friend Darla was getting her to rethink her decision. I planned to second Darla.

I coughed to gain their attention. "Hi Darla, how's it going? Never mind Homecoming, Steph, I wouldn't want you to be seen with a short, romantically untalented, less than interesting, C student. You need to do what Darla is suggesting and raise your standards. Have a nice day, both of you," I said. Now it was the two of them that were stunned. I turned and walked off.

"Shit!" I heard her say to my back. "Will, stop. We need to talk. You can't just dump me four days before Homecoming." She was saying all of this as she tried to keep up with me. I wasn't running, but I was walking fast. I stopped and turned to her.

"After what you just said about me to Darla! A girl by the way who will spread it all over the school before lunch is over? I mean you expect me to take you to Homecoming after all of that!" I said. She sighed; she seemed to be doing a lot of that.

"Yes. You have to. I've spent; well, my dad's spent, a ton of money on my dress, I've got appointments at the hairdressers and the manicurist; you can't just dump on me and run off with your tail between your legs because I hurt your feelings! You have an obligation," she said. I couldn't believe her gall or her reasoning. But, at the same time I was intrigued.

I noticed we were standing in front of the girls' bathroom: how fucking appropriate, I thought. "An obligation? When you clearly hold me in contempt? How do you figure I have an obligation?" I said.

"Okay, I was out of line, saying those things to Darla. I apologize, okay. And, I will make sure she doesn't repeat what all I said. Yes, I know I dented your ego, and I'm sorry for that. But, frankly Willard, you are too short and you are boring and you are not all that bright; but, all that said, I'm no prize either. We need each other. You have to take me to Homecoming. I'd just die if you humiliated me like that, Will. Please, dump me afterwards if you still want to, but you have to take me," she said. I stared at her. I stood there switching my weight from one foot to the other. I stopped.

"Okay, I'll take you. But don't expect a lot of enthusiasm on my part. You hurt me pretty good with all you said. As for after Saturday, you can consider us history. You can start hunting for my replacement after that. Got it?" I said. She nodded.

"I'll make it worth your while," she said. "No more put downs, I promise. Just take me and be polite. Okay?"

"Yeah right," I said. I had acquiesced at least partly because my dad had also spent a ton of money. I had a new suit, a forty dollar corsage already paid for, and a limo also already paid for. By honoring my "obligation" I'd at least get the use out of them, and who knew, maybe I'd find me a new woman; I'd sure as hell be scouting the floor for one. I was not the loser she and her friend Darla apparently thought me.

Yes, I was short at five-five. Yes, I was an inexperienced lover, but I'd could learn. And, I was most definitely not a fucking C student, not really; I got C's and B's that was true, but I could have gotten A's, just not while working the thirty hours plus a week, every week, all nights and weekends, that I did. Why work so hard? I had been saving up for our wedding, mine and Stephanie's. My family was not actually rot gut poor, but rich we definitely were not: lower middle class pretty much described us.


Homecoming was being held in our school gym. It wasn't crowded yet. Steph and I were not the first ones there but we were early. We meandered our way over to the already set up refreshment table. I ladled out a plastic glass of punch for her. She took a sip as I was ladling out one for myself.

"Jesus, Will, somebody's already spiked this stuff," she said. "Rum, I think."

"I tried it. You're right," I said. "And it is Rum. I'm bettin' one-fifty-one."

"This is going to be one hell of a party, boyfriend," she said.

"Boyfriend?" I repeated.

"Your ego still in the shitter from what I said the other day?" she said.

"Yeah, right along with my heart, girlfriend," I said.

"Will, I am really sorry for my stupid remarks. My head had to be a yard up my ass for sure. Forgive me?" she said. I stared at her for a long moment.

"What the hell. Okay, but no more of that stuff. Okay?" I said. Okay, I was hard up; so shoot me.

"You got it," she said.

People began arriving. The professional DJ hired for the evening got things started. Soon the gym was filled with laughing and clowning students doin' the boogie and generally getting down.

Steph and I danced the first three numbers, one of which was slow. She gave me the high sign and I headed for refills at the punch bowl. Yeah we knew what was what, and we figured so what.

Then something happened that surprised me, and I think Stephanie more than me: different boys began asking her to dance. She did look good from my perspective; she'd outdone herself at the beauty parlor. But, nobody had ever cut my time with her before, but now they were—they meaning plural. Before the night was over I'd gotten but one more dance with her; and, spent less than twenty minutes with her total socializing when we—she—wasn't dancing.

I should note that I did get two dances myself apart from my four with Steph. Both of those were with Darla Willis, go figure. It might be useful to note something about Darla here. Darla was a cheerleader with a cheerleader's body and ponytail and C-cup breasts and bubble butt and bubbly personality and parents with money; put another way, utterly out of my league. So why did 'she' ask me to dance? I had my suspicions, but she did, and I did—dance with her that is.

Then the night was over, and something happened that frosted me pretty good. Stephanie came up to me, looking kinda sheepish, and asked if it would be all right for Sammy Gilchrist, El Jocko Mangusto Supremo, to take her home. "I know you're probably disappointed, Will, if you say no I'll just tell him I'm going home with you. But..."

It was surreal. After all her efforts to make up with me. After my reprogramming my head to forget about all she'd said about me to Darla that day. After all of my planning to get with her after the dance and surrender my cherry to her; she wanted to go home with Sammy Gilchrist. Well fuck! I gave her my you've got to be shittin' me look.

"Whatever, Stephanie, go ahead. Go, make his day, I mean night," I said. She gave me a look, touched my cheek, and strode off to join her new boyfriend.


The following Monday she plopped down across from me in the cafeteria. "Hi Will, we got a party to go to Saturday night at Andrea's; I just got the word. It's her birthday," she said. I looked at her, stood, picked up my platter, and walked off. I think she was actually surprised. I was dumping my trash when she caught up behind me.

"Will? Is something wrong?" she said. I couldn't believe her. I actually thought it was funny. I laughed, causing any number of other folks to stare at us. I didn't answer her; I just walked off leaving her there. But that wasn't the end of it, oh no, that would have been too much to ask.

I was in the caf early the following morning when she plopped down across from me much as Stephanie had the day before. She looked good; well, she always did.

"Good morning, Darla. You're up early too, I see."

"Yes, I need to do a little prepping for a quiz in Michelson's class," she said. I nodded and went back to nibbling on my bran muffin.

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Story tagged with:
Cheating / Cuckold / Humiliation / Size /