The Poor Girl

It looks like 14-year-old Gerald will not be asked to the upcoming Sadie Hawkins dance until Carolyn, the poorest girl at his school, asks him to be her date.

Part One

When I, Gerald Chester, was in middle school in the late 1970s, social events were prominent. There were the usual dances, but we also had games nights, amateur theatricals, casino night (real money was not used, of course) and numerous other fun events that the student council dreamed up. They were all well attended.

My mother often knew about some of these events before I did, because she thoroughly read the various school newsletters that I brought home. They always featured a calendar of upcoming events. Therefore, it was my mother who knew before I did that there was a Sadie Hawkins dance coming up in about two weeks. She mentioned it one night during dinner. I had to ask what that meant.

Mom explained, “A Sadie Hawkins dance is one where the girls ask the boys for a date—not the other way around.”

I joked, “Oh, good! Now I can reject the girls as often as they reject me.” I was only partially kidding. I was 14 years old and not exactly a girl magnet. A couple of times I had been turned down flat when I asked a girl in my class to go as my date to one of my school’s social events. Those rejections stung—so I basically stopped asking.

My comment did not go over well with mom. “Gerald,” she began in a sterner voice than usual, “if some girl asks you to this dance, say yes. Speaking from experience, it takes a lot of courage for a girl to do this. Girls have been conditioned to wait for boys to ask them for dates. You’ll hurt a girl’s feelings if you say no.”
“It’s funny how that doesn’t apply the other way around,” I noted. “No girl seemed to care very much about my feelings when she said no to me.”

Mom continued without conceding that I had a valid point. “Be that as it may,” she said, “the first girl who asks you to go with her to this dance—say yes. Do it for me, Gerald.” Mom always used that last sentence as a way to get me to do anything I wasn’t eager to do. It worked every time, too.

“Okay, I’ll do that for you, Mom,” I declared. “Maybe Susie Knight or Vicki Carter or Jessica Marble will ask me to the Sadie Hawkins dance,” I said. They were the three prettiest eighth-grade girls by far. Whoever was next in that queue was a distant fourth place.

My mom did not realize I was being sarcastic when she replied, “Sure, Gerald. You never know.”

“Yes, I do know, Mom!” I retorted, “That’s not going to happen. There’s a better chance of a blizzard striking Tahiti this week than any of those girls asking me to a dance or any other school activity. That’s an absolute certainty.”

Part Two

It must not have snowed in Tahiti because I got no date offers from the three top-tier girls over the next week and a half—nor any other girl for that matter. I had basically forgotten about the dance until it was mentioned during the morning school announcements by the principal on Wednesday. The dance was on Friday night. I already had made tentative plans to hang out with a few of my dateless male buddies that night doing something manly, like watching sports on television.

As I was putting my schoolbooks away and collecting my jacket from my locker, I was startled to see Carolyn Holmes standing near me. She had approached me from behind and tapped me on the left shoulder to get my attention.

Carolyn had been a classmate of mine since the second grade. I paid little attention to her normally. She was no better than average-looking (but so was I), with short-cut black hair that did not seem especially attractive. Moreover, she seemed like she was not a peer of mine despite being my age—14. Carolyn came from a household of very modest means. Her clothes always seemed to be well-worn and were almost certainly second-hand. She never seemed to buy anything the school was selling, from yearbooks to milk in the cafeteria. I think she self-segregated to avoid revealing that she came from a poor background. I could not recall ever having had a single conversation with Carolyn except when we were occasionally slotted into the same groups for school projects.

“Gerald,” she said to me, “it’s taken me a week to muster the courage to ask you this: If no one else has asked you ahead of me, will you be my date for the Sadie Hawkins dance on Friday night?”

That question came as a huge surprise. I had seldom seen Carolyn at any of the school’s social events. Then I had an epiphany: Most of those required nominal paid admissions. The Sadie Hawkins dance, to encourage attendance, was free of charge.

“No one has asked me yet,” I replied honestly. “Girls don’t generally have much to do with me.” I could visualize my mother urging me to agree for the sake of being nice to Carolyn, so I added, “Therefore, I guess I’m all yours on Friday.”

Carolyn beamed and gave me a quick, unexpected hug. She said, “I guess I’ll meet you here Friday night when the doors open for the dance.”

“Yeah, I guess so,” I agreed.

When I got home, I informed my mother that, to my amazement, I had been asked by a girl to attend the Sadie Hawkins dance on Friday and had accepted.

“Was it one of those three girls you mentioned to me a couple of weeks ago?” Mom asked optimistically.

“Yeah, right, Mom,” I said. “And the Chicago Cubs will win the World Series this year.” My mother didn’t follow sports at all, so she didn’t get the analogy. I told her, “No, it was Carolyn Holmes who did the asking.”

Mom sort of knew who Carolyn was due to her occasional volunteering at the school when we needed parents to accompany us on field trips. “Carolyn?” she asked. “Isn’t she the girl whose family doesn’t have a whole lot?”

“Yes, that’s Carolyn,” I confirmed.

“Well, that was very nice of you to have accepted her invitation, Gerald,” Mom stated.

When I reminded Mom that she had practically ordered me to accept the first invitation to the dance that I got from any girl, she asked me, “Are you saying you might have turned down Carolyn if I hadn’t pressured you to accept it?”

“Well, maybe,” I replied honestly. “I just don’t know. I accepted her invitation automatically because of what you instructed me to do about ten days ago.”

“Gerald, don’t you like Carolyn?” Mom asked.

I paused for a moment and said, “Mom, I basically don’t have an opinion about her. Up until today, I don’t think we’ve ever said two sentences to each other that weren’t related to schoolwork.”

Mom pressed the issue and continued with her questioning. “Is it because she comes from a poor family that you hadn’t interacted with her?”

“Maybe,” I admitted, “but It’s not that I deliberately shun her, Mom. Carolyn does a good job in segregating herself from everyone in the eighth grade—boys and girls alike.”

“Well, whatever the case, Gerald, I want you to be especially nice to Carolyn at the dance on Friday.”

“I knew you’d say that, Mom,” I replied. “You are quite predictable.”

Part Three

When Friday night arrived, I donned my best clothing and headed to the dance to meet Carolyn. She had arrived before I had and was waiting amongst the other students for the gym doors to be opened. We both spotted one another at about the same time. A relieved expression seemed to overtake Carolyn’s face. I think she had been afraid that I wouldn’t show up.

I was pleasantly surprised to notice Carolyn had dressed the best I had ever seen her. She was wearing a dark blue, short-sleeved dress with a design of moons and stars decorating it. It flattered her. I immediately complimented her on how she looked.

“Thank you, Gerald,” Carolyn said to me with a smile. “This is the best dress I own. I don’t think I’ve ever worn it to school. However, this is a special occasion.”

I thanked her for that veiled compliment. Then the doors opened and everyone swarmed inside the gym. Before the music began, Carolyn and I walked to a distant area that had benches where we could sit.

“I have to make a confession,” Carolyn told me. “I’m a lousy dancer. Even with this disco music, I don’t have a clue about how to dance. I’ve never attended a dance until tonight.”

I certainly had never seen Carolyn at a school dance before, so that news did not come totally as a surprise to me. Still, I felt a bit sorry for her, so I noted, “I’m not exactly Gene Kelly myself, and I don’t especially like disco dancing. I don’t like my dance partner to be five feet away from me. Let’s just wait until a slow song is played. All you have to do is just hold onto me and sway to the music.”

Carolyn grinned and said, “That’s more than fine with me, Gerald!” I got the idea that was exactly why she asked me to be her date at this dance.

After about three disco songs had been played by the deejay, something slow finally was played on the turntable. In the meantime, Carolyn kept on moving closer and closer to me on the bench we were sharing. She finally got enough nerve to embrace me. Being the gentlemanly type, I embraced her in return.

Things began to accelerate. Carolyn began planting kisses on my cheek, so I returned them to her cheek in equal numbers. It was a good thing we were well hidden from the volunteer parent chaperones because Carolyn became very liberal with her hands, placing her right one on a very delicate part of my anatomy and giving it a few playful squeezes.

“Wow!” I said quietly but enthusiastically. “You move things along quickly, Carolyn.”

She quickly replied, “I know what I want—and I’ve wanted you for a long time, Gerald. I think you are a very cute boy.” She then embraced me for a very romantic kiss. The only thing that went through my mind was that it was a shame Carolyn hadn’t been so forward with me earlier. It took a Sadie Hawkins dance for her to show her affection towards me.

When the slow song began, Carolyn and I entered the dance floor and hardly moved at all to the beat of the music. We were too busy kissing and doing other things. Carolyn continued to grope me. I figured I should partake in the same pleasure. She had not a bad build for a 14-year-old, so I helped myself to a subtle feel of her left breast with my right hand.

“It’s okay with me, Gerald, keep doing it,” Carolyn told me.

It may have been okay with Carolyn—and it certainly was okay with me—but it wasn’t okay with an alert chaperone who saw what we were up to. He gruffly ordered us to leave the dance floor about three-quarters of the way through the song. “That’s not acceptable behavior!” is the only explanation we received from him.

We weren’t exactly sure of our status. Had we been kicked out of the event entirely or just removed from the dance floor for a few minutes? The answer to that question was made clear about 10 minutes later when the next slow song was played. The same man who removed us also prevented us for returning to the dance floor. “Nope. You two are done here for tonight,” he said. Apparently, his decision was final and irrevocable.

“We that was short and sweet!” I said to Carolyn as we left the building. “I’m glad we didn’t have to pay a nickel for admission!”

“Let’s look on the bright side,” Carolyn insisted, “now no chaperone can stop us from doing whatever we want to do together.” We then had a very long kiss on the school property after which we started walking in the direction of Carolyn’s home. It was in a low-income housing unit about six blocks from the school in the opposite direction from where I lived. She insisted I come in and stay for a while.

Her mother was surprised by our appearance so early into the night. “Carolyn, what are you doing home so early?” she asked. “The dance can’t possibly be over yet, can it?”

“It’s over for us, Mom,” Carolyn admitted. “Gerald and I were told to leave by a chaperone. We were getting a little bit too affectionate for his liking.” Then she added, “By the way…this is Gerald.”

Talk about an awkward introduction!

“Uh, hello Mrs. Holmes. Nice to meet you,” I managed to utter.

Fortunately, Mrs. Holmes found the whole situation to be quite amusing. To my great surprise, she said, “I’m exhausted and I have to get up early tomorrow morning. I’m going to bed. You two can get as affectionate as you like right here. I’ll see you tomorrow, Carolyn!” She then left the room and ascended the staircase to the upper floor.

“That’s Mom for you!” Carolyn said with a bit of exasperation in her voice. “She’s about as liberal-minded as you can get as a parent.”

I was about to say something—I don’t know quite what it was going to be—but Carolyn beat me to the punch. “You heard my mother, Gerald. We can get as affectionate as we want. Would you like to have a fuck? I would!”

“How can I possibly say no?” I asked rhetorically. “Count me in!”

I figured we were both undressed before Mrs. Holmes had even gotten into bed upstairs. Carolyn had pointy boobs with prominent areolas. Her vagina had a moderate amount of hair on it. All in all, Carolyn Holmes wasn’t a bad specimen of teenage femininity. I was sporting a solid erection, which Carolyn praised as being impressive. However, she had already admitted to being a virgin, so she likely had zero other penises to use for the purposes of comparison.

Our fucking venue was an old sofa that had several teats in the upholstery. It was soft and comfortable, so nothing else about it really mattered to me. We engaged in long kisses for a while for foreplay with both sets of our hands actively wandering. I loved playing with Carolyn’s breasts. The were firm but soft. This was apparently a contrast to my equipment. “Jeez your dick is hard Gerald,” Carolyn said with admiration. I hope it stay that way for a long time.”

“You please me and I’ll please you, Carolyn!” I suggested. Accordingly, I stretched out as far as I could on the old brown couch. Carolyn got the right idea quickly and began licking and tugging on my phallus. It was a marvelous feeling. The best part was when her tongue stimulated the head of my dick. That subtle touch, I swear, made it grow even taller.

“Let’s switch positions, Carolyn. It’s my turn to please you in the same way.” Carolyn took my spot on the couch and spread her legs. I moved between her thighs and began licking her most private body part. I also found her clit with my thumb and tenderly rubbed it. Her vagina got noticeably wet.

“How am I doing?” I asked her. Carolyn’s reply was wordless. She simply pushed down on the back of my head so my face was even tighter on her pussy.” I took that as a positive sign that she was enjoying my efforts.

“I’ve licked your pussy; now I desperately want to fuck it, Carolyn. May I?”

“Of course!” she replied. “I didn’t take off my panties for just a good licking!”

I quickly mounted Carolyn for the first fuck in my life. It seemed to be such a natural and instinctive thing to do. I promptly inserted my manhood into Carolyn’s pretty pussy and began slowly moving it in and out. Carolyn seemed to know what to do too. She embraced me and together we created a lovely rhythm of thrusts. I subtly moved Carolyn from a leaning position on the couch to flat on her back to provide the finishing touches. I gave her a series of very strong thrusts, felt a huge tingling sensation with my balls, pulled out of her pussy with about three seconds to spare, and launched a sizable cum shot that ran from the top of her pussy hair all the way up to the hollow of her neck. Soon afterward I let out a triumphant groan. It was undoubtedly the most memorable life experience I’d had in my 14 years.

“Thank you, Gerald,” Carolyn said. “That was very enjoyable for me.”

I was hyperventilating slightly, so “Likewise!” was all I could manage to say.
Carolyn and I spent the next ten minutes cleaning up ourselves—and the portions of my cum shot that had sprayed further than we expected. I was dressed and headed to my home within 20 minutes of concluding the sex act. Before I left, Carolyn and I agreed to meet for more sexual fun as often as we could. Our first experience had been totally exhilarating—and we wanted to repeat it frequently.

When I got home, my mother was waiting for me. She was desperate to know how the dance went. I said, “Carolyn and I spent far more time talking than dancing.” That was factually true.

“So did you get to know her well?” Mom asked.

I cheekily replied, “Intimately, Mom! Very intimately!”