My Sister's Nerdy Friend

Donna's friend Arlene is the biggest nerd at middle school. Arlene gets no invitation to a dance, so Donna recruits her 20-year-old brother to romance her.

Part One

"So what do you say, Jeremy? Will you do it?"

I, Jeremy Saunders, thought about it for a few seconds before giving my sister Donna this affirmative reply. "Yeah, sure. Why not? I've always been kind of fond of Arlene even though she's a bit odd and quirky. Okay, I'll romance your friend for an evening. Who knows? A one-off date with Arlene just might be fun."

With that utterance, I had just agreed to spend a romantic evening with my sister's longtime, peculiar friend. Her name was Arlene Garland.

Let's back up a bit so I can give you some necessary background about me and Arlene. It was the spring of 1970. At the time I was 20 years old. I had just recently moved into my own small apartment because that's what 20-year-olds did in those days when they had the means to do it. I had been employed as a copy editor and general columnist on my small town's semi-weekly newspaper for about a year, and I now had enough disposable income to pay for my own modest abode, which was located in a new block of flats. The building where I now lived had once been a bicycle factory. It had stood vacant for at least a decade before some enterprising individuals turned the space into small dwellings for renters such as I was.

I had been living on my own there for about three months. I liked the independence of being by myself--although I seldom ever was. My little sister, Donna, was always dropping by. (I strongly suspected my mother put Donna up to it to make sure I wasn't starving to death or living like a pig. I was doing neither.) My friends also visited me frequently. They were impressed that I was now a full-fledged bachelor with my own private "pad". I had no girlfriend at the time, so any wild romps they suspected me of having were only in their fertile imaginations.

Arlene and my sister were both 14 years old and students in the same eighth-grade class at the middle school I had once attended. Arlene was a stereotypical nerdish girl—and had been since the day I first met her when she was six and I was 12. She was an only child, the daughter of two university professors. She was an amalgam of her parents, so I was told. I had no reason to doubt that. Arlene wore fairly thick eyeglasses, dressed very conservatively, braided her long hair, and talked only about scholarly things. My parents amusingly characterized Arlene as "being six but going on 40." It was a fair assessment. For her teachers, Arlene must have been a pleasure to have as a student, but she was certainly considered an oddity by her peers. When she was in the second grade, Arlene and her classmates, as an early public-speaking exercise, had to stand at the front of the classroom and deliver an impromptu talk to everyone for at least 60 seconds about their favorite things to do. Most of the other kids in the class predictably spoke about their favorite toys or television programs. Arlene, however, spent more than eight minutes enthusiastically rambling on about how much she loved going to museums—which was quite an unusual pastime for a seven-year-old girl. According to Donna, Arlene would have gone on indefinitely, but her teacher saw the other students were bored out of their minds listening to her long, meandering monologue, so she put a sudden halt to Arlene's oration.

Donna may have been Arlene's only true friend. Donna was a "mother hen" type who always stood up and protected the outsiders at her school—which Arlene was clearly one. Arlene frequently visited our house as my sister's guest. Despite our difference in age, Arlene enjoyed my company and regaling me with long talks about subjects she had just learned by randomly opening up pages in the World Book Encyclopedia. Often, I knew or cared nothing about the topics she was regurgitating, but I feigned interest in whatever it was just to please my sister. Arlene was very happy, too. "Your brother is such a good listener," I once overheard Arlene say to Donna when she was about nine. "I like him! It's a shame he's not in our class, too. He’d be my boyfriend—for sure."

As Arlene matured, she had no luck at all getting boys interested in her. To them, she was the "ultimate nerd and someone to be avoided” Donna sadly told our family. Therefore, Arlene never got invited to school dances or anywhere else. On a few occasions, Arlene went on her own to a dance but sat by herself as a wallflower for the entire time. After three such negative experiences, she gave up trying. You could hardly blame her for being discouraged. Arlene confided to Donna that she had no intention of going alone to the major eighth-grade dance—the last big social event of the school calendar. It was too depressing for her. Donna was saddened but not truly surprised by this news, just because she was a highly empathetic person. In response, somehow Donna came up with the crazy idea that I should take Arlene on a romantic date on the night when just about every eighth-grade pupil would be at the school dance—just to cheer her up. That’s why she asked me the question that began this tale.

Part Two

Arlene knew nothing about Donna’s intervention into her social life, but she was thrilled by its outcome once she learned about it. She quickly agreed to have a date with me on the same evening that the school dance was taking place. Arlene lied to her parents, saying that she was going to the dance, as they may not have allowed her to have a night with 20-year-old me if they knew the truth. In my mind, Arlene was in no danger of losing her virtue. I figured I’d take her to dinner and perhaps to a movie—and my good deed would be fulfilled. As it turned out, Arlene had other plans for me, however.

There was another ruse involved. I picked up Arlene with Donna in my car, too. Arlene had told her folks that I was treating both her and Donna to dinner at a restaurant before the dance. As soon as Arlene got into the car, I drove Donna back home. Then I took Arlene to a popular diner for a meal. Clad in a very expensive, lacy party dress, Arlene was easily the best dressed person in the eatery.

We ordered two tasty roast beef dinners, large soft drinks, and pieces of chocolate fudge cake for dessert. Arlene, quite talkative as usual, spent most of the time talking about various odd religions she had come across during her vast reading. When I got a chance to speak, I asked Arlene what she wanted to do for the rest of the time until the approximate hour when the dance would be concluding. I fully expected her to choose a movie to see or something along those lines. Instead, Arlene suggested we just go back to my place and watch television.

“You’re a very inexpensive date, Arlene!” I kidded her.

“I just know what I want tonight, Jeremy,” Arlene said. I took that as an innocuous comment.
After we drove to my place, I expected Arlene to tell me there was some type of highbrow documentary on television, but she surprised me by talking about something very earthy—human sexuality.

I don’t think half a minute had elapsed before Arlene asked me, “Jeremy, did you know that males attain their peak of sexual performance usually around the age of 19, but women don’t get there until their mid-thirties?”

“I didn’t realize I was over the hill at age 20,” I quickly replied in a sarcastic manner.
Arlene was just as swift with her next comment. “Age 19 is just an average, Jeremy,” she told me sympathetically. “I bet you are sexually excellent at age 20. In fact, I want to find out right now! Can I have sex with you, please?”

I was startled, but nothing should have startled me that involved Arlene Garland. All I managed to say as a reply was, “Arlene, you definitely surprise me!”

“Jeremy, If I had been a 20-year-old instead of just a 14-year-old, what do you think my asking to go back to your apartment instead of a movie would have meant? Wouldn’t you have assumed I wanted sexual intercourse?”

“You always ask great questions, Arlene,” I informed her. “That’s never changed with you from the first day we met. You’re absolutely right. Yes, if you had been 20, I’d have assumed you wanted to have sex with me.”

Arlene reminded me of the law at the time. “I’m 14 now, so it’s not illegal for you to have sex with me, Jeremy. I’ve never had sex before. I want to try it with you. I’ve always liked you a lot because you are so friendly and such a good listener.”

“Well, Arlene, I’ve always liked you the best of all of Donna’s many friends. You are definitely unique—that’s for sure,” I told her. I meant that as a compliment.

I waited for her to say something else, but she didn’t. She just looked at me with a fixed, hopeful expression on her face. I gathered that Arlene was wanting a definite reply from me about what would be happening in my apartment. “Okay,” I finally said. “Arlene, you want sex from me, so that’s what you’ll get from me! But I will be as romantic as possible. Screwing for the sake of screwing is really just biology. When you include a bit of affection, it’s much more satisfying. You’ll see.”

Arlene just glowed. “You’re a fun first date, Jeremy!” she said with a coy smile.

I led her to my small bedroom. I had just a single bed, but that was okay for screwing a petite girl. Arlene fit that description; she was only about 5’2”. The first thing she did was undo her braids to allow her auburn hair to fall freely behind her. I had never seen her without braids before. Her plain looks immediately improved by at least 50 percent in my estimation—and I told her so. “Lose those silly braids forever, Arlene, and you’ll probably have numerous eighth-grade boys swarming all around you!”

Arlene grinned and said, “You really think so, Jeremy?”

“I know so!” I told her.

I watched her slowly remove her lacy party dress. I couldn’t help but notice during dinner that her dress was designed to show a bit of cleavage. Arlene was average in the tit department for her age—but that was news to me because she had always dressed so modestly before that I could not gauge how blessed she was in the bosom. When she was standing before me in only her beige brassiere and her baby blue panties, I asked her to stop disrobing.

“Arlene, let me get down to my briefs and we can remove the final garments from each other,” I suggested. “That’s always part of the fun.”

Arlene nodded her assent and I rushed to get down to my skivvies. “Let me undress you first, please, Jeremy. I can’t wait to fondle your penis. I bet it’s impressive.”

I agreed to Arlene’s flattering request, but I sensed she would be disappointed in the size of my semi-erect phallus. My drawers came down just as my penis was rising to its fullest potential. “Ooh, that is a nice one, Jeremy. I like it!” It occurred to me that the precocious, 14-year-old virgin who had just removed my underwear likely had seen no other male sex organs up close to make any sort of meaningful comparison. I thought that was a lucky break! None of the half dozen girls I’d been intimate with since the age of 13 had ever worried about my dick size overwhelming them.

Arlene began to give my stiffening shaft a few gentle strokes when I politely reminded her that I was waiting to remove her undergarments, too. I stepped behind Arlene, unclasped her bra, and let it fall to the floor. I gave her young breasts a couple of gentle, loving squeezes before I slid her panties down to her ankles. I gave her butt cheeks the same type of fondling and then I spun her around so I could fully examine the front side of her physique. I was very pleasantly surprised at what I saw: Arlene had a hairy pussy and two very lovely breasts. All in all, she was quite an attractive girl when she literally let her hair down and showed off her assets. Those eighth-grade boys had no idea they were missing out on a real cutie!

“What a nice body you have, sweetheart!” I said to her as I lifted her off the wooden floor and set her on my bed. I immediately fell upon her and embraced her appealing body. I gave her a series of short kisses all around her neck and face, culminating in two long, romantic ones on her lips. Arlene obviously approved because she was in no hurry to move on to anything else.

“I’m going to make you feel excellent, Arlene,” I said to her truthfully. “That’s my main goal this evening—to please you completely. I’ll start by licking your lovely pussy. I suppose I’m the first male who will enjoy that pleasure, right?”

“You’re the first male to do anything with me!” Arlene responded. I suspected that was the case.

With the use of my bed’s two pillows, Arlene propped herself into something close to a full sitting position. I slithered upward and placed my face where it needed to go for an act of cunnilingus. Her pussy was surprisingly tasty. (In the past, I’d sampled some that weren’t!) I had a decent-sized tongue, so I put it to the best use possible, licking every possible millimeter of Arlene’s most private part. When I slid a finger—and then two—inside her vagina I was rewarded by a stream of liquid. The virgin Arlene had attained an orgasm from what I considered to be just a slight bit of stimulation. Arlene moaned with delight as she let loose. Then she felt the need to apologize to me for her release.

I stopped her in mid-sentence. “Arlene, don’t you dare apologize for having a come!” I told her promptly. “That’s a great compliment to me—and it’s a harbinger that you will be a great sex partner.”

I moved further up Arlene’s now slightly sweaty body so I could enjoy her tits. They were far from being huge mountains, but they weren’t invisible either. Arlene’s breasts fit her torso just right, in my humble opinion! She had small areolas—which I preferred. Her nipples took a bit of working on to get them hard. I was only too happy to put in the extra effort. Once they became pokey, Arlene’s treasures were superb sex objects for me to play with. I intended to give them a titty fuck before the night was over, but I had promised Arlene that my task was to please her. Fucking her boobs, even for just a few seconds, would have only pleased me. Still, I hoped to get the chance to engage in one of my favorite sexual desires with Arlene’s tits.

I moved up until we were face to face again so we could share a few more romantic kisses and I could whisper sweet nothings into her ear. When I finally said something that made any sense, it was, “Time for me to fuck your pussy, Arlene. I’ll be as gentle as I can, but I guarantee you’ll like the feeling.”

“Yes, please do that, Jeremy!” replied Arlene. “Give be the best fucking you can.”

Before I got the chance to insert my penis into Arlene’s pussy, she insisted on giving it a few more strokes to make it as rigid as possible. “That dick of yours feels so wonderful, Jeremy. It must feel really good for you when it’s that hard.”

“I feel like I’m carrying a loaded pistol right now,” I told her. “It’s ready for action—and it needs to be fired! It’s definitely time for the fucking you came here to get!”

Arlene spread her legs invitingly. For fun, I gave her pussy one last lick. “For good luck!” I said to her with a smile. Then I slid my shaft inside her slowly. I made a point of watching her face as I entered her. Arlene’s eyes widened noticeably. She gasped for a moment and then started to breathe rapidly. A Look of utter amazement came over her face.

“Like it so far?” I asked my glowing bedmate.

“This is the best feeling ever, Jeremy! Having a fuck with you is a thousand times better than going to that silly school dance tonight!”

I thanked her for the kind compliment. I had merely entered her vagina—I hadn’t yet begun to truly please my youthful sex partner with my stiff dick. I grabbed her by the hips so I could begin a strong thrusting motion inside her. It felt great to me. Judging by Arlene’s facial reaction, it felt out of this world to her. She wrapped her legs around me so I wouldn’t stop screwing her. She began repeating the word “Yes!” over and over so I knew I was fulfilling my promise to make this night of sex memorable for my sister’s nerdy friend.

Arlene had at least one further orgasm. When she said, “Jeremy, keep fucking me until we both die!” that strangely was the catalyst for my ejaculation. I pulled out of Arlene just in time to launch a shower of warm, white goo across her upper torso, with some of my jism even striking her left cheek. This time I was the one who let out a series of contented sounds. These were a combination of moans and chuckles. “That’s what you call a major cum shot, my dear!” I told her. I wasn’t lying. It was undoubtedly the most intense orgasm I’d had since reaching puberty.

“Is it over now?” Arlene asked me with a disappointed tone in her voice.

“Not if you don’t want it to be!” I replied. “Arlene, I figure we still have at least an hour before the dance breaks up at your school. We can keep fucking to pass the time. I take it that’s what you want! Am I correct about that?”

“Yeah, absolutely!” she responded. Then Arlene sweetly inquired, “Jeremy, is there anything I can do for you sexually after all you’ve done for me so far?”

“Well, since you asked me, yes there is,” I told her. “Actually, I have two sexual requests to make. Once my dick gets hard again, I want to fuck your tits. That’s one of my favorite sex acts. I want to straddle you and set my rod between your boobs. You squeeze them together and I slide my penis up and down. It makes for a great visual! It always excites me!”

Arlene said, “That’s fine with me. Let me get your penis hard again, Jeremy, by sucking on it!”

We switched places so I was lying on the bed with my head resting on the pillows. Arlene was performing fellatio on me quite passably when she suddenly stopped to ask me a question. “Oh, you said you had two sexual requests for me. You mentioned the titty fuck. Jeremy, you didn’t tell me what the second one was.”

I laughed and said, “The second request is exactly what you’re doing to me right now! Arlene, I wanted you to get my penis hard as a rock again with a blowjob! You really are a terrific sex partner for a first-timer!”