My Sister's Parade of Friends

Ian is the handsomest boy at his school. When one of his sister's friends has a romp with him, she tells her friends about it. Now Ian is suddenly in demand!

Part One

Good looks seem to run in my family, particularly on my father’s side. I remember Dad being told by smitten women he encountered that he should go to Hollywood. They figured he could easily become a movie star because he was so handsome. I’ve seen photos of both my paternal grandfather and great-grandfather when they were in their twenties. They both looked very similar to Dad.

Without trying to sound immodest, I, Ian Stanton, first became aware that girls found me visually appealing in the first grade. Karen Josephs, who was a bit on the homely side, was constantly pawing me and telling me that I was “a beautiful boy.” However, I was not interested in her in the slightest. Another classmate, Barbara Melville, who was quite pretty, spent a lot of time “accidentally” touching me and giving me subtle hugs. She had curly, blonde hair and was a real cutie, so I liked Barbara’s amorous attention—even if I was just seven years old at the time.

Throughout my years in elementary school, I often received invitations to girls’ birthday parties where I routinely discovered that I was the only boy who had been invited to the shindig. It became the norm. I had no shortage of dance partners if the birthday girl decided to play records. I remember attending classmate Cindy Forrest’s tenth birthday party. Naomi, one of her cousins who was also 10, was a guest that day, too. After having known her for all of five minutes, Naomi outright told me that if I wasn’t married in a decade that she’d track me down just so we could “make beautiful babies together.” Naomi was quite a fetching young lass, so I was immensely flattered by that crazy comment. There are worse things in life than being a better-than-average looking male who is a magnet for pretty girls.

By the time I got to high school, my friend Terry Buchanan and I had the same “problem”: endless attention from smitten female classmates. I honestly thought Terry was better looking than I was. When I told him that, he laughed, smiled, and said it “was too close to call.” The ironic part is that neither one of us was particularly interested in having a girlfriend at that time. We were both top-tier students who enjoyed all sorts of other activities and pastimes. Having our time occupied by a bevy of attractive teenage girls was occasionally pleasant, but we did not want to be burdened by them and their demands on our time. Of course, if we ever needed dates for a social event or a school dance, neither Terry nor I were lonely very long. However, neither of us, by choice, entered into any long-term relationship with a girl during our four years in high school.

I had a younger sister named Emily who was quite a looker, too. My male classmates often sought her attention, but Emily was not especially interested in a full-time romantic relationship, either. Fred Symington, who was rebuffed by Emily, bemoaned the situation. He once amused me by saying, “What the heck is wrong with you Stantons? You and your sister both won the genetic lottery, but you haven’t yet cashed in your winning tickets.”

Things were about to change for me, however—thanks to my sister’s parade of school chums.

Part Two

One day I arrived home from high school to encounter Emily with a girl I had never seen before. Her name was Mandy Tetrault. With her pretty smile and burgeoning figure, I immediately thought she was an extremely attractive brunette. Apparently, Mandy’s family had recently moved into my hometown and Emily befriended her the first day she appeared at her school. I interacted with Mandy for perhaps 20 seconds. Mandy and Emily went downstairs to the rec room, while I remained on the upper floor and went to my bedroom. The acoustics in my house were interesting. The location of my bedroom one floor up from the rec room allowed me to clearly hear what was being said below. I had just opened my history text book to read that night’s assigned chapters when I heard Mandy say, “Holy smokes, Emily! Is your brother ever handsome! I’d jump into the sack with him right now if he’s interested!”

“Join the club, Mandy. At least half the girls at his school feel the same way.”

“I’m totally serious,” Mandy insisted. “Do you mind if I go upstairs and ask him?”

“Wow! You are serious!” Emily replied. None of her friends had ever been that brazen with their carnal desires towards her brother, but she accepted it. “Okay, Mandy. I’m not stopping you. When you get upstairs, walk down the hallway. Ian’s bedroom is the first room on the left.”

Mandy followed Emily’s directions and knocked on my door within a minute. Having overheard their conversation, I was expecting Mandy’s arrival. I knew what my answer would be before I opened the door.

Mandy wasted no time in asking, “Ian, this is going to sound completely out of the blue, but I want to have a fuck with you this very minute! I think you are totally gorgeous. Are you interested?”

I promptly pulled down the bedspread and said, “Please join me, Mandy. I think you are a supremely lovely girl. Yes, I’d love to give you a good fucking.”

We both undressed quickly. Mandy indeed looked wonderful in her birthday suit with her appealing breasts and slightly hairy vagina. Mandy approved of me, too—especially a certain part of my anatomy. “That’s a beautiful dick you have, Ian. But that’s exactly what I expected.” Sitting beside me, Mandy took the initiative to stroke it and caress my balls. This girl seemed to be sexually experienced. Still, I wanted to verify it.

“You’ve done this before, right?” I asked.

“Oh, you mean have sex. Yeah, sure. I’ve done it a few times,” Mandy confessed. “How about you?”

“A couple of times,” I admitted. I was being completely truthful about it. My sexual history dated back to one of those elementary school parties. One of the birthday girls insisted I linger around after all the other guests had left to have “special fun.” I was so young that although I could attain an erection, I couldn’t yet ejaculate. The second occasion was when I was 12. Therefore, with nude Mandy waiting for me to perform, I was a bit out of practice.

As Mandy continued to stimulate my phallus with her hands, I sucked on her pointy breasts. That was a real treat for me! I could have licked them and sucked them indefinitely, but Mandy raised the ante by leaning forward suddenly to perform fellatio on me. That was a new experience for me—one that I enjoyed thoroughly! I liked it so much that I returned the favor by licking Mandy’s pussy. It made her giggle, so I suppose I did it well.

As soon as I withdrew my face from her crotch, Mandy spread her legs to invite me to penetrate her. I obliged, driving my penis in her with very little subtlety. Her pussy was a tight and wonderful place for my penis to be, and we both were happily moaning, almost in unison.

“Am I pleasing you with my dick?” I asked Mandy, hoping for some positive reinforcement.

“Of course, you are!” Mandy replied. “Keep it up.”

I think that was an unintended pun on Mandy’s part, but I did keep it up in both meanings of the word. I continued to drive my solid manhood in and out of her vagina for several minutes. Finally, I felt an impending orgasm, so I pulled out of my bedmate’s vagina and spewed a sizeable load of hot jism across her belly. A few drops of semen ended up between her tits, which I now lovingly caressed as I wound down from peak sexual excitement.

“That was absolutely fabulous!” I informed Mandy. “Considering I didn’t know you half an hour ago, that was a great fuck! We’ll have to do this again…and again…and again.”

“You better believe it, Ian!” Mandy agreed with a smile. She also yanked on my shaft a few times to drain every drop of goo from my semierect rod. “I’m going to recommend you to all my friends at school. Ian, you’re too good not to be shared.”

I suddenly realized there was imminent danger: One or both of my parents might arrive home from their jobs at any time. Thus, Mandy and I hurried to clean ourselves up in the upstairs bathroom, trying to leave as little evidence as possible of our lovely carnal adventure. (I couldn’t help but take the liberty of sucking on her nipples one final time. They were that appealing to me.) Then we teamed up to quickly make my bed. We succeeded; it looked untouched. Mandy was back downstairs in the rec room with Emily when my parents arrived home in their separate cars about two minutes later. I overheard Mandy give me great praise, “Your brother has a wonderful dick, Emily. Next time, I’d like to ride it for hours and hours.” I loved this girl’s optimism.

Part Two

Mandy apparently did sing my praises to her school chums because two days later I got a telephone call from a female whom I didn’t know.

“Is this Ian Stanton? Good! My name is Jenny Flynn. I’m in your sister’s class at school. Mandy Tetrault is in my class, too. She recommended you. I’m sure you know what I’m talking about.”

Yes, I certainly did.

In a voice barely above a whisper, Jenny got straight to the point: “I’d like to get together with you for a fuck sometime soon. Does that interest you?”

Based on my very positive experience with Mandy, I now became quite interested in sexually pleasing the slightly younger demographic, so I replied affirmatively even though I had never seen this girl in my life. For all I knew, she could have looked like Charles Bronson.

Jenny suggested an unusual venue for a sexual romp—the local community center. It offered rooms for private meetings free of charge. I vaguely knew a bit about them. They were quite handy—and the price was certainly right! Students sometimes booked them for tutoring or for group study sessions. I had never heard of them being used for fucking, though. However, I was certainly open-minded about it! Jenny was apparently quite eager to enjoy what I had to offer because she reserved a meeting room from 6 to 7 p.m. that very night. I agreed to meet her there. She said she’d be wearing a tartan tam so I could spot her easily. Apparently, she already knew what I looked like.

I arrived at the community center at 6:55 p.m. I was pleasantly surprised to see a very cute blonde-haired girl sporting a tartan tam. She was patiently sitting on a chair waiting for me. She smiled warmly as I approached her.

“I assume you’re Jenny Flynn,” I surmised. “Is that right?”

“Yes, I’m Jenny—and I know you’re Ian.” She added, “I’d know you anywhere.” How this was the case I did not know.

I replied, “Well, Jenny, you are quite beautiful. I’m going to enjoy our little get-together very much. I’m sure of that!”

“We have conference room #4 booked for 60 minutes,” Jenny informed me. She whispered, “I brought along some of my schoolbooks. This way it looks like we intend to study instead of fuck. It just looks better.” She pointed to a bulging knapsack.

“Hey, I should have thought of that, too!” I told Jenny. “Let’s go to Room #4 and have some fun. That’s why we’re both here!”

I had never been inside one of the conference rooms at this facility, therefore I was impressed when I first saw Room #4. It had chairs and tables to accommodate about 20 people. There were also a couple of plush armchairs that would best suit what Jenny and I were about to do. Jenny shut and locked the door behind me. There were no windows at all for prying eyes to see our shenanigans.

Jenny removed her jacket to reveal a pristine, white blouse. She was bustier than I expected, which was a great surprise. She had a pleated red skirt and matching knees socks. Combined with her tam, Jenny looked as if she were wearing some sort of uniform. I found that to be surprisingly sexy. I myself had dressed decently, putting on a shirt and a sweater with gray dress slacks and leather shoes. I quickly removed my entire ensemble.

I observed Jenny unbuttoning her blouse. When she exposed her brassiere, I distinctly felt my penis rise. This girl was even better looking than Mandy Tetrault—which was saying something! She was about to undo the clasp of her bra when I asked, “May I have the honor, Jenny?” She smiled and said yes.

I was now completely unclothed as I approached Jenny. I saw her look down at my erection and grin. I put my arms around her—she was about 5’3”—and undid her brassiere which fell to the floor. Jenny’s breasts were lovely for her age. I tenderly cupped them and then put my face between them. “Great boobs, Jenny!” I informed her as I licked the left one. Jenny then stepped out of her violet-colored panties. She had only the slightest hint of hair on her vagina. I was about to lift jenny off her feet and carry her to one of the large, soft chairs, but I didn’t get the chance. Jenny immediately dropped to her knees to give me a blowjob. I liked this girl already!

“Mandy told all of us at school that you had a pretty dick, Ian. She wasn’t exaggerating!” Jenny stated. Jenny gave my shaft a through licking and even sucked on my testicles. This beautiful blonde girl was clearly no sexual newcomer, either! I only stopped the wonderful blowjob to place my dick between Jenny’s lovely tits for a brief titty fuck, which amused her. Then I picked her up and moved her to a soft chair.

I sat down and set Jenny on my lap. I said to her, “I think the best way to do this is for you to ride me, Jenny. Is that okay with you?”
“Absolutely!” she exclaimed. “I was about to suggest this myself.” Jenny climbed abord my dick immediately. The sensation was heavenly. My penis was totally rigid and went as far up inside her vagina as possible. It was literally balls deep! I grabbed her by the hips to guide her up and down. I also pulled her forward slightly so I could suck on Jenny’s treasures. I figured every boy in her class probably wanted to screw this sexy vixen. Therefore, I was extremely flattered that she specifically had sought me out for sexual pleasures based solely on Mandy Tetrault’s glowing review.

“Ride me until I come, Jenny! It won’t be long from now,” I told her. I was right.

Within about two minutes I could feel the stirring that every male easily recognizes when an orgasm is mounting. I pulled out of Jenny’s pussy, intended to come on her lovely tits, but she had other ideas. She grabbed the shaft of my penis and aimed it at her own face. I got the general idea and fired my load, most of which struck Jenny’s forehead and left cheek. My goo sexily dripping down this teen beauty’s face was a truly magnificent sight. A second rope of my cum struck her on the chin and neck. Jenny Flynn had drained my testicles within seven minutes!
Jenny went to her knapsack to get something. She had been well prepared because she produced a fresh roll of paper towels to clean up the mess on her face and the surrounding area. Jenny smartly had also brought along a plastic bag for the used towels. When that chore was done, I signaled Jenny with a wave to return to my lap. “Just because you made me come so quickly, that doesn’t mean we’re close to being done here,” I told her.

“I was hoping you’d say that, Ian.”

“Let’s smooch,” I suggested. “It doesn’t seem right that your rode my dick—excellently, I’d like to say—before we even kissed. You have such a pretty face, Jenny. I can’t help but want to kiss it.” My comments put a smile across it. Jenny embraced me and we kissed romantically for about 20 minutes. The sensation of her terrific breasts pressing against my chest was an added bonus.

After a while I told her, “I didn’t get a chance to lick your pretty pussy, Jenny. I’ll do that now, if you like.”

“Yes, please, Ian!” she said without hesitation. Jenny sat on the plush chair, spread her legs widely and I went at her pussy with great gusto. It had been wet from our intense fucking, so I lapped up her vaginal discharge with alacrity. I pronounced it to be “very tasty” just before she came a second time. Jenny got more paper towels to deal with that unexpected squirt.

We still had about half an hour left in the room rental, so I just had Jenny sit on my lap while we chatted. She merrily caressed my penis while I fondled her tits. It was great fun.

Jenny explained that she had known who I was since we were in elementary school, although she was two years younger than I was. “You know what, Ian? I used to gawk at you at recess time because you were so handsome, even back in those days. I told my mother that my goal was to marry you someday. Fucking you is a good consolation prize, though.”

I said, “Hey, the two of us getting married is still possible, Jenny. I could do a hell of a lot worse than you. You are so gorgeous that you make my sister look second-rate. Nevertheless, can we schedule another fuck sometime soon? I’d like that!”

Jenny said with a scowl, “Unfortunately, I have to wait for my turn again, Ian. That might be a long time from now. After what Mandy Tetrault told us, there’s a whole parade of girls who want to have a fuck with you. We decided that every girl who was interested would get to have one romp with you before anyone got seconds. We drew lots for the order. I drew lot #1. That meant I got to call you first, so I did.”

I was flattered beyond belief that I was the subject of a sex lottery for horny teenage girls. I had to ask, “How many girls from your class are involved in this lottery, Jenny? I must say I’m very curious to find out.”

Jenny pulled out a sheet of lined paper from her knapsack and began counting. “As of today, it’s 23. However, I guarantee that total will go up when I share my review of you with all the girls I know at school. I hope you have a lot of free evenings, Ian. You are very much in demand!”