Flirtatious Fiona

Fourteen-year-old Connor's friend's sister (Fiona) is an unabashed flirt. After four years of cuddling, they advance to sex under very unusual circumstances.

Part One

When I was age 14 and began high school in 1976, my best friend was Frank Valleri. We couldn’t have been better matched. We both were better-than-average students. We shared the same sarcastic sense of humor. We enjoyed sports and games of all types. We were highly competitive when we played tennis, checkers, or any board game. We also had a passion for American college football—which was rare among Canadian boys in those days. Hardly a fall Saturday went by when Frank was not at my house watching one or two games on TV—or I was at his for the same purpose.

It was during my first “college football road trip” to Frank’s house that I met his younger sister, Fiona. (Frank had three siblings whose names all began with F.) She was a cute, 10-year-old who wore her dirty blonde hair in pigtails and dressed, in my opinion, slightly younger than her age. She was also very forward, not the slightest bit shy or reserved around people she had just met.

Frank and I were watching Penn State trounce an overmatched opponent. He was seated on a chair. I had the large couch to myself—until Fiona showed up. Fiona took one look at me and asked her brother, “Who’s your handsome friend, Frank?”

That question, coming from the lips of a precocious fifth-grade pupil, caught me well off guard. Normally I am quick-witted, but I had not expected such a flirtatious comment from a little girl I didn’t even know in the slightest.

“Fiona, this is Connor Harrington, my buddy from school. I guess you haven’t met him yet. Connor, this is my sister, Fiona. She’s 10 going on 35. She’s never met a high school boy she didn’t like.”

“That’s not true,” Fiona stated with a bit of defiance in her voice. “There are a couple of high school boys who live on this street I don’t like at all. I do like Connor, though. He’s a very cute boy.”

“Glad to know you, Fiona,” I said, failing to suppress a laugh. “Thanks for the kind compliment. You’re a real cutie, yourself! It’s a shame you’re not 14 like I am. We’d make a lovely couple!”

Fiona, without being invited, promptly sat beside me, and gradually narrowed the distance between us until our hips were touching. That took about 20 seconds.

“Fiona, you don’t like football or even understand it,” Frank said. “What are you doing here?”

“I want to get to know Connor, of course,” she said without reservation. “Any friend of yours, Frank, is a friend of mine!”

“I think you now have quite a good idea what Fiona is like, Connor. She knows what she wants, likes what she sees, and acts accordingly. I worry Fiona is going to end up like her older sister, Frances—pregnant at 18—because Frances was obsessed with teenage boys, too.”

Fiona was no longer listening to anything her brother was saying. Instead, she was fully snuggled up against me, her arms lovingly wrapped around me, and her head resting on my right shoulder. I’d never encountered such as assertive girl in my life--but I liked what was happening!

Frank tried to admonish his sister for her flirtatious behavior. “Fiona, I’m sure Connor doesn’t want you crawling all over him while he’s trying to watch a football game with me.”

“Oh, is there a football game on TV?” I asked jokingly.

Frank threw his hands into the air and said with a tone of exasperation, “I could be wrong about that, however.”

For the next three hours, Fiona did not move from the couch. I wasn’t much different. After a few minutes, I affectionately wrapped my arms around Fiona in return. Frank and Fiona’s parents had met me before. When they returned from a shopping outing and saw their daughter practically sprawled across my body, Mrs. Valleri simply stated, “Oh, look! Fiona’s made a new male friend. That’s par for the course.” Then she and her husband went into the kitchen. Frank followed them to help put away the groceries they had bought. He was out of the room for about five minutes. Fiona took the opportunity to sweetly give me a series of kisses on my cheek. I thanked her for them and gave her a quick kiss on the lips.

“You will be my boyfriend someday, Connor,” she predicted. “I just know it.”

I was reluctant to admit it, but that was the most enjoyable college football game I had ever watched in my 14 years. Five minutes after it ended, I couldn’t remember a single thing that happened in it. I was reasonably sure that Penn State had won, but no details at all came to my mind. I had been thoroughly preoccupied by young Fiona Valleri’s attention to me.

Part Two

Over the next two years, whenever I visited Frank’s home for any reason, I could be almost certain that Fiona was not too far away. When no one was looking, we hugged and exchanged quick kisses. One day when I was 16, I came to Frank’s house to watch a baseball game on TV. It did not take me long to notice that Fiona was conspicuously absent. Frank noticed what I had noticed.

“Tough luck, Connor,” he told me with a laugh. “Your unofficial little girlfriend has gotten herself a boyfriend her own age. She’s at Tommy’s house this very minute, no doubt cuddling the overmatched 12-year-old into submission.”

“It’s a sad day when Fiona prefers a 12-year-old cuddle partner over 16-year-old me!” I joked.

The following week when I was again watching a sports event on TV at Frank’s house, Fiona took her regular spot beside me on the couch and began pawing, groping and cuddling me as usual.

I was puzzled, so I asked her, “Hey Fiona, I thought you had a boyfriend now—and here you are snuggling up with me again. Did you break up with Tommy?”

“Oh, no,” she quickly replied. “Tommy and I are still together…and you’re still you. What Tommy doesn’t know can’t hurt him. I just love having you in my arms, Connor. I’ve always enjoyed it.”

“Yeah, I believe I’ve noticed that,” I said to her. Then I kissed her on the lips. Frank saw it.

“I knew this would happen someday,” he said while shaking his head. “I’m going to have to douse you two with cold water if this continues.” As usual, Fiona paid no attention to her brother and spent another sports event pressed against my body for hours.

Part Three

From age 12 to age 14, Fiona, by Frank’s estimation, had had eight different boyfriends, some of them three years older than she was. None of those relationships came close to stopping Fiona from continuing to romantically maul me at every possible opportunity whenever I visited Frank. I had quietly enjoyed her affectionate behavior at age 10. By the time she was 14, I absolutely loved it. She had developed into a strikingly attractive eighth-grade girl. She had become a tremendously fun person to hug. When we were alone together for a few minutes, sometimes my hands drifted into various appealing and private parts of Fiona’s blossoming anatomy.

“Don’t be shy about it, Connor,” she once advised me. “If anyone is entitled to feel me up, it’s you!”

“Yeah, but I’m 18, Fiona, and you’re just...”

“Connor, my short-term boyfriend last summer was 17. Allen and I did more than just sit on the couch and hug.” That statement—and the visual images it created in my mind—startled me, but then I remembered what Frank had told me four years ago: Fiona was going to end up like her promiscuous older sister as they were clearly wired the same way.

In 1980 I got a Baseball Encyclopedia, a huge and expensive book, as a graduation gift from my aunt and uncle. It was an invaluable source of stats and information in the days before the Internet changed society. The next time I was at Frank’s house, I brought it along with me to show it to him. He was plainly jealous that I had such a resource at my fingertips. Stupidly, after we had watched an exciting baseball game, I left it behind. It wasn’t until the next morning that I realized I had forgotten the book. I phoned Frank immediately to alert him.

“I know why you are calling, my absentminded friend,” he said without me saying anything but hello. “Your precious Baseball Encyclopedia is safe. You can come and pick it up anytime you like. It’s on the coffee table near the TV set. I’m about to head out in a few minutes from now, but you can drop by the house and pick it up whenever you want. Don’t even bother to knock; the front door is unlocked. I won’t likely be home until late tonight.”

About an hour elapsed before I walked the five blocks to Frank’s house. As instructed, I didn’t knock. I entered unannounced, walked a few feet down the hallway, made a right turn into the Valleris’ TV room…and saw 14-year-old Fiona Valleri being ridden by a boy who looked to be about the same age! Of course, neither of them had a stitch of clothing on. Fiona didn’t seem to be bothered much by my untimely intrusion, but her young lover immediately went into full panic mode.

“Please don’t kill me for fucking your little sister!” he pleaded. “I’m sorry! It won’t happen again, sir. I promise! Honest!”

“Calm down, Brad,” Fiona told him. “He’s not my brother; he’s Connor Harrington, my brother’s friend. I like him a lot, too.”

Brad rushed to cover himself up with his discarded clothing, but Fiona leisurely laid on the same couch we had used for our numerous cuddling sessions since 1976. Buck naked, and seemingly unconcerned by it, Fiona was quite an appealing sight to this 18-year-old male.

I explained I had dropped by to pick up my book, and that Frank had told me to just walk into the house without knocking. “Sorry If I startled you two—especially you, Brad. That’s your name, right?”

Brad shyly nodded to indicate I was correct.

“Brad Miller is in my eighth-grade class, Connor,” Fiona explained. Somehow, I was paying attention to what she was saying, despite the obvious distraction of Fiona’s nude body. “My parents left us alone to visit friends. No one else was here, so this is the first time we’ve fucked. We were having a wonderful time, too. Right, Brad?”

“Yeah, I guess so,” the eighth-grade boy sheepishly said.

“You guess so?” Fiona replied. “You’re not sure about it? Brad, you seemed to be having a great time about three minutes ago when you were shoving your erection inside me.”

“Lucky you, Brad!” I interjected. “I’ll just grab my book and leave you two alone to finish doing what you were doing.”

Fiona asked me with a bit of worry, “You’re not going to tell my parents or Frank what you saw here, are you Connor?”

“Oh, no,” I stated. “I didn’t see a thing…but I do wish I was the guy riding you, Fiona. You’re awesome in your birthday suit. Just fabulous.”

I picked up the heavy book. I had taken about three steps toward the door when I heard Fiona make a wonderfully lustful suggestion. “Why don’t you join us, Connor? You two guys can share me. Wouldn’t that be great fun?”

I was shocked by Fiona’s terrifically enticing offer, but I managed to keep my wits about me. “I’m interested,” I said after a few seconds. “It’s a heck of a step up from cuddling on the couch together or occasionally feeling your tits, Fiona. I don’t want to infringe on Brad’s territory.”

Brad was about to give his opinion, but Fiona spoke first. “If Brad wants to continue to be my boyfriend, he’ll have to go along with this. Connor, I’ve wanted you to fuck me since that day we first met. If it takes a threesome today to achieve that, I’m more than okay with it.”

Brad didn’t openly agree with Fiona’s sexy plan—but he didn’t openly object to it, either. Therefore, I took his silence as a tacit yes. I undressed in about 15 seconds.

Part Four

This was something new for all of us. Since I was the oldest, I took charge of things. My first instruction was, “Brad, get back on top of Fiona and keep fucking away until you come. I’ll amuse myself with Fiona’s lovely tits while you screw her.”

That was what we did. I knelt near the upper part of Fiona’s sexy body with Fiona lying on her back on the couch with Brad on top of her. Brad grunted considerably while he fucked. Meanwhile, I merrily played with Fiona’s breasts. They were quite lovely body parts for a 14-year-old girl. (No wonder she had a long list of past boyfriends.) I got her nipples very aroused and then sucked on them for my reward. My dick was as stiff as it had ever been. I rubbed it against her tits and them placed it in Fiona’s mouth. She had given it just a few sucks when Brad let out a loud moan. He had clearly ejaculated inside Fiona’s vagina. He quickly pulled out, and most of his jism dripped onto the brown leather couch. Panicky, he promptly grabbed a box of tissues and cleaned up the mess. He also wiped Fiona’s pussy clean, which was a very thoughtful gesture.

I announced, “Time to change places, Brad! While you’re recuperating, you can have fun with Fiona’s perky boobs. I can attest they’re quite lovely objects to play with.”

I quickly mounted my longtime cuddle buddy and enjoyed her carnally for the first time ever. Brad certainly knew a good thing. Fiona’s vagina was moist and marvelous. I shoved my manhood in her quite easily. (I suspected that Fiona had far more sexual experience than I had despite the fact that I was four years older than she was.) The sensation was a little bit odd because I could definitely feel the remnants of Brad’s recent cum shot inside Fiona’s pussy. Oh, well! That was certainly a bit of a turnoff for me, but not enough of one to stop me from vigorously screwing my best friend’s horny little sister with great gusto.

Brad was exhausted from his earlier carnal efforts and did not enjoy Fiona’s chest as much as I anticipated. Accordingly, I asked him to move aside so I could give Fiona the full fucking that she so richly deserved from me. Brad complied without any fuss.

I instructed Fiona to get on her knees so I could fuck her from behind. That was marvelous as every inch of my shaft went fully inside Fiona’s vagina. It felt wonderful, despite the fact it was wallowing in Brad’s cum.

“That’s the way to do it,” Fiona declared. “It feels great having your hard dick inside me, Connor—but I always knew it would.”

I replied, “Aw, hell. I guess I should have fucked you when you were ten, Fiona. You would have been worth the jail time if we had been caught.”

Fiona did not respond to my comment—for good reason. Brad had resumed his part in the threesome by putting his semi-erect penis in Fiona’s mouth. I thought that was a very sexy sight being so close to what I was doing at the other end of Fiona’s beautiful body. My brain went into sensory overload which meant I was about to come. I told Fiona she had put me over the edge. Like Brad, I groaned loudly and fired my goo into Fiona’s welcoming cunt. Unlike Brad, I kept my dick inside her for at least five minutes, giving Fiona a series of gentle, short thrusts until it became flaccid. I fondled her breasts all the while. When I finally dis engaged, both Brad and I caressed our shared lover, plastering Fiona with kisses all over her body. It was the first time I noticed that Fiona had sexy little toes to go along with her more obvious sexy body parts!

After about 20 minutes of post-coital activities, I said, “I should be getting home. Have fun with the rest of your afternoon, you two. It’s been a highly enjoyable experience for me.”

“Don’t forget your baseball book, Connor,” Fiona reminded me.

“I’ve got it,” I told her.

“Come by again soon and leave behind something else, Connor,” Fiona said to me with an impish smile. “That way we can do the same thing as we did today when you have to come back to retrieve it.”