Two 14-year-olds both fancy Tammy, a girl they see on the first day of high school. She agrees to date one of them–as long as the other dates her plain friend.
Part One
My name is Steve Dennison. For most of my formative years I was raised by a single father, which was highly unusual for a boy who was born in 1962.
My parents’ marriage, by all accounts, was a huge mistake. I was conceived shortly after they met when they had a quick fling at someone’s Christmas party in 1961. When mom realized she was pregnant, they followed the custom of the day and got married very quickly so I wouldn’t be considered a bastard child. Disaster ensued. They both cheated on each other, with my father being a serial offender. My mother had very few motherly instincts, as I recall. Mom suddenly walked out on Dad and me one day when I was five, leaving a terse note for both of us on the kitchen counter that said she was “leaving forever and not coming back.” Dad’s heartfelt response was a succinct “Good riddance!”
Oddly enough, it turned out to be the best thing that ever happened to me. Dad excelled in his new dual role as father and “mother” to me, although he did it with a very masculine outlook on life. There was no way he was going to change that strong aspect of his personality.
I seemed to take after Dad when it came to the opposite sex. I had inherited my father’s good looks, even as a small child. About two weeks after Mom bailed out on us, I was invited to the home of a neighbor to have lemonade and cookies with their five-year-old daughter, who was named Cheryl. I barely knew she existed before that day as she went to a private school while I was enrolled in a public one. Cheryl took an immediate shine to me and began freely hugging and kissing me. At first, I was taken aback, but then I started to like the sensation of being mauled by this affectionate girl who was undeniably cute.
When I returned home, I told Dad what had happened. When Dad asked me what I was going to do about Cheryl’s amorous behavior, I said, “I think I’ll go back tomorrow for some more hugging and kissing.” Dad smiled, patted me on the back, and immediately declared me to be a “chip off the old block.”
Chryl was the first of about a dozen very temporary girlfriends I had between kindergarten and the sixth grade. Sometimes they approached me for romance, sometimes it was the reverse. Basically, I learned early on that I should oblige any and all girls who wanted some affection from me. “You won’t regret it,” Dad advised, “especially if they are pursing you. They will be very grateful to you for your attention. I’m sure you know what I mean.” Yes, I did.
My favorite of these young, infatuated females was a seven-year-old girl named Cindy Kravchic. Her family was of eastern European origin. To my utter amazement, when the weather turned warm, she and her nine-year-old sister paraded around their home and their backyard without tops on, just like their brothers did. When I reported this unusual but excellent behavior to Dad, he explained to me that it used to be common in North America, too “until puritanic morals slowly took over the continent.” Dad said if you visited a beach in my grandparents’ day, most of the little girls there eschewed wearing full bathing suits and only wore bottoms “until they had something worth concealing. Nobody thought anything about it. It’s still a fairly common practice in some parts of Europe.” Then he flashed a smile at me and said, “Enjoy being around Cindy while you can.” I told him that was indeed my plan. Cindy was a fun girl to hug.
Part Two
By the time I was 12, I had found a male friend who was also a romantic rival. His name was Clark O’Malley. He, too, was obsessed with girls—and told me he had been that way about as long as I had. I figured I edged Clark slightly in the good-looks department. Still, he was often linking up with the best girls at our elementary school quicker than I was because he was more assertive. It turned into a competition for us. It was completely friendly, though, as Clark and I were good buddies who had plenty in common besides precocious libidos.
On the first day of high school for the two of us, I met Clark at his home so we could walk the five blocks together and catch up with each other’s lives. Clark had been traveling with his family for most of the summer, so I ‘d seen very little of him since our eighth-grade graduation ceremony back in late June. Clark, who was now 14 as I was, reported a full summer of “carousing and occasional screwing whenever I could get it.” I reported similar activities. Clark had me beat because his travels included stops in both Thailand and the Philippines. “The girls over there are unbelievably cute and very easily persuaded,” he told me, confirming the rumors that I’d heard about that part of the word since I was ten. It was Dad who had told me about the delights of Asian girls.
I congratulated Clark on his good fortune and reminded him that today was a hugely important milestone for both of us: The first day of high school would introduce us to plenty of girls from feeder schools whom we had never seen before. “Yeah, fresh meat! Hurray!” Clark said in a joking manner—except he wasn’t joking.
By chance, Clark and I were assigned to the same homeroom. That first morning, as we were busily filling out various documents and checking to see if our schedules were correct, we both noticed a real beauty in our midst. He name was Tammy Muldoon, a breathtaking gal with curly auburn hair and other even more appealing assets. “One of God’s finest creations!” was how Clark enthusiastically described her during our first lunch period in high school.
“Yeah, I saw her, too,” I reminded him. “I couldn’t possibly miss her; nobody could. Every boy in our homeroom was gawking at her.”
“Well, that means there’s no time to waste,” Clark concluded. “I’ll see if I can get anywhere with her before the day is over.” Clark didn’t say so specifically, but I took that statement to be a challenge. He was hinting that I should do the same thing—and may the better buddy win!
We both found where Tammy’s locker was and descended up on it together. After brief introductions, Calrk boldly told her that we both thought that she was “fantastic” and we both desperately wanted to date her. I got the impression that Tammy was used to getting plenty of attention and compliments from boys, but she wasn’t aloof or arrogant about it at all. She smiled at both of us and said, “You both seem to be nice guys. You’re both quite handsome, so I have a decision to make. Let me think about this…”
Clark and I both expected she’d choose one of us and the other would be out of luck—at least temporarily. Tammy surprised us by saying that she’d go on a date with one of us as long as the other guy agreed to go on a date with her best friend at the same time and place.
I commented, “If your friend looks half a s good as you do, Tammy, I’m okay with that arrangement!”
Tammy smiled for a moment and then said, “That’s the problem. My best friend Jillian is very plain—perhaps even less attractive than that. She’s never been on a date because boys don’t find her appealing.”
“I’m still willing to agree to this proposition based on a 50 percent chance of dating you,” I said to Tammy.
“I am, too,” confirmed Clark. “Let’s toss a coin to see who will date Tammy and who will date Jillian.”
“Okay!” Tammy chimed in. “Regardless of the outcome of the coin toss, I appreciate what you guys are doing for Jillian. She’ll be thrilled.”
Tammy pulled a quarter from her pocket and set the rules. “If it’s heads, Clark is my date. If it’s tails, Steve is my date.”
I was actually nervous as the coin rose above our heads spinning wildly and crashed to the tile floor. To my utter chagrin, it came up heads. Clark was the winner and openly cheered his good fortune. I got stuck with Jillian—a girl I had never met whose best friend thought she was unattractive. You win some, you lose some.
Be that as it may, the three of us agreed to have a pizza date that Friday evening at a restaurant that was within walking distance of our high school. We’d meet near the pizza place’s front door at 6:30 p.m. Tammy would give Jillian, who didn’t attend our school, the good news the moment she got home. Tammy thanked us both and then headed off. Clark wasted no time needling me. “Fortune favors the brave, my friend,” he told me. “It’s a crying shame that you lost; it really is.” Clark put on an over-the-top fake display of sobbing and went to his locker. I threw my math textbook at him.
That night I told my father what had happened. He laughed at my misfortune, too. Then he reminded me of something he’s said years ago. “Remember when you first started being interested in girls, son?”
“You mean back in the days of affectionate Cheryl and topless Cindy?” I asked.
“Yeah, I guess so,” he confirmed. “I once told you that girls who pursue you will probably be extremely amorous and be thankful for your attention. Well, my boy, I’d bet this will be the case here with Jillian. She’ll get one look at your handsome face and fall madly in love with you. I suspect she’ll be all over you constantly. Maybe you were actually the lucky one instead of Clark?”
I gave my father a pessimistic look. “Yeah, lucky me,” I deadpanned.
Part Three
When Friday night arrived, I dressed well and prepared for a night of utter disappointment. I was going to force myself to be a good sport about dating a dud while sitting at the same table would be Clark with a fabulous girl whom I could find no fault with. To top it off, it was a rainy evening, so I needed Dad to drive me to the pizza place so I wouldn’t get soaked in the downpour. He obliged.
It turned out that I was the last one to arrive. Dad dropped me off 50 yards from the restaurant. “I don’t want to cramp your style with my presence,” he told me. At least the area was canopied so I didn’t get too wet as I walked toward the other three diners. Clark spotted me first and pointed me out to his two companions. I could see Jillian had a broad smile on her face. She was likely worried that I was going to be a no-show. I wasn’t, which pleased her. I said hello as enthusiastically as I could and we all went inside the restaurant. Clark had reserved a table for four a few days in advance.
It was quite comforting that Jillian, a 5’6” brunette, turned out to be at least average looking in my opinion. (When I thought about it later, I theorized that Tammy had likely compared Jillian’s looks to her own and the result was harsh for her friend.) Jillian was also a very good conversationalist who seemed to have a wider variety of interests and general knowledge than Tammy did. I later learned that Jillian was at or near the top of her class in virtually every academic subject at her school, while Tammy was basically a B student across the board. Still, being a typical male, I would have changed dates with Clark in a heartbeat.
As the evening progressed, Jillian became more and more affectionate, proving my father’s theory to be right. She kept moving her chair closer to mine. She’d subtly squeeze my thigh with her hand, and she was constantly giving me little hugs for no apparent reason. I quite enjoyed the unexpected attention!
Towards the end of the meal, the girls excused themselves and went to the restroom together—as girls often do. No doubt they were seeking privacy to assess Calrk and me as dates. Of course, we used the girls’ absence to do exactly the same.
“I’m quite happy with Tammy,” Clark said. That was patently obvious to me without him having to tell me. Then he added, “However far she wants to take this date tonight is perfectly okay with me.” Again, that was hardly earth-shattering news to my ears.
I think I surprised Clark by saying I was just as happy with Jillian as my date. I told him that she had been sneakily groping me for the last half hour—and it was becoming more brazen by the minute. “I’m hoping she does want to take this date as far as possible. Of course, she doesn’t have Tammy’s obvious level of beauty, but there’s something appealing about Jillian. Maybe it’s because she’s socially naïve. Whatever it is, I’d happily give her a motherhood fuck.”
“What the heck does that mean?” a puzzled Clark was quick to ask me.
“You know,” I stated. “Screw her with the intent of making her pregnant. I’ve only considered that once before in my life.”
“When was that?” Clark curiously asked me.
I recalled, “When I was 11, just before you enrolled at my elementary school, my girlfriend was Angela Capelli. She figured we were destined to be lifelong soulmates, so she wanted me to knock her up. Of course, I agreed to try. Unfortunately, I couldn’t ejaculate yet, but it was fun trying. About a month later, Angela found a 14-year-old neighbor boy who was willing and able to do the task. She vanished from the school after it became known that she was pregnant at age 11. I honestly don’t know what became of her.”
“That sounds like you may have dodged a bullet there, my friend,” Clark commented. “But why do you want to give Jillian a motherhood fuck after knowing her for about an hour? That sounds like a rash decision to me. You are usually so sensible, Steve.”
“I can’t justify it logically; it just feels like the right thing to do,” was the only explanation I could come up with. I knew it sounded crazy.
It turned out I wasn’t the only person at our table who had a crazy and capricious idea. When the girls sat down, Tammy announced that both she and Jillian thought we were wonderful dates who deserved a good screwing. “There’s no one home at my hy house all weekend, besides me, that it,” Tammy announced. “Let’s go there and do what comes naturally—engage in fucking!”
Clark and I, of course, raised no objections to that plan. As a sign it was meant to be, the heavy downpour that had been falling for three hours had suddenly ceased. We all walked at a quick gait to Tammy’s home through shallow puddles. We couldn’t wait to begin.
Part Four
When we arrived, Tammy gave Clark and me a quick tour of her family’s house. Jillian didn’t need it; she had been a visitor countless times since she became Tammy’s friend at age six. Jillian and I were told to use the guest bedroom to “get acquainted”. Tammy led Clark to her bedroom. The expression on Clark’s face was one of total elation. I tried to put Jillian, obviously a virgin, at ease my saying I’d do my best to be gentle while pleasing her with my dick. I phrased it less crudely than that, though.
Jillian smiled and said, “Steve, I want you to screw me as if you were screwing Tammy. I realize she’s more desirable than I am, so you can pretend I’m her if it will turn you on more.”
“It’s difficult to come up with a reply to that!” I said to her. “You really are a special girl, Jillian. I mean that sincerely.”
When Jillian and I got to the guest room, we noticed the bed was a bit on the narrow side. The mattress was an unusual size. It was bigger than a typical single bed, but not quite as large as a double bed. “This will be a cozy place to fuck,” I predicted.
Jillian surprised me again by saying, “I’m a genuine novice at this, but we don’t have to do all our screwing in bed, do we? There are other ways to have intercourse without lying on a bed. Isn’t that right, Steve?”
“That is very true,” I said. “I hop e to show you a few of them. Let’s both get undressed now. I’m already well aroused.”
“Are you?” Jillian said excitedly. “That’s wonderful, Steve. Let me see your dick.”
“Your wish is my command!” I replied as I removed all my clothing in about 30 seconds. Tammy even helped by pulling my trousers off as I sat on the corner of the bed. I stood up to display my partially erect penis. I was at least decently endowed. When fully aroused, I thought I had a rather formidable male sex organ—certainly thicker than the average boy my age. I knew this to be a fact from stealthily observing my peers in the changeroom for gym class. I gave my rod a few tugs to get it to stand at attention.
“Like what you see?” I dared to ask Jillian.
“Yes!” she declared. This is a first for me, but I didn’t expect your penis to be as thick as that. Is it an unusual thickness?”
“I suspect it is,” I replied. “I’ve never had any complaints about it—and I intend to please you with it. That’s my goal today.”
“Well, my goal today is to make you want to give me a good fucking!” answered Jillian, who was already halfway undressed. She finished that task by removing her bra and panties, both were pristine white. For a 14-year-old, she had at least an average build, perhaps slightly better than average. Her vagina was the “meaty” type. I was going to enjoy penetrating it–and I wasn’t going to have to pretend that Jillian was Tammy!
Jillian said nothing for the few moments I just gawked at her nude body. I think she was awaiting instructions from me. If that was the case, I was going to have plenty of fun with Jillian as a bedmate. “Let’s begin with you performing fine art of fellatio,” I told her. “It is more commonly known as a blowjob. I want you to give me one. Grab a pillow, toss it onto the floor, kneel on it and I’ll provide the required penis.”
“Sounds like great fun to me!” compliant Jillian said.
“Now just pretend you are licking a popsicle,” I told her as I presented my steadily hardening dick to her. She cautiously put her lips around its head. I moved my hips to shove it further into her mouth.
“Ah, that’s very good! Use your tongue and lips to stimulate my penis. Yes, that’s how it’s done! That’s just lovely!” I eagerly coached and encouraged this sexual neophyte.
After about five minutes of bliss, I decided to return the favor and pleasure Jillian. I told her to lie on the bed with her legs spread so I could orally stimulate her vagina. She seemed very excited about that news. I quickly positioned myself to give her private area a good licking. Jillian complained when I stopped.
“That was just the prelude. It’s time to use your vagina the way it was intended!” I noted.
That I did! I climbed aboard her and slowly shoved my manhood inside Jillian’s pussy. Her face had a look of utter amazement on it. I took it to be one of pleasure, too, as I kept pushing my penis deep in Jillian’s pussy until it could advance no further. Then I started to rhythmically screw my bedmate. It felt marvelous. It was a significantly experienced 14-year-old when it came to bedding girls, but riding Jillian was the most gratifying sexual episode I had ever had. There was just something about her to was quite appealing and made my dick rock hard. I began to fuck her progressively harder.
“Jillian, your pussy feels wonderful,” I told her as I was in the throes of passion—and I meant every word. I had sadly neglected other key parts of Jillian’s anatomy, so I stopped my thrusts momentarily to lovingly squeeze her jiggling boobs. That was an enjoyable diversion for a minute or two. Then I returned to giving Jillian the most intense round of screwing I’d ever experienced.
“I’m going to come and I’m not going to pull out first!” I warned her. If Jillian had any misgivings about that plan, she said nothing. I uttered a loud, contended groan and, as I promised, I fired my load. Jillian’s eyes widened. I kept thrusting as long as I could while I emptied my balls inside her.
“Did you intend to come inside me, Steve?’ she innocently asked me as I lied on top of her, still impaling her with my manhood.
“Yes. One hundred percent,” I honestly replied.
“It’s good thing I took a certain pill. I like you, Steve, and I like sex, but I don’t think I’m ready for motherhood yet.”
I knew Jillian had made a lot of sense. I had just been overcome with both lust and stupidity—a dangerous combination for a 14-year-old male to possess. We did take out act away from the bed as I attempted to screw her while we were both standing. It was awkward; it only worked well when Jillian leaned forward and put her hands on a writing desk, the only other significant piece of furniture in the room. I screwed her from behind, all the while fondling her breasts. I came a second time, but the volume of jism I expelled from my testicles was a mere fraction of my first cum shot. Then we got back into bed and simply kissed and cuddled for 30 minutes. All in all, it was a very rewarding first date. Jillian was pleased with how things worked out, too. “Honestly, Steve, I would have been happy tonight that you showed up for the date at all. Everything after that was a bonus for me. The last part was a fabulous bonus, I must say!”
When Clark and I eventually left the Gabriel house, Clark said that Tammy, while gorgeous, was a bit if a “dead fish” in bed. She basically was a motionless entity. Like me, Clark enjoyed girls who enjoyed having sex. Clark made me laugh we he noted, “I suppose screwing the sexiest ninth-grader in our high school was better than staying home tonight and watching roller derby on TV.”
Clark and Tammy were a couple for about a month, then they drifted apart. On the other hand, Jillian and I were a couple from that point onward. Although we attended different schools, we got together as often as possible. Her parents loved me because they figured Jillian might go through love unattached and loved. We married when we were both 22.
The next decade was filled with “motherhood fucks.” We had four children.
🔞 Candy.AI 🔥 AI Sex Chat – Roleplay, Erotic Stories, Try for Free 🕹️