A 12-year-old boy’s first girlfriend has an amorous little sister who fancies him too. Fifteen years later, the circumstances allow them to get together.
Part One
My name is Danny Cooper. I acquired my first real girlfriend in 1976 when I was in the sixth grade. (That was 50 years ago. Time flies!) She was a classmate of mine named Mandy Thomas. My mother was the catalyst for this happening.
One day our teacher, Mr. Preston, gave the class a social studies assignment that required us to work in pairs. We were free to select our own partners. As was becoming a common occurrence in our class, the moment after Mr. Preston said we had to work in pairs, Mandy asked to be my partner. The two of us were among the best students in the class, so I welcomed working with anyone who wasn’t a complete airhead. Mandy certainly met that standard.
When I got home that day, my mother gave me the standard, “What happened today at school?” inquiry. I mentioned the social studies assignment and that Mandy Thomas had volunteered to be my partner.
Mom paused for a moment before asking me, “Doesn’t Mandy always ask to be your partner when these two-person assignments come up?”
I thought about that for a moment and said, “Come to think of it…yes. I think she’s been my partner the last four times we’ve had to work in pairs.”
“Doesn’t that tell you something, Danny?” she asked me.
“Yeah, because she’s a good student, she and I both dislike working with idiots whenever it can be avoided.”
Mom smiled at me and commented, “I think it might be more than that, Danny. She might be smitten with you.”
I had never considered that possibility. Actually, I had never considered any romantic possibility with any girls in my school. I guess I was a bit of a latecomer to discovering the charms of the fairer sex. I conceded that Mom could be right about Mandy. All of a sudden, I was flattered because Mandy was quite a friendly, pleasant girl whom I’d rank slightly above average in the looks department. She was also noticeably pubescent, as were three-quarters of the girls in Mr. Preston’s class.
“I suppose I could do a heck of a lot worse than Mandy Thomas,” I said to Mom. “She’s alright!”
Mom made a rather bold suggestion: I should ask Mandy why she always wanted to work with me on school assignments. If it was for more than just academic reasons, I should let her know that I was interested and available. I told Mom I’d do just that—if I could somehow muster the courage. I had never said anything remotely like that to a girl in all my 12 years.
Part Two
The next day at school, when Mandy and I were looking through a ream of statistics about the agricultural outputs of various South American countries for our project, I suddenly figured there was no time like the present to follow Mom’s advice.
“Mandy, excuse me for asking this question. Honestly, I don’t mind working with you at all, but why do you always want to work on school projects with me? If your answer involves something more than just getting a good mark, I’m both flattered and interested in getting to know you better.” I had practiced that line 20 times in my head before saying it to Mandy. I figured that was both as vague and specific as I wanted to be.
Mandy smiled and sweetly said, “Of course it’s more than schoolwork. I’m glad you finally caught on, Danny. I like you…a lot. So do about half a dozen other girls in this class. I want to get you as a boyfriend before they do.”
I was tempted to ask who the other girls were, but I figured that could be perceived by Mandy as an insult to her, so I kept my mouth shut on that topic. I did happily tell her that we should walk home together after school to discuss this boyfriend/girlfriend arrangement that she wanted. Frankly, I now wanted it, too.
My usual walk home from my elementary school was six blocks. Mandy only lived four blocks away, so I was a bit disappointed when we got to her house so quickly. During our trip we were constantly exchanging compliments. I told her how smart she was, how friendly she was, and finally how pretty she was. She said the same to me, except she referred to me as a “handsome hunk.” That was a new one to me. I loved hearing that, of course. Mandy invited me to come inside to watch TV for a while. In my part of the country, there were always excellent sitcom reruns from the 1960s for after-school viewing.
Mandy introduced me to her mother who seemed especially thrilled to meet me. “Mandy talks about you all the time, Danny!” she informed me.
“She does?” I said with a tone of disbelief.
“Mom, you’re embarrassing me!” Mandy complained. Her mother half-heartedly apologized for the comment and sent us to the family’s rec room with tall glasses of milk and oatmeal cookies as a snack. We sat on the couch. Mandy turned on the TV to the channel that was showing Bewitched.
“Oh, good!” I said. “It’s an episode with Dick York as Darrin.”
“Yeah, he was way better in that role than Dick Sargent,” Mandy agreed. Then she immediately sat on the couch beside me—so close that our hips were touching.
“Comfy now?” I asked facetiously.
“Absolutely!” she said as she wrapped her arms around me. I happily did the same thing with my arms—which elicited a slight coo of pleasure from my newfound girlfriend. Within two minutes, neither one of us cared about the sitcom on the screen. We were embracing each other tightly and planting kisses on each other’s face and neck. Things were certainly moving along swiftly in this nascent relationship!
About a minute later, we were interrupted by Jill, Mandy’s five-year-old sister who seemed fascinated that her older sibling was in the arms of a boy and enjoying it thoroughly. “Hi, I’m Jill,” she said while I was trying to kiss Mandy’s left earlobe.
I interrupted my romantic pursuit to say hello to Jill in return.
“Are you Mandy’s boyfriend?” she quickly asked. Before I could even nod a yes, Jill asked her sister, “Mandy, when did you get a boyfriend?”
“Today, Jill,” Mandy said impatiently. “Now leave us alone, please.”
“No, I want to watch Bewitched like we always do. It’s my favorite TV show.”
“You have good taste, Jill,” I told her. “It’s one of my favorite shows, too.” I gave her a playful tap on the nose with my finger. Jill smiled at me and giggled. To me, Jill was a novelty. I was an only child so I had no brothers or sisters at home to amuse or pester me.
Jill shouted at her mother who was in the kitchen. “Mom, Jill has a boyfriend now. Can I have one, too? It looks like having one is fun.” I chuckled at Jill’s observation, but Mandy turned about three shades of red inside of five seconds.
Mrs. Thomas laughed and replied, “If you can find a nice fellow like Danny for a boyfriend, it’s okay with me.”
Mrs. Thomas also reminded Mandy that she hadn’t brought in that day’s mail, which was apparently one of her daily chores. Mandy excused herself to do that simple task. As soon as she left the room, Jill, who must have misunderstood what her mother had told her, said, “My turn now!”
Jill assumed the spot on the couch where Mandy had been sitting, wrapped her arms around, leaned forward, and began kissing me just as Mandy had been doing!
This action took me totally by surprise. “Well, aren’t you a little sweetheart!” I said. I lifted her directly onto my lap and gave her a couple of benign kisses on her cheeks.
“I was right! This is fun!” exclaimed the affectionate five-year-old.
It didn’t take Mandy long to finish her chore, so she was back in the rec room inside of two minutes. When she saw Jill in the spot she had vacated, Mandy said, “What’s going on here?” with an annoyed tone in her voice.
“Jill was just taking your place until you got back,” I offered as an explanation. “She’s a real cutie—a junior version of you!”
Mandy, to her credit, knew I was just having a bit of goofy fun and entertaining Jill at the same time. “Okay, Jill, I’m back now. Danny is my boyfriend—not yours. You’ll have to find one your own age in kindergarten tomorrow.”
Jill was having none of that. “Danny, please come back tomorrow so we can do some more kissing. I liked it!”
“Maybe I’ll do that!” I informed her. In the meantime, let me give you three more kisses that will have to last you until then. I kissed Jill’s forehead and both cheeks as if she were my little sister, too. She then darted into the kitchen to tell her mom that she wanted to find a boyfriend “as nice as Danny is.”
“You have an unusual and very affectionate little sister, Mandy.” I said.
“Yeah, I refer to her as the nuisance,” Mandy stated. Then we resumed our cuddling. Mandy and I never did anything beyond that.
Part Three
I always got to school well in advance of the bell so I could spend time shooting the breeze with my friends about whatever was on our minds. That morning, I couldn’t wait to tell them about Mandy and our romantic encounter at her house. I saw three of my buddies huddled together about 50 yards away. I began to approach them when I was intercepted by a little tornado.
Jill Thomas had spotted me in the distance, sprinted towards me, and climbed aboard me with a flying leap. It was an impressive physical feat. i almost lost my balance. I instinctively wrapped my arms around Jill, and she squeezed me as tightly as she could. She amusingly told me, “I like hugging and kissing you better than any boy in kindergarten, Danny. I think you’re dreamy.”
That was an adjective I didn’t expect to hear from a five-year-old. I laughed and said, “So does your sister!” A moment later I added, “Jill, I guess it’s okay if you want to kiss me, too. I don’t mind! I guess I owe you a few.” I gave her a huge bear hug, told her she was adorable, and gave her three gentle kisses on the same places on her face where I had the previous afternoon. I set her down and she promptly ran off. I think Jill was going to brag to her little friends about her interaction with me. (I was sure of it later that morning when another kindergarten girl, whom I didn’t know, asked if she could kiss me, too! Thoroughly amused, I said, “Okay!” and kissed her in return. Quite content with her achievement, she scampered off. I never did find out her name.)
Over the next two months, every time I visited Mandy’s home, Jill simply bided her time. The moment Mandy stepped out of the room, Jill promptly draped herself over me. Of course, I didn’t do anything remotely sexual. After all, Jill was a very little girl. I just accepted her demonstrations of affection with amusement and a bit of wonder. After the third or fourth time, Mandy accepted Jill’s actions toward me as something that would be ongoing. Still, after a few minutes, Mandy would draw the line and say, “Enough is enough, Jill. Remember Danny is my boyfriend, not yours.” That remark seemed to suffice. Jill would set me free and then quietly leave the room.
For some reason which has been lost to the passage of time, Mandy and I slowly drifted apart. Within about five months we were no longer a couple, which was a bit of a shame. A few months after that, the Thomas family moved to another city. I thought I’d never see any of them again.
Part Four
Fifteen years later, when I was 27 and living in a different city from where I grew up, I was invited to a neighbor’s Christmas party in mid-December to sing carols and spread good cheer. Less than a minute after I walked through the front door, I was surprised to see a familiar face among the other party guests. For a moment, I thought for sure it was my former girlfriend, Mandy Thomas. This young woman did not look to be in her late twenties, though, so it couldn’t be the case. The mystery was solved when she approached me and cutely said, “I want a boyfriend, too, just like Mandy.”
Now I knew exactly who she was! “Good heavens!” I said with great surprise an delight. “You’re Jill Thomas, right? The last time I saw you was when you were five or six years old!” Jill certainly wasn’t that age any longer. She was now a very fetching, 20-year-old brunette with a curvaceous figure. If she wanted to sit on my lap and drape herself across my torso—as she often did 15 years earlier—I’d have no objections whatsoever!
“My, you grew up beautifully,” I couldn’t resist saying to her.
“You’re still dreamy, Danny,” she replied. I thanked her for the kind compliment.
We both discovered that neither of us was presently in a relationship, so our stay at the Christmas party was brief; we stayed for perhaps 15 minutes. We drove in separate cars to a nearby motel that had hourly room rentals. After I paid for a two-hour stay, we practically raced down the corridor to Room .
It was like turning back the clock—but much better. I sat on the end of the bed, and just like 1976, Jill promptly plopped herself on my lap and started kissing me. Unlike 1976, Jill had a much more interesting anatomy for me to enjoy and explore.
I immediately began caressing her sizable breasts. “You didn’t have these 15 years ago, Jill. That’s one improvement!” I noted between passionate kisses. Jill was also wearing a dress, so I was able to slip my right hand inside her panties and fondle her vagina. “Well, I suppose you had this in 1976, but I never touched it.”
Jill’s reply was, “Maybe you should have, Danny, because I like what you’re doing right now!”
About 30 seconds later we had both totally disrobed and were continuing our long kisses in the center of the bed. My hands were roaming in all directions, from Jill’s marvelous tits, to her inviting pussy, to her cute derriere. She was a fine example of youthful femininity, and I was going to enjoy all the treats that it provided.
Jill seemed to enjoy what I brought to the table. She was skillfully manipulating my penis with her right hand, bringing it to full erection in a matter of seconds.
Jill commented, “Mandy was a lucky girl to get fucked by this lovely dick all those years ago.”
I corrected that misconception in a hurry. I stated, “Mandy and I did a lot of hugging, kissing and perhaps a bit beyond that, but we never came anywhere close to doing this in the few months we were a couple.”
“That just means my sister was very stupid preteen girl!” Jill remarked. “Let me make up for that oversight.”
Jill immediately mounted me and gave me a wonderful cowgirl-style fucking, complete with hip gyrations and dirty talk. “Your dick feels wonderful in my pussy, Danny! Fire a big load of cum deep inside me. It would be so sexy. I can’t wait to brag to Mandy that I got what she didn’t!”
I obliged…but not right away. I enjoyed playing with Jill’s jiggly boobs while she rode me. Of course, inevitably, Jill’s sexy body had its effect on me. “Here it comes!” I warned her. Jill kept bouncing on me as I had a huge ejaculation. Jill came as well, which pleased me as much as it pleased her.
Since we had the room reserved for another 100 minutes, Jill and I cuddled, kissed, and learned about what had happened in each other’s lives over the past 15 years. Mandy, Jill told me, had gotten married at age 22, but she was divorced within a year because her husband was a serial philanderer. Her parents were doing well, but her father had a few heart issues. Jill herself, was enrolled in university, taking a general bachelor of arts program with no specific career goal in mind. I said I was gainfully employed by a publishing company as an editor and proofreader for several local magazines. My mother had died two years earlier from ovarian cancer, but my father was in fine health and was coping well as a 53-year-old widower.
“Now that we’re caught up, Jill, let’s have another fuck!” I suggested.
“Yes! What a great idea!” she agreed.
This time I assumed the assertive role in our intercourse. With my penis once again stiff and ready for more carnal action, I mounted Jill missionary-style and fucked her with great enthusiasm, driving my dick deep inside her vagina. Jill was a moaner—which turned me on. I aimed to please her, so I varied my thrusts, giving her short quick ones, long slow ones, and everything in between. Within ten minutes I had delivered another load of semen into Jill’s lovely, shaved pussy. Jill had a second orgasm, too.
I was ecstatic with my solid performance in bed, but I was also thoroughly exhausted. We both fell asleep in each other’s arms. We were rudely roused awake by a loud knock on our door. It was the motel’s desk clerk informing us that our two-hour rental was now done. I woke to find that my face was buried between Jill’s two lovely breasts. They had been excellent pillows for me.
Jill and I continued to get together for dates and sex with the latter being our favorite pastime. It was inevitable that Jill became pregnant. That didn’t bother me. On some level that was what I wanted to happen. Our wedding, a small civil ceremony, was held when Jill was three months into her pregnancy. We did have a fairly large reception afterwards, though.
To me, the most memorable part of the wedding feast occurred when, during a lull, Mandy marched up to where I was sitting with a cheeky and mischievous grin on her face. She suddenly threw her arms around me, and announced to everyone, “Mandy wants a boyfriend too, just like Jill!” Then she smothered my face and neck with kisses as if the calendar had gone back to 1976 all over again! The only thing missing was a Bewitched rerun on TV.
Jill thought her sister’s creative stunt was hilarious.
🔞 Candy.AI 🔥 AI Sex Chat – Roleplay, Erotic Stories, Try for Free 🕹️