Nikki's Challenge

Nikki's father jokingly suggests her beloved tutor Tony might be incapable of sex because he's sixtyish, so 14-year-old Nikki decides to find out for herself.

Part One

Nicole (Nikki) Feldman had been one of my tutoring clients for six years—which is a long run in my business. At the time of this story, she was 14 years old and was easily in the top ten of my favorite students ever. That’s actually quite a lofty ranking because I was 61 at the time and I’d been a professional tutor since I was 25. Therefore, I had dealt with several hundred students over the course of my lifetime. My name is Tony Romanelli, and I was and still am a lifelong bachelor.

I think it was fair to say that Nikki was an average student. She was always good natured and willing to learn. Nikki possessed the correct attitude about our sessions. She looked upon my one-on-one services as a chance to improve her school performance. Nikki was a talkative girl, an only child who was always asking me questions, both about her schoolwork and topics far beyond it. Over the years when I had visited her home, I had fielded her queries about everything from the existence of Santa Claus and space aliens to why people and animals in the southern hemisphere don’t fall off the planet.

I was surprised to discover via her anecdotes that Nikki was a promiscuous girl, even as a preteen. When her parents were out of earshot, she’d tell me about her frequent kissing and groping sessions with some of the boys in her sixth-grade class. (There was nothing wrong with the eyesight of those boys. Nikki was a very attractive, short-haired brunette who was probably slightly ahead of her female classmates when it came to physical maturity.) When I cautioned Nikki that such discussions with me might not be appropriate, she promptly questioned why that was the case. I struggled to find a passable answer; I couldn’t possibly tell her the truth—that they were getting me aroused! Therefore, I just replied, “Okay, my dear, I suppose we’ve known each other for so long that we have no taboo topics between us.” Nikki just smiled and affectionately squeezed my left hand with her right hand. She really was a sweet and charming young girl.

Part Two

Over the years, my usual tutoring time with Nikki was Tuesdays from 7 to 8 p.m., with special, occasional sessions on Saturday mornings if she needed help beyond an hour per week. It was on such a Saturday in May when I arrived just before 10 a.m. to help Nicole with some English assignments that were giving her difficulty. She always had difficulty with the mechanics of English, such as good grammar and the wonderful literary devices such as similes, personification and hyperbole that make the language come alive.

I noticed something was unusual when I parked on the street in front of Nikki’s home: The Feldmans’ driveway was completely vacant. There was normally at least one car parked there, if not two. I rang the doorbell. As soon as Nikki opened the door, I pointed at the carless driveway and asked her where her parents were that morning.

“Dad is involved in a charity golf tournament today—even though he’s not much of a golfer,” she informed me. “He had to borrow a set of clubs from a neighbor. Mom is attending some sort of social event with her sister who lives 40 miles away. They’ve both been gone since early morning, and I expect they won’t be back until well after sunset tonight. I’ve got plenty of leftovers in the fridge to eat—and money to order a Chinese food delivery if I feel like doing that, so I’m all set for my meals for the whole day.”

I nodded and noted, “In all the years that I’ve been coming here, Nikki, this is definitely the first time that at least one of your parents hasn’t been present in the house. It feels strange to be here alone with you for tutoring. It’s quite pleasant, of course, but it’s still a trifle odd to me.”

Over the course of my tutoring career, I’ve encountered all sorts of parents who saw me in ways that differed greatly. I’ve experienced every extreme. Some mothers and fathers have perceived me as a welcome friend who posed no threat whatsoever to their child or children. Others took a more cautious outlook, always remaining in the house while I was there, sometimes nearby, other times not so close. I’ve had a few parents who actually sat in on every session and heard and saw every interaction I had with their children. They were absolutely welcome to do that; I had nothing to hide. I’ve also had the full gamut of student behavior, from those displaying open hostility toward me—those kids never remain my tutees very long—to those who were extremely friendly to the point of being very affectionate. I found that to be the case often if I was tutoring a pupil in a household where there was no adult male regularly present. I’ve often figured someone could write an interesting sociology essay about the variances in students’ behavior with their tutors. Nikki was always friendly with me since Day One, but nothing beyond that—until today.

“Yes, it is unusual, Tony,” Nikki said to me, “and it wasn’t supposed to be that way. Mom had planned her trip with my aunt a few months back. Dad signed up to play in the golf tournament only about two weeks ago. They each had not told the other about their respective plans, so when I asked them if you could come here on Saturday to assist me with an assignment, they both agreed, each not realizing that the other wouldn’t be present—until about two days ago. Mom was going to call you to cancel today’s session, but I really do need your help in writing a memoir. Dad told her and me not to cancel. Do you want to know his reasoning?”

“Sure,” I said without reservation.

Nikki took a deep breath and said, “You might not like this, Tony, but Dad said that since you were now in your sixties you were completely harmless and presented no threat to my safety. He literally said, ‘Nikki will be absolutely safe on Saturday morning. At his age, I don’t think Tony could molest her even if he wanted to. He must be 60. He probably can’t get it up anymore.’ Mom laughed at what Dad said, but I thought it was a cruel remark to make.”

Very few times in my tutoring career have I been dumbfounded. This was certainly one of them, however. I was miffed on several levels, especially about my virility declining. I finally said to Nikki, “That is a bit of a low blow—and it’s inaccurate, too. I might not be 18 anymore, but my equipment is still in working order.”

“I think you should proceed to prove them wrong,” Nikki suggested. “Once we’re finished with the hour of tutoring, I think you ought to give me a good fuck, Tony, to show you can still get it up. Hey, I’ve always wanted to be intimate with you, anyway.”

I was dumbfounded for the second time within two minutes. I eventually asked, “You have, Nikki?”

“Of course,” was how she responded. “Haven’t you picked up on my signals over the years? I guess some guys don’t get the hint and just have to be told outright. Anyway, do you have any commitments after our tutoring ends at 11 a.m.?”

“Well, I had tentatively planned on getting my tires rotated at my friend’s garage, but I can have that done anytime. That was the only thing on my agenda after tutoring, so yeah, I have no firm plans, Nikki.”
“Forget about firm plans,” she joked. “I want to prove you can still have a firm penis despite your age. Don’t worry about your tires being adjusted, let me adjust your dick!”

I laughed and noted, “For someone who supposedly has trouble with literary devices, you often create clever puns, Nikki!”

Thus, it was agreed that after an hour of tutoring, I’d stick around for Nikki’s challenge and do something I’d never come close to doing before: screwing a student of mine.

Part Three

Nikki’s homework consisted of penning a memoir. That required me to teach her the difference between autobiographies, biographies, anecdotes and memoirs. I told Nikki to think of some memorable incident in her life that she could write at least 300 words about. It didn’t have to be anything life-altering, I stressed, just something from her past that she could easily recall.

“How about my first sexual experience, back when I was 11? Will that do?” she asked me. I almost gagged on the ice water I was drinking. I said that was probably a bit risqué for a middle-school English assignment, but I said that reminiscing about a first kiss might work out nicely.

“Okay,” she agreed. “My first kiss preceded my first fuck by about ten minutes, so it’s basically the same story with a different ending.” I then knew for certain that I was going to have a great time screwing Nikki once our hour of tutoring ended!

Nikki relayed the story to me while I jotted down a few notes. According to her sexy tale, she was smitten by one of the male counselors-in-training at a summer camp she was attending. Nikki was indeed 11 and the boy was 14. She instigated the romp. The lucky boy, initially shy, quickly got into the spirit of the occasion. Nikki’s written version of the story ended with a romantic kiss, but she regaled me with all the lascivious details that weren’t going to appear in her English paper. I admit I quite enjoyed them! I helped her craft the story into a solid narrative. By coincidence, we had completed Nikki’s homework assignment in almost exactly 60 minutes. The time had arrived for some carnal fun!

As Nikki began to unbutton her pretty yellow blouse, she asked me, “How old are you, Tony?”

I answered her honestly, “I’m presently 61 years old. I’ll be 62 on July 28.”

“Oh, Dad was right; you are in your sixties,” Nikki commented. “I’m a bit surprised to learn that. I would have figured you to be about 55. My guess would have been way off.”

“Thanks for the compliment, Nikki. People often underestimate my age,” I told her. “I guess that’s because I have very few gray hairs on my head.”

“I’ve never had sex with anyone over 17 before, Tony. Can you believe that?” Nikki asked me in a rhetorical way. I didn’t think I was supposed to answer her, but I did.

“Hey, I can certainly believe it!” I said strongly. “I might be totally wrong about this, but back when I was a teenager, girls weren’t nearly as promiscuous as they are today. Even if they were, girls still enrolled in middle school weren’t generally sleeping around with guys in their twenties and thirties.”

Nikki did not comment on my response. She just smiled warmly and said, “I think I’m going to enjoy having sex with you, Tony. I always like sex, but because of your age, you’re probably very experienced about such things. I think you’ll be a really great sex partner for me!”

I didn’t have the heart to tell Nikki that, given the way this conversation had unfolded, she might have had more sex partners than I had in my much longer life. I just replied, “Thanks for your confidence in me. I’ll aim to please and do my best.”

I then began to disrobe, too. By the time I was down to my shorts and undershirt, Nikki was standing a few feet away from me—spectacularly nude. The sight of her that way inspired me to pick up the pace. Within seconds, I was nude, too.

“Let’s just go over to the brown leather couch in the living room. It’s big and comfy. We don’t need a bed for fucking,” she told me. She took me by the hand and led me to it.

My mind briefly wandered into the past. I figured it had been about 40 years since I had ridden a girl anywhere near Nikki’s age, the last one being Dorothy Calhoun who lived about four houses up the street from me in my old neighborhood. She was one of those promiscuous girls I had told Nikki were so rare in my youth. One day Dorothy approached me out of the blue, said I was handsome, and accordingly wanted to give me a good fucking. Dorothy was rather attractive, so what male would say no to that offer? I hoped I could sexually please Nikki as I had Dorothy four decades earlier. Nikki’s Dad’s harsh words, though intended as a joke, had me silently questioning my carnal capabilities—something worrisome that had never entered my mind before this day.

Nikki took a relaxing position on the couch, lying in a manner that showcased her pussy. I could tell she shaved it regularly. (In contrast, Dorothy Calhoun’s vagina had been very hairy!)

“I just have to begin by licking that body part!” I enthusiastically stated.

“That’s definitely what I was hoping for!” Nikki confirmed.

While Nikki’s pussy was certainly desirable for cunnilingus, I was hoping this sex act would also buy me some time. I did have an erection, but I sensed it wasn’t as impressive as it usually was. I suddenly feared that maybe Mr. Feldman had been correct! I wanted my penis to be rock hard by the time I penetrated my sexy, young pupil.

I placed my head between Nikki’s thighs and began orally stimulating her most private part. “You know what you’re doing, Tony! That’s for sure!” she assured me. Nikki silently emphasized I was doing a passable job with my long licks by pressing down on the back of my head so I wouldn’t stop. She needn’t have worried about that. Nikki’s cunt was lovely. I’d have been quite content to lick and play with it all day. When I started to insert the tip of my tongue inside of her, Nikki became especially wet.

I was pleased with my performance so far, but I still wasn’t quite satisfied with my erection’s size and firmness. Nikki and I switched places on the couch. She began to give my penis a superb series of licks, sucks and blows that made it seemingly grow another inch.

“Fantastic!” I told her. “I suspect you’ve done this before.”

“Dozens of times,” Nikki admitted. “Just don’t tell my parents. They think I’m one of those wholesome virgins from the pages of literature.”

Within two minutes I had gone from wondering where I could be sufficiently aroused to prove I could still “get it up” to being worried about a premature ejaculation. Nikki’s oral skills were that good. I told her I wanted to ram her pussy doggie-style, which she thought was an excellent suggestion. She repositioned herself accordingly on the leather couch with her cute butt slightly in an elevated position. (I could tell she had done this before, too!)

I quickly stood behind her, placed my stiff rod where it needed to go and began strongly thrusting my manhood inside this teenage cutie. I kept up a swift pace, stopping only occasionally to feel Nikki’s firm breasts. At first, I thought they were nothing spectacular, but 14-year-old girls’ tits aren’t just desirable objects for teen boys. Every red-blooded male ought to enjoy them occasionally. (I have a neighbor my age who goes on vacations every year to far-flung places where he can easily pick up young hookers quite cheaply. He swears such sexual encounters keep him young! Over the years I had forgotten why.)

For the sake of variety, Niki asked my permission for her to mount me. What a silly request! Of course, my reply was a quick yes! Nikki rode my fully aroused penis with the skill and confidence of someone twice her age.

“This usually puts my sex partners over the edge, Tony! I’m surprised you haven’t come yet.”

“That’s one of the benefits of being 61,” I told her. “As the years pass, you learn over time to control and delay your cum shots.” (Of course, that was because it took far longer to get my equipment ready to launch a load of semen than when I was 30 or 40, but I didn’t divulge that truth to Nikki.) “Anyway, I want to finish with a good, old-fashioned missionary fuck, so I can proudly stare you in the face when I ejaculate.” I added.

Nikki also was quite agreeable to that type of climax. She really was a sweetheart. I thanked my lucky stars to have been aligned in a position that morning for me to give Nikki such a thorough screwing!

I really did intend to move directly into the missionary position and continue my penetrations, but I was distracted by Nikki’s breasts. Upon closer inspection, they were terrific. They weren’t too big and they weren’t too small. They fit her medium-sized frame perfectly. She had the type of boobs that narrow at the front to where the areolas come to a point, highlighting the nipples. They certainly invited male attention. They basically said, “Please fondle and suck these.” So I did. They were thoroughly enjoyable. I said to my bedmate, “Nikki, when you have babies, if you don’t breastfeed them, it would almost be criminal to deprive them of that pleasure. They are your best features, for sure.” Nikki was so flattered by my compliment that she gave me a long romantic kiss—which I liked—except that it cut into my valuable tit-sucking time.

After that carnal desire of mine was sufficiently sated, I finally did what I promised to do: finish Nikki off, in a matter of speaking, with a thorough face-to-face fuck. I slid my dick into her for the third time. It seemed like it was tailor-made to fit there. I immediately started copulating to a rhythm. I got a bit silly and broke into an upbeat singsong to match it: “Let’s make a baby, Nikki! Let’s make a baby!”

“I don’t think so, Tony! I don’t think so!” she countered musically herself. She stopped long enough to say, “Tony, this fucking session is plenty of fun. It’s been great to prove my father wrong about you. But it’s not about making me pregnant. When you ejaculate, please pull out first!”

“Aw!” I said with fake disappointment. “I wanted to make 20 babies with you, Nikki. With that sexy body of yours, it would be easy for me to give you a strong blast of cum—even when I’m in my eighties. Okay, have it your way. Anyway, I want you to get a good look at my cum shot to see for yourself that I’m still a virile man despite my age.”

That key moment came about a minute later. Ever since I was 13, my testicles always produced stronger than average ejaculations. I already knew this one would not disappoint me. I pulled out and fired a vast load all over Nikki from her navel to her neck. It was comprised of three long, wonderful ejaculations. We both said nothing for a while. I finally broke the silence by noting, “He’d likely kill me for it, but I wish your father could see you covered in my hot goo! Who says I can’t get it up at age 61?”

“Can you stay, Tony?” Nikki asked me sweetly.

I had to face reality and share it with this adorable girl. “Nikki, I’d love to stay and fuck you four or five more times, but I’m not 18 or 25 or even 40. I’ll need a couple of days at least to recover from that whopper of a cum shot. It was fabulous, but I’m completely physically drained!”

Nikki giggled and said, “That’s not what I meant, Tony! I’m inviting you to stay for lunch—not more sex! How does Chinese food for two sound to you?”