Following Orders

High school senior Sammy has a marvelous chance to screw a classmate's gorgeous stepsister. Will he be able to cope with her overly demanding nature, though?

Part One

I, Sammy Thompson, was 18 years old in February 1985. I had just begun my last semester of high school. The day after my birthday, I received a great and unexpected gift from a classmate I barely knew. His name was Ken Miller. That morning, Ken intercepted me just before I was about to enter my homeroom for the daily attendance check and to hear the school’s standard morning announcements.

“Sammy, wait a minute! I need to speak with you for a moment or two, please!” he shouted at me just before I was about to walk through the doorway.

We were only acquaintances. I probably hadn’t spoken to Ken more than a handful of times since I first became aware of his existence in the ninth grade, but I was certainly willing to listen to whatever he intended to say to me. Therefore, I stopped, retreated a few steps from the doorway, and leaned against some nearby lockers to hear him out.

“This is going to sound strange to you,” Ken began, “but my stepsister Pauline has a message for you. This is it. I’m supposed to wait for your reply.” He handed me a white envelope with my name written on it.

I had no idea that Ken had a stepsister, and the name Pauline Miller was totally unfamiliar to me. Still, I was very curious to see her note. I opened it. It turned out there was more to it than just a missive. It read, “Dear Sammy: I recently saw you at the indoor pool at the community center. I asked around and found out what your name was. I also learned you attend my stepbrother’s high school and are the same age. I think you are very handsome and I really want to have a fuck with you! Enclosed is a photo of me. If you are interested in meeting up for sex, let Ken know and we can arrange for it to happen.”

I picked up the small photograph contained within the envelope and got an eyeful. Pauline was posed sexily on a couch without a stitch of clothing on! She was quite an attractive girl who clearly was of Asian ancestry. She had no resemblance whatsoever to her stepbrother—which, of course, made complete sense.

“Your stepsister is Asian?” I said in a questioning manner.

“Yes, that’s correct,” Ken responded. “My father’s job takes him all over the world. He met Pauline’s widowed mother during a business trip to Hong Kong. They hit it off and got married about a year ago. That meant I ended up with Pauline as a stepsister.”

“She’s not exactly shy, is she?” I noted.

Ken laughed at my comment. “No, Pauline is definitely not a shy girl. That photo doesn’t do her justice. She’s 16 years old, but she could pass for 20—and she’s very demanding. Pauline can be bossy sometimes; she certainly likes giving orders. She focuses on what she wants, and she always strives to get it. Pauline and her mom inherited a ton of money when her father died, so my stepsister spends her way to happiness. I was one of the first things she wanted, but she didn’t need to spend a dime to get me.”

I laughed at that last comment—and so did Ken. Then he continued, “Of course, now that we’re related by our parents’ marriage, we’re now off limits to each other sexually. Screwing her was fun while it lasted, though. I can honestly attest that Pauline is a fabulous sex partner. Now it looks like she wants you, Sammy. I’d say you’re a lucky fellow.”

Ken further explained that I’d never seen Pauline at our high school because she attended a very posh private school for girls. She signed up for swimming lessons at the same community center where I occasionally went for a dip with my buddies. (It had a large indoor pool, the only public one in my midsize suburban city.) Apparently, Pauline had seen me on the pool’s deck in my swimming trunks this past Saturday afternoon when the public swim was about to end and her lesson was about to begin. I assume she liked what she saw and impulsively decided I should share her bed. I was certainly flattered. I had always thought Asian girls were especially feminine and cute, so Pauline physically appealed to me, too. I had no steady girlfriend at the time, so it did not take me long to make a decision. Of course, I told Ken I was more than happy to accept Pauline’s offer of sex. Since nothing even remotely like this had ever happened to me in my life, I curiously asked, “Ken, what does Pauline see in me?”

Ken proffered a theory. “In the short time that I’ve known her, I’ve observed that Pauline is attracted to tall, young, lanky, white guys, like we are. She’s maybe 5’3”. She likes the way that males from this part of the world tower over her. I’m six feet tall and you are about two inches taller than I am. Pauline told me that she was attracted to me because of my height and the way I looked. I suppose I’m not a bad-looking guy, but you easily outshine me in the looks department, Sammy, so imagine what Pauline thinks of you!”

I didn’t have to imagine anything. The note and photo from Pauline made it abundantly clear! I gave Ken my phone number so Pauline could contact me. He noted, “Knowing my stepsister, she’ll call you about ten seconds after I give her your phone number, so rush home from school today and be close to your telephone.” That I did!

Part Two

I had been home for perhaps 10 or 12 minutes when I heard the telephone ring. I yelled upstairs at my mother not to answer it as I said it was likely for me. I was right. I picked up the downstairs extension. Pauline was on the line—just as I expected. She introduced herself as Pauline Chin, which puzzled me for a moment. Then I deduced she had retained her surname despite her mother remarrying. She got right to the point.

“Sammy,” she said excitedly, “I’m so happy you responded favorably to my note. The moment I saw you at the indoor swimming pool last Saturday afternoon, I knew I absolutely had to have a fuck with you! You really are a handsome young man! I want to ride your dick until you fill my pussy with cum!”

I thanked Pauline for the great, lusty compliment. It was a wonderful boost for my male ego. I told her I really liked what little I had seen of her—the sexy photograph—and her good looks were not to be underestimated. I also mentioned that I was getting aroused just thinking about bedding her sometime in the near future. Of course, I made sure I was well out of earshot of my mother during this conversation. She was a bit on the nosy side.

Pauline replied, “Thanks! I was hoping my photo would get that reaction from you, Sammy. I was going to wait for Saturday to meet up with you, but, on second thought, I think we should get together as soon as possible. Meet me in the lobby of the Empire Hotel tonight at 7 p.m.? I’ll book a room for us.” Ken had told me his stepsister could be pushy, and I definitely got the idea I was being commanded to show up rather than being asked. I normally balk at being ordered about, but in this case, I made an exception. Of course, I was happy to follow such a sexy directive!

Part Three

The Empire Hotel was known to be a swanky inn—easily the most luxurious in my hometown. In the past I had occasionally enjoyed quick sexual dalliances with high school girls, but they had occurred at bargain-rate motels. Thus, the Empire Hotel was definitely a step up in class for one of my trysts. Ken had said that his stepsister was very free about spending money. I figured this was just an example of that personal trait. I agreed to be at the appointed place at the appointed time.

When my mother asked me who was on the telephone, I gave her a half-truth. I said it was “the stepsister of a classmate who wanted to meet me for some reason.” I was not going to tell Mom, who was fairly liberal-minded, that I was going to head out that night for a guaranteed fuck with someone I had never met before. Mom kindly offered to lend me her car, but I said I’d just take the bus, which I often did. I did not mention my destination was a room at the Empire Hotel. Frankly, I hoped this date would turn out to be an all-night sexual adventure, so I didn’t want to leave Mom without her car until morning. I turned out to be prescient!

My bus trip took me to a stop directly in front of the hotel. I arrived at precisely 6:42 p.m., the exact time the bus schedule said I would. I had dressed fairly nicely, both for Pauline and for my surroundings. I had no intention of looking scruffy in such a high-end establishment. I didn’t have to wait for Pauline; she was already present, waiting anxiously in the lobby for me to arrive. We recognized each other at about the same time. We exchanged huge smiles. I noticed Pauline had made the effort to dress nicely, too. She looked great in her classy, short blue dress and nylon stockings. We embraced before either one of us said anything at all.

“Sammy, I thought the desk clerk might give me some trouble about renting a room here, but luckily there was none,” Pauline said, probably alluding to her young age. I agreed with her stepbrother: Pauline could have passed for 20, which probably fooled the clerk. She dangled the room key in front of my nose to emphasize her success.

On the elevator trip up to our sixth-floor room, Pauline said, “Sammy, let’s not waste any time at all. The second we are inside our room, let’s get undressed and get at it.” I noticed that Pauline was again issuing orders to me, but since I was totally in favor of what she was saying, I wasn’t about to complain. That’s exactly what we did.

I was the first to disrobe fully. Just the sight of Pauline in her undergarments got me highly aroused. I was sitting on a corner of the room’s large bed, sporting a tremendous stiffie that caught Pauline’s attention.

“Ooh! Stand up and let me get a good, long look at that hard dick of yours, Sammy. I think you have a magnificent penis.”

Again, I didn’t mind being bossed around under these circumstances, so I stood up and stepped closer to Pauline with my dick at full attention. She gave it a couple of playful strokes with each hand before she took off her panties and brassiere. She was a lovely sight to behold. Pauline was bustier than a typical Asian girl. That was a lovely bonus for me! I promptly took advantage of having Pauline’s goodies as playthings. I lifted her onto the bed—and easy feat for me as she seemed light as a feather. I immediately focused on her appealing chest, not wasting a moment before fondling and sucking on Pauline’s firm set.

I was about to give her a well-deserved titty fuck, but Pauline interrupted that fun sexual act to issue another one of her orders to me. “Fuck my pussy right this minute, Sammy! I don’t want to wait any longer for you to enter me! Do it now!”

I was a little bit miffed, but screwing Pauline’s vagina was one heck of a consolation prize! It was wonderfully tight—and it seemed to grab my penis and draw it in as far as it could possibly go inside her small but highly sexy frame. I lay sprawled on top of her, with my hands firmly on her waist so I could give her strong, passionate thrusts in rapid sequence. The feeling was fabulous! I didn’t want it to end anytime soon. Pauline seemed pleased by my efforts. She was squealing and moaning with delight. She wasn’t quiet about it. I suspected anyone occupying the neighboring room knew exactly what Pauline and I were doing on the other side of the wall.

I hadn’t had time to even consider wearing a condom for this sexual romp. Pauline didn’t seem to care about that at all. “Keep at it, Sammy!” she demanded. I did my best. After about eight minutes, I was about to explode. I had the most intense orgasm I had ever experienced in my life. I didn’t officially time it, but it must have lasted for 30 seconds—perhaps even longer. I felt drained, but what a magnificent feeling it was!

Despite the early hour—it wasn’t even 7:30 p.m.—I was about to fall blissfully asleep, but Pauline was having none of that. “Get hard again, Sammy!” she insisted. “I want to ride you.” It took about two minutes of Pauline lovingly handling my penis for me to at least return to a semihard state. Pauline pushed my shoulders to the mattress and, true to her words, mounted me, and gave me a vigorous riding. She was an energetic bedmate—there was certainly no doubting that. Pauline bounced and gyrated for 15 minutes until I managed a second ejaculation. It was nowhere near as impressive as the first one, but I was amazed I had it in me.

Surely, I thought we were done, but Pauline was still full of surprises and continued to call the shots. “We’ll do side-by-side screwing now, Sammy!” I figured I had no veto power, so I went along with her desire. I positioned myself on my side, with Pauline doing the same to the right of me. I fondled her breasts to try to get aroused one more time. It worked. The moment my penis stopped being totally flaccid, Pauline grabbed the shaft and placed it back inside her well-used vagina. It must have taken 30 minutes of gentle thrusting, but I attained a third ejaculation. Not long afterwards, my testicles began to ache from overuse. I had never experienced that uncomfortable sensation before. Then again, I had never been Pauline Chin’s sex partner before, either.

I desperately wanted to sleep, but I knew I had to telephone home. My worldly father answered the call. “I won’t be home tonight, Dad,” I told him. “There’s no need to worry about me, though. I’m totally okay. I’m in a room at the Empire Hotel screwing a beautiful girl from Hong Kong. Pauline—that’s her name—is unbelievably demanding, but I’m doing my best to satisfy her.”

“Ah, you poor boy!” Dad said with enormous sarcasm. “It must be a terrible ordeal for you! You might need trauma counseling.”

“I’m just thankful I’m 18 and I can handle the physical strain,” I told him. “She’d probably kill an old geezer like you.” Dad was 44 years old at the time. He just laughed at my remark and wished me well. The phone call ended with him saying, “Now get back to work, you sluggard!”

Pauline patted the bed to indicate where I should return without further delay. “I’m a bit tired,” she informed me. She was still giving orders, though. She declared, “Let’s just go to sleep in each other’s arms for now. Perhaps we’ll do more fucking in a few hours.” I fully agreed. I was about to fall asleep on my feet. Sleeping in this comfy bed with beautiful Pauline draped over me sounded a whole lot better.

I dropped off immediately and slept soundly. The room’s clock radio read 3:50 a.m. when I woke from my slumber. Pauline, still clinging to me, was a sexy sight. Remarkably, I was getting sexually aroused again. This time I decided to take charge while Pauline was asleep and could not make demands of me. I rolled her onto her back, straddled her, and finally got my delayed titty fuck. Pauline woke to find my stiff rod sliding between her breasts. Her response was to giggle softly. I could tell she was about to suggest something, but I put my hand over her mouth to stop her from speaking.

“Oh, no! No more orders from you for the rest of the night, Pauline!” I told her. "This one is for me, honey.” When I felt one more stirring rising in my balls, I placed the head of my penis in her mouth and came a fourth time. It was barely a few dribbles of watery semen. Pauline diligently gulped it down with enthusiasm. She was quite a girl. Doing what I wanted to do for a change of pace felt quite liberating. We both went back to sleep, waking slightly after 8 a.m. Our eyes opened almost simultaneously.

Neither one of us felt like going to our respective schools that Tuesday morning. We had the hotel room reserved until 11 a.m.—and we stayed until 10:59. Pauline ordered room-service breakfasts for us: Two orders of bacon and eggs. (She didn’t ask me what I wanted. Totally in character, she just ordered a second serving of what she was having and assumed I would like it, too. This girl apparently lived to be in charge!) We cuddled quite a bit and kissed romantically. We hadn’t done much of either before midnight. Our final sexual encounter that morning was a refreshing shower for two. I don’t know how, but I managed to attain an erection while the warm water cascaded over the two of us. There was no way I was going to ejaculate, though. I had reached my physical limit. My balls were empty.

As we rode the elevator down to the lobby, Pauline said, “You were an excellent sex partner, Sammy! You were even better than I had imagined. I hope you were pleased with me, too. Come back here Saturday night at 7 o’clock for some more sex. When we get to the lobby, I’ll book this same room again, if I can.”

“That sounds more like a command than a request, Pauline. You can’t help yourself, I guess, but you are ordering me about again!” I informed her.

Pauline frowned for a second or two until I sweetly said to her, “Hey, I love it when you do that.”