Colleen's Proctor

Sammy the tutor is already bedding an 18-year-old client. When her classmate also wants tutoring and offers sex as partial payment, of course Sammy agrees!

Part One

I, Sammy Clarkson, had been a private tutor for about a decade. It was June of 2021 and I was 31. I was tutoring a very attractive, 18-year-old girl of Sri Lankan ancestry named Fatima D’Souza. She had been my twice-a-week pupil since she was 14 and in the eighth grade. Four years later, she had also become my twice-a-week bedmate. This wasn’t a situation where a dirty old man was exploiting a teenage girl. It honestly happened purely by mutual attraction over time, but the two of us both seemed to really enjoy how things turned out.

Fatima needed my assistance to get her remaining history and English credits so she could graduate high school on schedule. To be helpful, I’d often extend her tutoring sessions at no extra charge. One cold night in January, I stayed an extra 90 minutes at her home to get Fatima caught up on a history unit in which she had fallen considerably behind. When Fatima realized we had actually done enough work to put her ahead of schedule, she was so delighted and grateful that she impulsively plopped herself on my lap and kissed me. I thoroughly enjoyed the gesture and wasn’t in any hurry to have our wonderful kiss end.

Our lips must have locked for at least two minutes—perhaps three—before Fatima returned to her chair giggling like a 12-year-old girl. Our passionate buss was a little on the risky side because both her parents were inside the house viewing a movie on Netflix. Luckily, they were watching it far from the dining room where their shapely daughter’s tutoring sessions were always held. (They would certainly not have approved.) Nevertheless, it was Fatima, not I, who suggested that we promptly adjourn that night’s long tutoring session and drive in separate vehicles to a nearby motel—one that was famous locally for its hourly rates. I smiled and quickly agreed. I shouted goodbye to Fatima’s parents and left in my car. Five minutes later, Fatima made some excuse to leave the house, too. I checked into Room #16 at the Open Road Motel with Fatima expected to join me at any moment.

When I saw her arrive, I opened the door to my room and waved her inside. She was so eager to begin on that first night that she sprinted about 40 yards to jump into my arms. For the next hour, we enjoyed ourselves thoroughly. Fatima was a well-built specimen of exotic femininity and I especially liked fondling her comely breasts. There was nothing romantic about our sexual intercourse. We both fully understood it was just lust in its purest form.

Fatima was quite good at getting me aroused. Without fail, she always brought me to an orgasm twice in every 60-minute screwing session we had. My main task (aside from pleasing Fatima with my erect penis, curious hands, and probing tongue) was to avoid ejaculating in her vagina for obvious reasons. Therefore, I often got creative with my cum shots, firing them on her tummy, on her face, in her mouth, and occasionally on her back if she was in a kneeling position. Once, purely by accident, most of a wild cum shot ended up in Fatima’s hair and inside her left ear! Be that as it may, I liked the variety of it all. With few exceptions, these sleazy motel romps became a twice-weekly ritual for Fatima and me.

One night, after Fatima was washing up in the bathroom after I’d launched three ropes of hot goo across her perky tits, she asked me about possibly tutoring a classmate of hers. This girl’s name was Colleen Harrington. I had never heard Fatima mention her before that moment.

“Colleen is taking an online English course because she couldn’t fit a traditional class into her schedule this semester, ” Fatima explained to me. “She has a final exam coming up and I know she could use some help.” Before we left the motel, Fatima phoned Colleen, who indeed verified that she was looking for extra help in English literature. Just to be playful, I wrapped my arms around Fatima and caressed her beautiful breasts while she spoke to her friend. Fatima tried to hand me her phone, but since my hands were occupied, she just held it beside my cheek. I cheerfully arranged to meet Colleen at a coffee shop at 4 p.m. the next day to discuss how I could help her.

“This is very nice of you, Sammy,” Fatima told me.

“If Colleen needs tutoring, I’ll be happy to accommodate her. I’m always looking for new clients,” I explained with a shrug.

“I know that!” Fatima interjected. “Sammy, you misunderstood me. I meant it was nice the way you caressed my boobs while I was talking on the phone. You do that so well, Sammy! You have a great, sensuous touch.”

I thanked Fatima for the compliment and continued groping her until our hour at the motel expired.

Part Two

The following day, a Friday, I met Colleen as scheduled at the coffee shop. I was told by Fatima that her school chum was about 5’7” tall and had straight, black hair that stopped just above her shoulders. She found me before I found her.

“You’re Sammy, right?” she asked me.

I agreed that I was Sammy Clarkson and always had been. She laughed at my little joke. I treated Colleen to a large hot chocolate as she was not the passionate coffee drinker I was. She found us a secluded table far away from anyone else in the restaurant. Without much small talk beforehand, Colleen quickly got down to business.

“I gather that Fatima told you I need some help with an online English course,” Colleen began. “It’s a literature course that primarily deals with short stories. I’m doing okay in it; my average is around 70 percent. However, there is one last major assignment. It a three-hour final exam that we do online at a time I can choose. It’s worth 40 percent of the entire course mark, so I have to make sure I pass it. Anything beyond that is a bonus.”

Colleen said she had slotted her exam for a Friday afternoon time slot one week from that very day, from 1 to 4 p.m. “I have to go to a specific website belonging to this online learning company and enter a code word sometime between 12 and 12:59 p.m. Then I’ll have access to the online exam. The rules are quite strict: Once I start the exam, I can’t stop until I am ready to submit it. In other words, if I leave the website, I won’t be able to return to it. Frankly, Sammy, the mere thought of a three-hour English exam frightens me.”

I asked, “Do you know what is on the exam, Colleen? Is it material you’ve already studied in class or is it material that will be completely fresh to you?”

“All we’ve been told is that we will be answering questions about the plot, literary devices, and vocabulary of two short stories we haven’t yet scene. That’s the scary part to me. How can I study for an exam about stories that we’ll see for the first time once the exam starts?”

“That’s not really uncommon for an English lit exam, ” I explained to Colleen in an attempt to comfort her. “Because it is new material, I suspect the two stories you’ll be reading ought to be quite straightforward. Anyway, you can prepare in advance by reviewing literary devices, and maybe do some vocabulary drills. That can’t hurt. I can certainly assist you with those, Colleen.”

Colleen still looked worried, but said, “Okay, let’s find some time in your schedule to do a few vocabulary lessons and review literary devices. Then, next Friday when I write the exam, I want you sitting right beside me at my kitchen table to assist me as much as possible.”

What Colleen was asking me to do—coach her during a timed exam—was wholly unethical. In fact, I looked at the posted rules for the exam. They said she needed a proctor present to attest that she wasn’t cheating in any way. I informed her about this. “I will be your proctor, if you like, Colleen, but this exam is supposed to be on the level. You are supposed to write it—not me.”

“Maybe I can make it worth your while, ” Colleen suggested. “How’s this: I’ll pay your usual hourly fee—I understand it’s $30 per hour—for the lessons leading up to the exam and the proctoring fee too at the same rate. To have you help me with the questions, I’ll happily fuck you like Fatima does.”

That was a startling statement for me to hear! I had perhaps naively assumed that Fatima would have kept our regular trysts a secret from her friends. That was obviously not the case. I said nothing for a moment and then shyly admitted, “Oh, so you know about what your sexy friend and I do after our tutoring sessions.”

“Yes, I do,” Colleen confirmed without much emotion. “Fatima says you are an enthusiastic fucker who can sometimes get a bit rough in bed, but the pleasure you give her is well worth it, overall. She often tells me she’d fuck you night and day for a week if she could.”

“Well, that’s kind of Fatima to say that about me. She’s great in bed herself—especially for an 18-year-old. She’ll fuck in any and all positions. I’d say she’s as eager to screw as I am. Her pussy is fabulous. It just seems to grab my dick and bring it to life over and over again even after I’ve come.” I suddenly stopped my sexual remembrances and said, “Perhaps I’ve given you too much information.”

“It’s basically nothing she hasn’t already told me,” Colleen said with a grin. “Believe me, Fatima knows she has a first-rate vagina to please males. Anyway, how about three hours of you feeding me answers to the English exam, followed immediately by three hours of fucking at that motel where you and Fatima are regular clients?”

Before giving her an answer, I studied Colleen’s anatomy in great detail. She had a reasonably pretty face. She was marginally taller than most high school girls, and could be described as lithe. She wasn’t as busty as the voluptuous Fatima, but what Colleen possessed on her torso was pleasant enough to please me. My father had a saying that I tended to agree with regarding women’s breasts. He’d tell me, “Son, anything larger than a mouthful is a luxury.” I could easily picture myself spending a lovely and blissful three hours fucking this girl in the same fashion I screwed her lusty and busty friend. Without any real explanation, I simply said, “Okay, it’s a deal, Colleen.” I shook her hand in a businesslike fashion. We then booked times for vocabulary lessons and a full review of literary devices. I told her I would make the reservation for the motel room once I got home. I was certain the front-desk manager would be surprised to see me there on a Friday. Like clockwork, Fatima and I always arrived on Sundays and Wednesdays to do our fucking.

Those two nights of regular lessons were quite fun, as they played to my strengths as a tutor. In my high school career and earlier, most of my English teachers were outstanding in providing me with excellent examples of words to learn and concepts to understand. They had stuck in my mind. I brought a few textbooks that I owned and quizzed Colleen from them. I noticed she was weak on some homophones. For example, she knew the word “rain” but not “rein” or “reign”. She also had trouble differentiating between a simile and a metaphor. Nevertheless, when Friday arrived, I figured Colleen was as prepared as possible for her English exam. Of course, Colleen looked quite relaxed, knowing that I’d be responsible for providing her with the answers whenever she faltered.

I signed in as Colleen’s official proctor at 10 a.m. when I was allowed to do so. Two hours later I drove to Colleen’s house, which was located about a dozen blocks eastward from mine. I got there just as Colleen was signing in to the course’s website. We greeted each other and got some pencils and lined paper ready. I had also brought along, in case we needed it, an old-fashioned paper dictionary. It was something that Collleen had never used in her life. That made me feel old.

The exam proved to be a cinch for me as I was very familiar with the two short stories on it. One was a slightly dark Roald Dahl tale called “Dip in the Pool” while the other’s title was “The Verger” by Somerset Maugham. Both stories had endings with unexpected twists. The first story was about a man who bankrupts himself buying chances in a pool pertaining to when his trans-Atlantic ship will arrive in New York City. Colleen didn’t understand the ending at all. Thus, she needed plenty of coaching with it. Colleen had a better grasp of Maugham’s story. It was about a longtime church official who is dismissed because his new boss discovered he is illiterate. My tutee was able to proceed pretty much on her own with that one. Colleen also surprised herself by zipping through the questions about vocabulary and literary devices also better than she had expected. My tutoring earlier in the week had clearly helped.

Colleen finished the exam with almost an hour to spare. I advised her to use the extra time to go over everything she had typed into her computer in the answer boxes. I helped her spot a couple of typos and other errors, so it was time well spent. Colleen clicked the save option for a final time and then the send button.

The time was exactly 3:48 p.m. Colleen did not have a car, so I drove us to the motel where I had booked a room for 4:30. She left a note on the kitchen table, reporting that the exam had gone well, but she lied to her parents in saying she had gone somewhere to celebrate with Fatima instead of stating the truth: She had actually gone to a motel to fuck her tutor and proctor for three hours.

Colleen was all businesslike when we got to our motel room. Her coolness was not a good thing. I tried to be romantic with her—more so than I ever was with Fatima—but I could tell by her body language and facial expressions that she was there merely to provide a promised service to me rather than enjoy the upcoming sexual fun and intimacy.

We both disrobed. I got into bed before Colleen did. As she stood before me in her birthday suit—a sight that was quite appealing—she noted this was just the third time she was going to have sex in her young life. The previous two intimate encounters were meaningless flings with male classmates just to satisfy her curiosity. The last one had occurred two years earlier. They held no fond memories for Colleen whatsoever.

“Maybe I can impress you more than your other two lovers,” I suggested. “Come here beside me and let me try. You might just enjoy it. I know I will.”

Colleen obliged and entered the bed from its left side. I immediately embraced her and began sucking on one breast while fondling the other. I playfully licked her nipples until they both grew hard. Slowly I could sense Colleen’s attitude begin to change. She was starting to enjoy the experience!

I put my face on her hairy vagina and started to stimulate that tender part of Colleen’s anatomy with my tongue. She started to squirm slightly and coo softly. When I tried to pull away, she said, “Sammy, can you continue with that for a while longer. I was enjoying it!”

“Of course, my dear!” I enthusiastically replied. “I want you to enjoy yourself!” The licking and sucking continued. I became bold enough to stick the middle finger of my right hand inside her pussy while I merrily licked all around it. Colleen became very wet in a hurry. This turned me on just as fast. I was wielding a mighty erection and I wanted to put it to use, so I ceased with the cunnilingus and mounted my 18-year-old lover in a missionary position. My hard dick slit into her love channel quite nicely.

“Oh, that feels terrific, Sammy! Fuck me as long as you like. I took a pill. I can’t get pregnant.”

“Whatever you say, my dear!” I replied. I attempted to please Colleen with slow penetrations followed by a series of quick, fast ones. It was marvelous!

I began to become very enthusiastic and aggressive as I rode her. “Do you like my hard dick, Colleen? Do you?” I asked rhetorically. “I want to fuck your pussy forever!” Colleen answered with moans instead of words. I could feel an ejaculation was imminent—and, from experience, I knew it would be a strong one. I gave one final, strong thrust and kept my penis deep inside her vagina as I let loose.

There was extreme pleasure running through me as I deposited three or four ropes of semen inside my bedmate, after which we embraced silently for about two full minutes. I glanced at the clock on the wall and commented. “Oh, what a shame we only have the room for another two hours and 45 minutes, Colleen!” That quip caused Colleen to laugh. I rewarded her positive change of attitude with several more thrusts to drain my penis of every last drop of hot jism.

It was great to witness Colleen change from an uninterested, passive lover to a fuck friend who was suddenly enjoying being intimate with me. She also had the same gift as her friend, Fatima—the ability to rejuvenate me quickly. Perhaps it was a personal trait they shared—or maybe it was because both of them were nubile 18-year-olds whose pussies were greatly desired by this 31-year-old man. Whatever the case, Colleen and I wasted very little time in resuming our lovemaking. This time Colleen mounted me as I laid happily on my back. She caught on to the “cowgirl position” quite quickly—obviously never having ridden her two previous lovers in such a way. “Hey this is fun!” she announced as she joyfully bounced on my reinvigorated penis and swiveled her hips. I busied myself by playing with her hard nipples. By the time the clock showed that 30 minutes had elapsed since we’d arrived, I had come again. It was not quite as powerful a blast as my first cum shot had been—that would have been incredible—but it still felt almost as terrific. AS I let out a sigh, Colleen fell forward with my rod still impaled inside her. She was obviously enjoying the late afternoon as we romantically kissed for several minutes.

“Having fun yet?” I asked her playfully.

Colleen answered my question with one of her own: “Is there any doubt at all about that?” she said. “Sammy, let’s try for orgasm number three...then four...then five...and so on!”

I felt the need to remind Colleen that I was a typical 31-year-old male and not a fucking machine, but I insisted I would try my very best to fuck her brains out for the next 2½ hours. She kissed me sweetly on the forehead and noted, “That’s all I can hope for.”

Indeed, for the next 150 minutes, Colleen and I experimented with all sorts of sexual positions and amusing antics. I discovered my favorite was the “spoons position” in which we were lying side by side. I was thrusting my well-used dick up Colleen’s pussy with gusto while fondling her sexy tits as I embraced her. All the while Colleen was caressing my testicles. Of course, I was more than a little bit tired after two substantial orgasms within half an hour. Thus, that erotic act which would have made me come inside a minute when we first got into bed, did not produce the expected third blast of semen. I could tell that non-result disappointed Colleen, too.

She came up with another plan. “Sammy, maybe you could come in my mouth if I gave you a blowjob? I haven’t done that on a boy in about six years.”

I did the arithmetic which indicated that she had last performed fellatio at a rather young age, but I quickly agreed to her suggestion. “Give it a whirl, Colleen!” I said. “Or at least a good licking.”

We both rose from the bed. I stood beside it and Colleen knelt before me. My dick was still hard as a diamond, but whether it could produce another cum shot was now in doubt. Colleen was quite good at what she was doing despite six years of inactivity. I became assertive, putting both hands on her head and thrusting my dick as far into her mouth as it could go. Colleen gagged a couple of times but proceeded like a trouper. It took a while, but I eventually felt an impending cum shot on its way. It wasn’t much, maybe one-tenth of the amount I shot into Colleen’s pussy at the beginning of our tryst, but it was enough to at least coat her tongue so she could show me what I had done. Then she gulped it down without hesitation.

We still had 90 minutes left in our room rental so we both returned to the bed for mostly romantic cuddling. We did include a few lusty gropes every few minutes to remind us that sexual contact was fun. A shower for two concluded our eventful get-together at the Open Road Motel.

As we were leaving, Colleen made a naughty suggestion. “Do you think Fatima would mind if I shared you with her when you two come here on Sunday?”

Before I had the chance to give her an answer, Colleen added, “I guess my first question should have been ‘Do you think you can satisfy the two of us simultaneously?’”

“I could always give it the old college try,” I happily replied.

Colleen promptly corrected me. “In this case it would be ‘the old high school try,’ Sammy. Fatima and I haven’t graduated yet.”