Peggy's Family Tradition

Beautiful teen Peggy Cole is a curious about sex. Her boyfriend is eager, but Peggy's family has an odd tradition about who should be a girl's first bedmate.

Part One

Over my many years as a private tutor, I’ve often reconnected with former students in odd and unexpected ways.

About a decade ago, I discovered one of my former pupils was now a police officer when he arrived on the scene after I was involved in a minor fender bender. (I hadn’t seen him since he was 13 years old. He knew me instantly, but there was no way I would have recognized him as he was now 28 and had a mustache and a beard.)

Another time, when I was buying foreign currency for an upcoming overseas trip, the young lady behind the counter interrupted the transaction to scold me. With more than a hint of fake outrage, she said, “Because you don’t recognize me, I should deny you your frequent-customer discount.” I took a good look at her face, but nothing clicked in my memory. Then she quietly said to me, “My boobs are probably more familiar to you than my face. You used to stare at them all the time!” Within five seconds I knew exactly who she was. “Bonnie Foreman!” I shouted, which caused her to laugh. I only tutored her for a few months a dozen years ago, but I clearly recalled she had a rather voluptuous upper torso for a girl of her youthful age.

Sometimes reconnecting with an ex-student can result in several things coming together that work out very nicely. Take the case of Peggy Cole as an example.

One day I got a telephone reply to my online tutoring ad. The caller said she needed a tutor for her daughter who was struggling with her math course. She added, “I believe you used to tutor one of my other kids.” She mentioned the name Cassandra Cole, but I drew a blank. Then she described where she lived, and everything promptly came back to me. Cassandra was a little girl, about six years old, whom I had tutored in reading basics for about six months. She was one of those students whom I saw for a while, then summer arrived, and the tutoring was temporarily stopped—but it never did resume. It happens all the time.

Anyway, Peggy was two or three years older than Cassandra. I gather I must have said hello to her one or two times when I tutored her younger sister, but I honestly had no memory of interacting with Peggy at all. Nevertheless, after we had booked dates and times for Peggy to be tutored at a nearby library, her mother told me that Peggy was looking forward to seeing me again. “Okay, whatever,” I thought to myself.

Two days later, when Peggy’s mother arrived with her at the library, I almost gasped. There stood one of the most beautiful females I had ever seen in my life. She had an angelic face, a beautiful smile, glistening black hair…and a fabulously sexy body that most women could only envy. She had just turned 18. Wow! Wow! Wow!

I managed to compose myself when I greeted the two of them. Peggy looked at me as if I were an old friend. Her mom said Peggy needed “all the help she could get” in trying to raise her math mark from an abysmal level to a passing grade. She wished me luck and went out the door, saying she’d return in an hour.

I had set up my tutoring paraphernalia at a nearby table that was moderately secluded in an out-of-the way corner of the library. I asked Peggy if she preferred sitting across the table from me or beside me. “Oh, beside you, of course,” she replied, and quickly occupied the chair to my right. She moved it far closer to me than necessary. I did not object.

I quickly found out that Peggy’s mother had a fairly accurate picture of her lovely, young daughter’s math skills: They were pretty much non-existent. Peggy could not do any arithmetic basics in her head. When I asked her what seven times seven was, she shrugged her shoulders and ridiculously guessed 26. She just laughed when I gently told her she was way off. We spent the hour going over all sorts of things that my classmates and I would have known in the third grade forty years earlier.

Peggy was enrolled in a special course at her high school called “Math for Life”—which was mostly basic arithmetic that one needed to be able to function well in society. Her homework was a sheet on converting mixed numbers to improper fractions, but we spent the majority of the hour trying to establish some grasp of math basics. I created a blank times table for her to complete. We ended up doing it together. She had never seen such a thing before and was fascinated by how it worked! “Can I keep this and take it to school?” she asked. When I said yes, she thanked me and affectionately squeezed my hand.

At one point I tried to show her a handy shortcut to doing the nine times table on her fingers. I had her lay her hands palm down on the table. I was going to touch her fingers when the alarm in my brain reminded me, “Teenage girl alert! Don’t touch any part of her without clear permission—even if she’s touched you.” Accordingly, I asked her if I could touch her fingers to show her a math trick. She flashed her million-dollar smile and said, “Yes…anytime you like,” in a very sexy manner. “Hmm, what do I have here?” I thought to myself.

Doing basic math—and having the student finally “get it”—can be very rewarding, so my 60 minutes with Peggy was an hour well spent. We chatted for the last five minutes before her mom arrived. “Do you remember Martin Fletcher?” Peggy asked me, seemingly out of the blue.

“Yes,” I replied after a few seconds of thought. “I tutored him in reading. The last time was about ten years ago, I think. Why do you ask?”

“He’s my boyfriend,” she said. “He says hello and so do his mom and dad.” I had tutored his father, too. He got married early in life because he had impregnated a teenage girl. That teenage girl was Martin’s mother.

“Wow! Small world,” I said. “I remember Martin used to be obsessed with WWE wrestling, toy cars, and monster trucks.” I didn’t say it out loud but I couldn’t help but conclude that Martin had upgraded his interests if he was now spending quality time with the stunning Peggy. “Tell him I say hello—and that he’s a very lucky fellow to have you as a girlfriend.” Peggy smiled at the compliment and ran her hand up my arm in what I considered an overtly sensuous display.

About a minute later, Peggy’s mom arrived. She happily paid me for the session and the two of them left the library. Peggy gave me a cute, girlish wave as she headed out the door. All of a sudden, I envied Martin Fletcher, the little kid who used to endlessly ramble on about monster trucks and the WWE.

I had a lot of things to process from that memorable hour. The four most prominent points were (1) Peggy is very weak at math and will need plenty of work on the basics; (2) Peggy is a smoking hot teenage girl; (3) Peggy chose to sit as close to me as possible; and (4) Peggy was not at all shy about touching me and had no qualms about me touching her.

Later that same night, I got a phone call from Peggy’s mom to clarify the time of a future tutoring session. She told me with a chuckle, “You must have made a great impression on Peggy. She told me you were ‘huggable.’”

I was speechless for a few seconds, but I replied diplomatically by saying, “Huggable? Wow, that’s a new one for me as a tutor. That was very kind of Peggy. I’ve certainly been called worse.” When I hung up the phone, my mind quickly reverted back to Points 2, 3 and 4.

When Peggy and I had our second tutoring session, it was at the same table in the public library we used previously. I was grateful (and frankly thrilled) that we were generally out of eyeshot of most of the other patrons. Peggy became even more liberal with her frequent touching and petting of my hands and arms. I took that as tacit permission for me to be similarly forward with her. I would put my hand on hers when she was trying to figure out a math problem. When Peggy got something right, I would affectionately squeeze it. Each time this small physical action brought a smile to my tutee’s pretty face
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At the end of the night, before her mother arrived at the library to pick her up, I decided to be forthright with Peggy. I bluntly confessed, “I might get into trouble for saying this, but I think you are one of the most beautiful girls I have ever seen in my life. You are certainly the most beautiful client I’ve ever had—and that’s saying something because I’ve had some real lookers over the years.”

“Oh, that’s so sweet of you to say!” she replied. Her face was aglow, radiant with another dazzling smile. This time it was she who squeezed my hand affectionately.

Peggy then saw her mother enter the building. The last thing she said to me before mom got within earshot was, “We might have to do something about this.” Then Peggy squeezed my hand once more. I could feel my pulse rate rising.

When we met again at the library for the third time, Peggy began by saying she needed to talk to me at the end of the session about something urgent. She said we better allot the last 15 minutes of the session for it. Accordingly, after 45 minutes of basic arithmetic instruction, I drew Peggy’s attention to the clock. “You wanted to talk to me about something. So…let’s talk,” I said. Then I added, “I gather this will have nothing to do with the math curriculum.”

I was right. Peggy informed me that her boyfriend, Martin, was pressuring her about having sex. (What a shock!) She candidly informed me she was still a virgin, but she understood that teenage boys liked to have sex with their girlfriends.

“Well, the decision about that is ultimately up to you, Peggy,” I counseled her. “You have the power to say yes or no to Martin.”

Peggy replied, “I understand that, but there’s another part to this that is unusual. In my family, there’s an old tradition: Women should have their first sexual experience with a gentle, seasoned lover. In other words, it should be an older man who knows how to make love to a girl instead of just having sex.”

I immediately sensed where this was headed. I felt a stirring beneath my beltline.
“When my mother hired you to be my tutor, I really liked the idea. You were always so nice to me when you used to tutor Cassandra. You’ve only been my tutor for three hours and I think you are wonderful.” She then kissed me on the cheek, which brought a smile to my face. I didn’t have the heart to tell Peggy I didn’t remember anything about her from my days of reading with her little sister.

Peggy stopped to take a big breath and then sweetly asked me, “Would you have sex with me as my older, first-time lover? Then I’ll be able to make a decision about Martin and me having sex.”

I was about to answer her in the affirmative, but Peggy stopped me from speaking. She held up her hand to add something important. “There’s one more thing: The family tradition also dictates I have to tell my mother about it. She basically has to approve of you taking my virginity. She can say yes or no.”

It might seem odd, but I actually was relieved by Peggy’s mom having the final decision in this matter. I didn’t want to run afoul of the Cole family by running off with their nubile young daughter for a roll in the hay, despite how fantastic it might be. After a long pause, I said, “Peggy, that’s fine with me. Let’s do it this way: Tell your mother we’ve had this conversation. Ask her if I’m acceptable to be your first-time lover. I’ll accept her decision, regardless of what it is. Okay?” Peggy gave me another kiss on the cheek, this one witnessed by a little girl who was passing by our table. She giggled. “I’ll take that sweet kiss as a yes,” I said.

I hadn’t been home 15 minutes before the phone rang. Somehow, I expected the caller to be Mrs. Cole. I was correct. “I’ll get straight to the point,” she said without any emotion. “Peggy told me about the conversation you two had at the end of today’s session. To put your mind at ease, I have no objections at all. In fact, I’ll treat you two to a hotel room at the Convention Center. Because of where I work, I can get a huge discount there. Does this Saturday night sound okay to you?”

I said “yes” multiple times and “thank you” more often than that. When I hung up the phone I intended to break into a celebratory dance, but I could already feel my heartrate rising steadily. Accordingly, I just sat down and relaxed. It was difficult to do, all things considered.

Part Two

I did not see Peggy again until that Saturday night which was three days away. I did get a follow-up call on Friday from her mother, however. She informed me, “I’ve booked the hotel room under my name. I’ll arrive with Peggy. The optics are better; you’re not showing up at a hotel with a teenage girl.” (Amazingly, I had not considered how that might look, so I was grateful for Mrs. Cole’s forethought.) She continued, “You can show up at 7 p.m. Take a cab or a bus so your car isn’t in the parking lot. I’ll have left by then. Peggy will be in Room #709. I can tell you right now, she’s counting the minutes! Have a good time with Peggy, but be gentle with her.” I assured her I would indeed be gentle with her daughter—and I would certainly have a good time.

I knocked on the door of Room #709 at precisely 7 p.m. that Saturday evening. To my utter delight, I found Peggy clad in a sheer, red peignoir. The first sound that came out of my mouth was a deep, lustful guttural chuckle.

“Sorry, Peggy. I couldn’t help myself,” I said. “You look absolutely fantastic,” I sincerely told her. She truly did. It revealed almost everything, leaving very little to the imagination.

“I borrowed it from my aunt,” she said.

“Your uncle is a lucky man!” I retorted, eliciting a gentle laugh from my soon-to-be bedmate.

Peggy sat on the corner of the king-size bed and said, “Let’s be serious for just a moment. I have never done anything like this in my life. I’ve kissed a few boys, but my sexual experience is zero. Does that surprise you?”

“Well, it’s hard to say,” I answered. “It’s not 1950 anymore. Chastity is a rarity today, even for young teenagers. So, I guess I’m surprised—but I’m pleasantly surprised.”

Peggy looked at me with a vulnerable, questioning expression on her face before saying, “Tell me what I’m supposed to do. I’m completely new to this.”

I sat down beside Peggy on the bed and put my arms around her. “You don’t really have to do anything, sweetheart. I’m here to make love to you. I’m going to caress and fondle every inch of your beautiful body, but I’ll treat you like a princess. If you want me to do something specific—or if you want to do something specific yourself—just say the word. Okay?”

“Thanks,” Peggy said softly. “This is a milestone night for me.”

“Hey, it is for me, too,” I insisted. “How often does someone like me get to have sex with the most beautiful girl I’ve ever seen? The fun starts now!”

Fully realizing I was dealing with a sexual novice, I slowly took off my shirt, trousers and socks, keeping my briefs on. I didn’t want to seem too aggressive. I think my passiveness surprised Peggy, but she didn’t say a word to me. I once again sat down on the bed beside this gorgeous female and embraced her tenderly. I slowly removed the peignoir which revealed Peggy’s wonderfully developed bosoms. The only thing she was wearing were pristine white panties. I gently pulled those off. “God, you are beautiful,” I told her. She cutely kissed me on the cheek for that remark. I stood up and removed my briefs. My penis was standing tall. My erection was actually a bit of an obstacle for a moment, as it made it a little bit awkward for me to lift Peggy to the center of the bed. I set her down gently and embraced her passionately.

We kissed for a few minutes and then I explored my bedmate’s sexy body. I gave special attention to Peggy’s lovely tits. After just a few massages, her nipples became hard very quickly. Of course, I sucked on them—as lovingly as possible. I then attended to Peggy’s vaginal area. “You’ll like this I whispered to her.” I proceeded to caress, lick, suck and overwhelm her most private area with sensual pleasures. I could feel Peggy panting and her body convulsing to this unfamiliar feeling. I stopped what I was doing for a moment. “Don’t try to suppress anything,” I advised her. “Just let your body react to what’s happening down here.” Not long afterward, Peggy had a fairly large orgasm.

“Jeez, Peggy, you’re almost a squirter.” I told her between licks of her love juice.

“You’ll have to explain that to me later in more detail,” she said. I promised I would.

Reeling from her first climax, Peggy said sweetly to me, “What can I do for you?”

I said, “Since you asked, you can start by fondling my dick. There isn’t a normal man alive who doesn’t enjoy a female’s hand on his penis.” We both moved to the top of the bed and assumed sitting positions beside each other. I spread my legs sufficiently wide to allow my teen lover perfect access to my dick.

“I really don’t know what to do,” Peggy said apologetically. “Remember, this is all new to me.”

I gave her an understanding smile. “Okay, I’ll help you.” I lifted Peggy’s left hand and put it on top of my erect phallus. “Grab the shaft gently,” I instructed her. She did. “Just move your hand up and down on it.” After a few minutes, I suggested that she massage my testicles with her other hand. Peggy giggled at the idea for a moment, but then she did it with alacrity. I said, “This is what is called a hand job,” my dear, “and it truly feels wonderful.”

“How do I know when to stop?” she asked.

“In my younger days, I’d have you doing this until I blew my load—excuse my crudeness--I mean have an orgasm. But as men get older, their ability to have multiple orgasms wanes. Therefore, if you were anyone else, I’d tell you to stop the hand job so I can cum inside your pussy. But you are so beautiful, Peggy, I think I’m going to be 18 again tonight, just like you. Go ahead, Peggy. Keep doing what you are doing and bring me to an orgasm.”

Peggy laughed at me, but she stayed diligently with the hand job. She commented, “You still sound like a teacher—even during sex.” She was probably right about that. I just shrugged my shoulders.

Not long afterward, I could feel the unmistakable sensation of an impending cum blast. “Oh, Lord, I’m going to cum, Peggy. Let me come on your tits.”

I managed to control myself long enough to straddle Peggy. I could tell she had no idea what to expect. I placed my penis near Peggy’s navel and aimed upward. Nature inevitably called and my dick let loose with several volleys of love juice. My aim was pretty good. Most of the cum ended up on or near Peggy’s lovely breasts. The second shot was stronger than the first; it hit my bedmate under her chin. A weak third shot sent a few drops of my semen into her cute navel.

“Wow, Peggy! Just wow!” I uttered.

“Is that what was supposed to happen?” she inquired.

“Yes, that was one of my better cum shots of recent years,” I informed her. “I was hoping to put it deep into your lovely pussy—but the night is young.”

“That’s true. We don’t have to check out of here until noon tomorrow,” Peggy reminded me.

“Peggy, I’ll do my best to keep you satisfied until then,” I promised.

I washed Peggy with a warm cloth to clean my jism from her beautiful body. For the next hour—until I was rejuvenated in the nether regions—we cuddled, kissed, and used our hands to stimulate each other. Peggy’s kissing was a little mundane, so I coached her on how to me more passionate with her busses. “Let’s do it again,” she insisted after each attempt to improve. It was thoroughly enjoyable.

Finally, when my dick was ready for more action, I Introduced Peggy to intercourse. I was very gentle to begin with, but Peggy seemed to like it rougher than I imagined. I showed her several different positions. To my surprise, Peggy, the beautiful virgin, liked being on top with “the cowgirl”. After she’d sexily ridden me for at least ten minutes, I let loose with another orgasm. This one I gave her no warning about. She just felt my penis spasm and my cum enter her tight vagina. “Oh, that felt terrific, Peggy,” I told her. “You did that like a pro.”

We were still awake at 2 a.m. By that time, Peggy had had her second orgasm—and I had number three. Peggy’s willingness to perform fellatio on me was the stimulus I needed for the third ejaculation. I was tempted to fire the load into her mouth, but the gentleman in me said it would be better to just launch my jism straight into the air and let it fall where it may. Most of it ended up on Peggy’s tits, so I happily gave her the warm washcloth treatment again.

While cleaning Peggy’s chest for the second time, I gently asked her, “How’s your first night of sexual activity been so far, my dear?” This time she was the one who gave off a guttural chuckle. We had one more fruitful romp. I definitely increased my personal level of coital aggression as we assumed the familiar missionary position. I rode her a little bit roughly, pausing a couple of time to suck on her lovely, inviting breasts. I came again inside of her, but it wasn’t much of a cum shot. I was too spent. I apologized to my teen lover for any shortcomings (no pun intended) in my performance. Peggy sweetly said she had loved every moment of our intimacy and thought the whole experience had been “a fabulous treat.” Shortly thereafter, we fell asleep in each other’s arms.

I had arranged for an 8 a.m. wakeup call so we could enjoy breakfast in bed together. That was not necessary, we were both awake by six a.m. and sharing a shower. We dried each other’s bodies with thick, fluffy towels, which was a fun and loving conclusion to a wonderful night. We crawled back into bed and just embraced each other. Our conversation focused entirely on the fucking we had done a few hours before—and basically how thrilling and enjoyable it had been for both of us.

Then something suddenly occurred to me. “Peggy, my love, will you tell Martin about what we did here last night?”

“Yeah, I guess so,” she replied with a shrug. “There’s no point in keeping what we did a secret, as I sort of did it for him.”

“Okay, if you must,” I said. “One thing, though: Please tell Martin for me that his sexy girlfriend was a terrific bedmate. She was the fuck of the century.”