Join the best erotica focused adult social network now
Login

Chaperoning Katie

"Young coed practices handjob skills with handsome older man who isn't exactly who she thought he was"

7
3 Comments 3
5.5k Views 5.5k
2.4k words 2.4k words

Katie entered our world a couple years ago when she rented our studio apartment. At the time, she was about to start her sophomore year in college. Bob and I found her to be a bright, cheerful twenty-year-old woman and a diligent, hard-working student, but unfortunately rather naive and immature. We often tried to serve as mentors for her, and over time, she would begin to confide in us, seeking advice on troubling events in her life. Eventually, we grew to love Katie as though she were our daughter.

However, Katie kept some secrets. Unbeknown to us, she often spent the late evening hours, when she was too tired to study, reading erotic stories, and viewing erotic pictures and videos online. She developed a particular fascination for some alternative forms of sexual behavior, such as giving another person sexual pleasure with one’s mouth or hands. She posted her desires on relevant social media sites and began receiving inquiries from men, most of whom either lived far away in different parts of the country or appeared to be creepy undesirables. She persisted, however, and eventually received an email from a man who lived within easy commuting distance of our home.

As Katie described him, Tom was a fifty-nine-year-old divorced man with two college-age children. He owned a small insurance office in a village about twenty miles away. Though he dated numerous women during the past seven years since his divorce, none of those relationships was successful. He was horny and decided that perhaps a short-term liaison with a sexy, young college woman might just work until he could find another partner. Tom and Katie exchanged a few recent photos of themselves, and discussed possibilities for where and when they could carry out their mutual fantasy, but hadn’t made definite plans. At this point, Katie decided to seek advice from me. I was quite surprised to learn about her possible plans to have sex with a stranger. I never imagined she would be capable of doing something like that.

“And where would you two be doing this?” I asked.

“Could we do it upstairs in my room?”

“Absolutely not, under no circumstances,” I replied.

She looked crestfallen. “Well then, where, in a motel room?”

“That could be expensive,” I noted.

“Melissa, I’m sure I could convince him to pay for it.”

“Listen, don’t make any decisions for now. Think about it tonight and we’ll talk again tomorrow. I think you’re asking for trouble. He could be a psychopath or rapist. I don’t want to have the police knock on my front door one day to inform me that they found your mutilated body in the bushes in a park somewhere.”

Following our conversation, Katie went out for a ride on her bike. When I mentioned a park, she was reminded that the university maintains a large arboretum, with many hiking paths. She rode around the arboretum for some time and finally identified a spot on an isolated knoll, far from any trails or roads. There were several trees and bushes near the top of the knoll, and they could do it there. “It would be so lovely on a nice, warm, summer afternoon,” she thought. When she returned home, she informed me of her plan. It seemed that Katie had no idea whatsoever how dangerous it would be for her to meet a total stranger in an isolated place for sex.

“I’m sorry, but I think you’re taking enormous risks,” I warned.

“Why do you keep saying it’s so risky? It’s just a mischievous, little thing. It’s not as serious as having intercourse, and there’s very little risk of getting any dangerous diseases.”

“Katie, what you’re planning to do is sex, pure and simple. Any form of sex comes with a certain degree of risk because it elicits powerful emotions. Either you or Tom or maybe both could get their feelings hurt. Do you at least have a friend who could accompany you on your adventure?”

“They’re all out of town until classes begin in September. And besides, I don’t want anyone else to see me doing this. You know how fast rumors spread.”

I shook my head. “Well, if you’re set on doing this, best of luck. You have my cellphone number if you need it. Let me know when you’re going to meet him, and I’ll try to be ready to rescue you if need be. I might even be able to convince Bob to come along.”

Katie made plans with Tom for next Sunday afternoon. On Friday evening she stopped by to tell me she thought about what I said, and was beginning to have reservations. She decided to have someone accompany her.

“So you’re still going ahead with it?”

She nodded.

“Would you like me to accompany you?”

“That would be awesome, Melissa. Thank you so much!”

I shook my head in doubt. “Where will he meet you when he arrives in town?”

“I haven’t figured that out yet.”

“How about meeting at the Country Dairy Parlor? It’s right by the arboretum, and we could walk in from there.”

“That sounds good. He wants to see my driver’s license to see if I’m of age,” Katie noted.

“Good idea! You should ask him to show you his license as well to verify he’s for real. And better yet, if you could write down his name and license number.”

Before departing on Sunday afternoon I informed Bob of where we would be going and asked him to call my cellphone every half hour to check if everything was alright. I set my phone to vibrate. Katie met me downstairs. She was dressed in cutoff shorts, a low-cut blouse and sandals, and apparently wasn’t wearing a bra. I thought her attire was too revealing, but I didn’t want to appear fussy over every minor detail.

When we arrived at the ice cream parlor, Tom was waiting for us. He was as Katie described: a clean-cut, handsome, muscular, middle-aged man with a nice tan and a touch of gray hair in his sideburns. He looked at least ten years younger than his age. He was wearing a colorful polo shirt, shorts and sandals. Katie had already informed him that I would be accompanying her. He wasn’t pleased about that but acquiesced. After the introductions, he offered to buy us both ice cream. Katie accepted. They exchanged licenses to verify ages, and everything checked out. Katie led us to the site. It was as she said – very secluded. Tom immediately began disrobing and was soon standing stark naked before us, looking hunk-like.

“Aren’t you getting undressed?” he asked Katie.

“I think I’ll pass,” she answered.

“That’s too bad. I was hoping you’d show me your lovely tits.”

“Tom, I’m sure you’ll get sufficiently aroused anyway. See, you’re already getting a serious hard-on. Why don’t you lie down and make yourself comfortable?”

Tom complied, lying flat on his back, legs outstretched, his hands clasped behind his head. He seemed at ease and completely unabashed about his nudity. Katie dropped to her knees, placing one leg on each side of Tom’s legs, and lowered herself until she squatted on his legs.

DalilaMile
Online Now!
Lush Cams
DalilaMile

“And what about you?” Tom added, turning to me.

“I’m not part of this, and won’t be involved in anything sexual. I’m just here to see that everything goes okay.”

Katie seemed self-confident and knowledgeable and probably had rehearsed details beforehand in her imagination. She set a small bottle of hand lotion aside, then leaned forward, placing one hand on each of his shoulders, and began massaging his muscles. By then, Tom had a very firm erection, which was now pointing sharply upward. I was fascinated by what was taking place. She methodically moved down his body, brushing the hairs of his chest with her hands in light, swirling motions, then gradually moved to do the same on his abdomen, sometimes also teasing him by dragging the tips of her nails over his skin. By the time she reached his groin, his taut manhood was twitching. Katie combed his bush with her fingers, then slid her hand down an inch or so, placing her thumbs at the base of his erection, and began massaging his balls. I actually found the action to be quite erotic, and felt myself starting to get wet.

Bob buzzed me. It was an inconvenient time. I wanted to watch the action. I quickly texted him to say that all was fine.

It was clear that Katie had him under her control. After she worked his balls for a minute or so, she took the bottle of lotion, poured a generous amount onto the palms of her hands, and then slid her hands slowly up and down his shaft. She then formed a ring with her thumb and forefinger and moved her hand back and forth across its swollen head in short strokes to stimulate the sensitive areas in the corona. Tom moaned softly and fidgeted. He was ecstatic. She returned to stroking his shaft with firm strokes, occasionally twisting her hand around it. Soon, a small, clear drop of thick fluid oozed from its opening.

“How are we doing?” she asked.

“Unbelievable,” he moaned. “I never imagined it would be this good.”

Katie glanced furtively in my direction, grinning.

“Where did you learn all this?” he inquired.

“From reading stories and watching videos online,” she replied.

“No way. Not from practical experience?”

“Nope.”

“Well, you’re already a pro,” he added.

With that, she increased the pace of her stroking. Tom became more tense, and thrust his hips upward, forcing his erection firmly into her clutched fingers. He opened his eyes for the first time and began staring at her eyes. She diverted her gaze back and forth between his eyes and his cock to gauge his reaction. It wasn’t but a few seconds later that Tom’s breathing became louder and more erratic, and he winced. Without further warning, he began shooting his load, groaning. Ribbons of cum shot from his throbbing organ, spraying rapidly in all directions, showering his chest, abdomen and pubic area.

After the spurting diminished, the two sat in silence for a few moments while Tom tried to catch his breath. He placed one hand on each of her arms and stroked them softly, his eyes still fixated on her face. Katie sat back and released her grip on his now deflating manhood, as a radiant smile beamed across her face.

It seemed sad that the action was over in less than five minutes. I was totally fascinated by everything I observed, and had to confess that for all the sexual encounters I’ve had with men, including my husband, I never experienced a man’s orgasm so visually, like this. I never knew exactly what happened during ejaculation.

Unfortunately, the euphoria of these few minutes on this idyllic, summer afternoon would prove to be short-lived.

“You know, Katie, I could get addicted to this very easily,” Tom said. “How do you feel about doing this again sometime? You were incredible. Maybe next Sunday, same time and place? I could give you pleasure too, in return.”

Katie glanced quickly in my direction, seeking advice. I shook my head vigorously, indicating that she shouldn’t meet him again. She sat quietly thinking about what to say to him.

“I only intended to do this once for fun, and not again,” she answered. “Don’t you think it would be better if you found someone more your own age, and teach her how to do this?”

“My own age? Most of them look like they could be my grandmother. They’re all traditional ladies, and wouldn’t be into something like this.”

Katie kept glancing in my direction looking for guidance. I kept shaking my head side to side.

Suddenly, Tom turned toward me and shouted, “You stay out of this, bitch, you hear? This is just between Katie and me. She doesn’t need your advice.”

I was shocked at how the tone of this seemingly mild-mannered man had suddenly become harsh, vulgar and threatening.

“But Tom, we wouldn’t be good for each other,” Katie pleaded. “Do you realize that you’re fifteen years older than my father?”

“I’m not trying to be your dad. I just want some intimacy every now and then. You wrote in your blog that you’re fascinated by men’s sexuality and love to do handjobs, so what’s the problem?”

“Tom, I’m not looking for an ongoing relationship with someone. As I said, if you tried someone closer to your own age, you would be more successful. I can’t be a substitute for a real partner.”

“Well, not even just one more time?” He persisted.

Frustrated, Katie placed her hands over her face and began weeping. “I’m sorry; I can’t, Tom,” she tried to say, forcing her words from her throat. Please don’t nag me.”

“Then get off of me and get the hell out of here!” Tom yelled.

I quickly rose, rushed over to Katie, and helped her get up. “Come on, hun. Let’s go.”

Katie threw her arms around me, rested her head on my shoulder and sobbed.

“Come on, let’s go,” I urged.

Katie and I walked briskly downhill. When we got about halfway down, I grabbed her elbow and told her to follow me. I started running. "Let’s head for the woods over there and hide."

She followed, and we ducked into the woods and found bushes to hide behind. I looked back to see if Tom was following us, but he was probably still getting dressed. We stayed there, kneeling on the ground until I saw him walking downhill toward the ice cream parlor, where his car was parked. We waited a while longer just to be sure. Bob buzzed me again, and I confirmed we were fine. By the time Katie and I returned to the ice cream parlor, Tom’s car was gone.

Back at home, Katie and I hugged again. I lifted her face up, looked into her tearful eyes, and stroked her hair. “Why don’t you go upstairs and get some rest. Later this evening, join us for dinner. Okay?”

She nodded and walked slowly upstairs. Soon, I heard her sobbing uncontrollably again. Poor Katie.

 

 

 

Published 
Written by SammyL
Loved the story?
Show your appreciation by tipping the author!

Get Free access to these great features

  • Create your own custom Profile
  • Share your erotic stories with the community
  • Curate your own reading list and follow authors
  • Enter exclusive competitions
  • Chat with like minded people
  • Tip your favourite authors

Comments