A darling lass, 25 yr old chronologically but a pre-pubescent teen emotionally, has me teach her about sex.
INSIDE PHOEBE
The darling little Phoebe, emotionally challenged, had just gotten her first tongue lashing from yours truly. The smooth, hairless slit, the fragrant aroma of a nubile snatch, the sweet juices she produced had given me as much pleasure as she had absorbed from my lesson. Phoebe was obsessed with anything sexual, having been halted in her emotional development at that critical stage where all your hormones come together and define your sexuality. It was a bit disconcerting to be faced with a 25 year old body inhabited by a tween brain. The disconnect was troubling on so many levels.
The ride home was one-sided. I drove methodically, a stern look on my face, trying to sort through what had just happened. Although I had broken no laws, I had certainly stretched the boundaries of what society considers morally and ethically appropriate. Certain actions are widely considered taboo by so many. The other side of the ride was a joyful, bouncy, teen. Phoebe was in high gear, chatting incessantly, rambling on and on about the orgasm she had just experienced, cooing how she couldn’t wait for our next lesson. Then she’d go quiet and poke at her phone, squealing with delight at some TicTok post or a screen full of emoji’s sent by one of her online friends. Then she’d start bouncing around, dancing in her seat, and singing a made up song about making babies or something with her hand between her legs, rubbing herself raw. She was a woman possessed.
Fearing that we would be seen arriving together, I drove to the ice cream shop a few blocks from home. “Ooohh, ice cream! Is that a treat for being such a good student? Huh, unk? Will you buy me ice cream every time we have class? I can’t wait for our next class. When will that be, huh Uncle Sailor? When, when, when? I’m already creamy just thinking about it." Another swipe between her legs, a few rapid stabs of her fingers in her hole, and the obligatory suck them clean. “Uhmmm … tastes so good! Want some?”
We got our treat and sat at a corner table, removed as far as possible from the few others inside. “Phoebe, you must listen. You have to keep our class lessons absolutely private. You are not to tell anyone, I mean anyone, about this, do you understand?”
“I think so. But why can’t I tell anyone? I mean, I’m glad that you’re teaching me and everything and like it just feels so good and like I want to shout it to the world. Why can’t I tell anyone, unk? Did I do something wrong? I mean like today I got really wet down there like I mean really wet and it went on your face and everything and I should warn my friends and let them know what happens, right? I mean it’s just normal you said, right? Why can't I tell anyone?”
“It’s not quite as simple as you describe, Phoebe. All the adults, the old people like me, would not like to hear about such things. If you told even your best girlfriend and she told her parents. Well, let’s just say that both you and I would get in a lot of trouble. Please trust me on this, Phoebe. Pinky swear that you won’t tell another soul, okay?” I held out my pinky finger and gave her a stern glare. She looked crestfallen, frowned and hooked her pinky to mine. “Pinky swear” she said.
“Thank you, Phoebe. Just understand that if you break your promise, there will be no more classes, no more good feelings down there.”
Dejected, she hung her head low “I understand.”
“Now, Phoebe. I need you to do something for me. Can you do that for dear old Uncle Sailor?”
She instantly perked up, her eyes alight and sparkling again. “Sure, unk, anything, like anything. Tell me what you want me to do and I’ll do it, okay? Do you want me to keep practicing on your thingy like I did before? You know, like kissing it and letting you push it in my mouth? Is that what you want me to do? Because you know I’ll do that anytime you want, just anytime it feels so good and it gets me so wet and creamy down here you know.” She slid her hand up her skirt once again.
“No, Phoebe, not that. What I want you to do will require you to be like a detective, investigating a crime. But you can’t get caught, okay? You must be very careful to not get caught. Can you do that?”
“I think so. You mean be like Sherlock Holmes?”
“Exactly. What I want you to do is to pay close attention when your mom gives you your daily pill. See if you can read the package the pills come in. Remember what the package says, maybe even take a pic with your phone if you can do so secretly. But don’t get caught, don’t be obvious. Be very secret about it, okay, Phoebe?”
“Sure Uncle Sailor. I’ll try.”
“Okay, that’s a good girl, Phoebe. If you can do that without getting caught, then I may have a special surprise for you at our next class session.”
I thought she was going to dance on the table. Her face was radiant as she got super animated and twisted and turned in her chair doing a teenage dance move, her arms punching the air overhead. “A surprise! I love surprise presents! I can’t wait!”
I explained to her that it wouldn’t be a good idea for us to drive home together. I told her to walk home and tell her mom that she went to the movies or just hung out downtown.
I left Phoebe and drove to my aunt’s house. I didn’t see her car in the drive, so I parked and walked over to Lesley’s. She answered the door, somewhat surprised to see me.
“Are you alone, my little sex kitten?”
“Absolutely, but only for the next couple of hours. Please come in and come in.”
We spent the next hour or so actively exploring each other’s intimate body parts. Lesley wanted to bone up on her fellatio skills. “I don’t get to practice this much anymore. Do you mind being my Guinea Pig?” What was a fellow to say. She had no trouble during the initial intake but struggled a little getting me past the back of her throat. Once she conquered that it was smooth sailing. We spent nearly an hour trading off who was doing the fucking. I was unusually randy and was able to coat her mouth and her face three times. The first one was the biggest and best, delivered deep down her throat, her head held securely up against my abdomen. It was the result of a spirited pounding, her head held tight against my body, my cock repeatedly slamming down her throat. My eyes were closed and I was visioning that I was deep in Phoebe’s snatch rather than balls deep down Lesley’s throat.
After dinner we played a few hands of cards and downed a few beers. The table conversation was mostly about the game, not family matters. Light and meaningless. Suited me just fine as I was still beleaguered about my clandestine meetings with Phoebe. My two heads were at war with each other, and I was struggling to rationalize it to myself. My top head knew, was unequivocally convinced, that what I was doing was wrong. And it wasn’t just the age gap issue. It went beyond that, given Phoebe’s emotional condition. Then there’s the lecherous old pervert, using his bottom head. Yeah, she’s 25 years old, nothing wrong with that except the age gap thing. Fuck a bunch of people who don’t know that age is just a number. Yeah, she’s an easy willing mark. Who cares if she gets a little damaged. You’ll be dead and gone and, shit, she’s already damaged. And, oh, yeah. She’s scrumptious. How often will you have this opportunity that has been served on a silver platter.
Tucked tightly in bed, I turned to my phone to check on work. All quiet on the Eastern Front. And I had a half dozen texts from darling little Phoebe. The first couple were just her spouting off about how wonderful I had made her feel earlier, how much she wanted more, and goofy adolescent girly stuff. Then came the message I was looking for, complete with a pic. Yasmin. Her mum fed her the Yasmin brand of birth control. Phoebe’s message with the pic of the box of Yasmin was hilarious. “Is this what you want Uncle Sailor? My mum gives me pills from this package every day. I don’t think it’s what you want to see, though, I mean, like, my name is Phoebe, not Yasmin. I’d have to be named Yasmin for them to work on me, right? Maybe she’s just fooling me, I don’t know. Does this mean that we can’t have any more lessons, like, you know I did what you asked and everything and I really want the surprise you promised and like I’ll just die if we don’t have class again. I’m getting all excited now just thinking about it, having more school with you, it feels so good I’m rubbing myself right now can you tell?” The next one, sent a mere five minutes later “I got myself all creamy just for you, unk. Could you tell, I mean it was pretty good feeling and everything so I’m sure you could tell. And when do I get my surprise and when do we meet for class? Will I get my surprise before or after school? I can’t wait, unk, I’m all wet and rubbing myself waiting to hear from you. WHERE ARE YOU, JERK? ANSWER ME!” I chuckled and rolled over to sleep.
The morning was a repeat of the day prior. Coffee, breakfast, idle chitchat about the drudgery of work and school. When everyone gathered up to leave for their day of toil, I feigned that I had some errands and had to visit a central London barrister office for some unspecified work related thing. Once I was around the corner, I texted Phoebe. “School starts in a half hour. Meet me outside the ice cream parlor in 15 minutes and I’ll give you a ride.”
Once again, Phoebe’s reply was a short video clip of her dancing, excitedly jumping up and down and clapping her hands. Only this time, she was buck naked. I shook my head with a wry smile unfolding on my lips and headed to the local pharmacy. I bought some sex lube, some candy, and a couple of teen magazines for Phoebe. When I pulled up to the ice cream parlor, Phoebe was standing on the sidewalk talking to some strange looking man. He had on a long trench coat and scruffy hair, like he was a bum or a beggar. He had his hand on her shoulder, and the picture just didn’t look right. I stopped, put the car in park, and opened the door. I stepped out and called to Phoebe. She turned to come my way, and the street bum held her jacket shoulder, trying to keep her there. She twisted and broke his grasp and sprinted to the car.
“Oh my God, unk, he was awful he smelled like a rotten dustbin all poopy and pissy. He wanted to know where I lived and if he could come see me and if I came to the ice cream shop often and he had ugly, rotten teeth and stinky breath. I’m so glad you got here I don’t know what I would have done without you but I’m okay now.”
I was disturbed by what I had seen and what Miss Phoebe had said. I used the ride to the Heathrow Hilton to discuss the situation with her. For someone with a stunted grasp on her emotions, she actually understood the dangers quite clearly. She gave me a blow-by-blow narrative of what she would have done had she been alone in that situation and her plan was sound. I felt relieved that somewhere along the line she had been advised about “stranger danger” and what to do.
Once in the room at the hotel, I called the front desk and ordered a beverage cart. When I turned back to the room, Phoebe was again in one of the terrycloth robes provided by the hotel. She was staring at me with the sexiest look known to mankind, her hand at her mouth, one fingernail between her teeth, her head tipped down with her sexy eyes peering up at me, a shock of her pretty brown hair cascading down across her face. “I hope you brought me a surprise Uncle Sailor. Is that what’s in the bag?” As she said this, she nonchalantly brushed one side of the robe open sliding one foot forward, revealing smooth, taught, flawless skin. This vixen was destined to make some lucky man very happy.
Even though I had serious moral qualms about what I was doing, at my age I had given up. I stepped over to her, slipping one hand under her robe and around her skinny waist, the other on the back of her neck and bent down to kiss her. Phoebe obviously hadn’t engaged in any serious kissing before, but she took to it like a bird to flight. She responded with overwhelming passion, quickly learning how the tongue is integral to the process. We kept our lips busy, our tongues busy and our hands roamed over each other’s body. She had just discovered my rock hard cock and was stroking it through my pants when the knock came.
“What may I get you from the bar my turtledove?”
“A rum and coke if you have it. A beer if not.”
Phoebe was reclined on the couch, half sitting, half lying, her back against the arm, her lovely legs stretched out on the cushions. She had arranged the robe so that just the right amount of skin was showing but her love pieces were shielded from view. Tantalizing, erotic, tasteful. Your eyes wanted to fill in the hidden spots, wanted to see more. I settled in near her and set my bag of goodies next to her. Her eyes blazed wide open, regaining that innocent, childish wonder. “Is that my surprise? All for me? Oh, Sailor, you’re wonderful!” She tore into the bag and pulled out the teen magazines, her eyes wide with joy. “Oh, Sailor! How did you know? This is my favoritist of faves all time! I can’t wait to read it!” She gave me a loving look and smile. Same reaction to the next magazine. Then came the candy to Ooohhh’s and Aaahhh’s, interspersed with some high pitched excited teenage girl noises.
When she finally got to the sex lube she furrowed her brow. “What’s this? It says KY jel. Is it some kind of hair gel or something, like I’ve never seen this kind before so is it like something new or does it do something different? What’s this for, Sailor?”
I inhaled most of my scotch. Standing to get a refill I casually said, “You’ll see, pumpkin, you’ll see.” I refilled my drink and resumed my position on the couch. Phoebe suddenly pushed her presents aside and lurched forward, throwing her arms around my neck, the robe flying open to reveal her picture perfect body. She smothered me with kisses, “Oh, you’re really the bestest ever, Sailor. Thank you so much for my presents I love them and I can’t wait to read my new magazines and eat my candy and wow you’re just so wonderful!” I turned and pulled her head to mine, planting my lips solidly on hers. We enjoyed a passionate kiss and my hands got frisky with her diminutive breasts. When I tweaked her nipple, she squeaked out a girly squeak and doubled up on her kissing passion, pressing against me like I had just saved her life.
When we broke, I stared at her pretty face and stroked her hair and cheeks, counting my blessings that I had such a godsend sprawled across my lap. I moved my hand down and began toying with her magical triangle. Slowly, seductively she murmured “Is class starting now?” My fingers traced her slit, then parted her lips. She needed no KY lube; she was primed. I worked on her clit, rubbing circles around it as she began moaning and twitching her hips. I got more forceful, pushing, smashing, twiddling it, making it assume an upright, firm posture. I squeezed her clit and massaged it, eliciting more feverish moans and groans, increasing in frequency as she arched her back until she cried out “Oh fuck oh fuck oh fuuucccckkkk!!” Her cunt flooded and she let her body relax. Her pretty eyes sought out mine, hers fluttering. “We just made babies, didn’t we?”
I nearly lost it. It took every bit of self-control I could muster to stifle my laugh. I merely smiled and said, “Not yet. Not quite yet, darling.”
Phoebe rose and disappeared into the loo. I took the opportunity to call room service and order us some lunch. By the time she returned I was ensconced on the couch again, nursing my drink. She sat next to me, her robe wrapped around her. She leaned into me and rested her head on my shoulder as I worked my drink, hoping that I could find some answers at the bottom of the glass.
She put her hand on my thigh and began petting, gently rubbing it around. Eventually she got it close to my equipment, brushing against it. “Is class still in session, unk? Do I have any homework? When’s the test coming? I think I need to study if I’m going to learn how all this works.” She reached her other hand over and found my cock, soft as a croissant. “Uh oh. He went away again unk. Like, do I get extra credit or something if I can make him return? Huh, unk, how does your grading system work? What do I have to do to get an A? You know I always get the highest grades in the class like everyone comes to me for help and stuff. What’s my grade in this class unk Sailor? Huh, huh?” The whole time she was talking, she kept stroking and rubbing my dick, getting him to firm up nicely.
Fortunately, there was the expected knock at the door, saving me from destiny. Phoebe was astounded at room service in a classy hotel. The beverage cart held nothing to the opulent spread that two hamburger plates entailed. She chatted on incessantly in her teenage-speak, wolfing down the French fries and nibbling at the sandwich. As she ate, moving her arms around, her oversized robe had parted in the front, falling open just enough for me to enjoy a view of her small but firm breasts. With such a view, the hamburger became tasteless, nothing more than fuel.
Once lunch was complete, Phoebe started up the sex talk again. I knew it was now or never. “Okay, Phoebe. You’ve graduated from level one to level two. Now it’s time to move the lesson into the bedroom.” She did her little jumping dance, clapping hands thing, the robe opening wide in the front. I grabbed the lube and went to the bedroom, shedding my clothes. By now, the anticipation, staring at her tits and the robe exposing her body had gotten a rise out of my cock. He was standing at half-mast and Phoebe, not knowing quite how to proceed, was standing next to the bed with the robe still hanging open at the front.
“Look unk, look” pointing at my sprouting dick. “He’s starting to recover.”
“Yes, darling, that’s right. And shortly he’ll be standing at attention before he disappears inside you.” She clapped and jumped like a cheerleader again. I guess that’s what teenage girls do.
I stepped over to her and pushed the robe off her shoulders, wrapping my arms around her and pulling her close into a sensuous kiss. We embraced for a minute as my cock swelled to full size. Then came the moment of truth. “Okay, Phoebe. We spoke about the different positions that people usually have sex in. The one you described is called “Missionary” position, the man lying on top of the woman. Another popular position is called “Doggy Style.” At this reference she hooped and hollered.
“Doggy Style! Are you kidding? Why would they call it that? We’re both humans, people. Why don’t they call it People Style?”
“Well, have you ever seen two dogs having sex?”
“No, I don’t think so. I can’t remember.”
“Okay, Phoebe. Get down on your hands and knees, pretending like you’re a dog.” She did. I stepped around behind her, crouched down, and aimed my dick at her hole. When it touched her slit, she jerked. “No, no, Phoebe. Stay still. You want to learn about this sex thing, right?” She nodded with an umhuh. I rubbed the head of my dick up and down her slit, getting the lips to part. She started to make guttural moans. Once I had enough of her natural pussy juice to lube things up a bit, I pushed, just enough for the glans to enter her.
“Oh, I don’t know, Sailor, I’m scared, it’s gonna hurt isn’t it I can feel it already I’m not sure I can do this.”
“Okay, Phoebe. Let’s try another position.” I climbed on the bed, lying on my back. I got some KY and lubed up my shaft. “Up here, Phoebe. Come straddle me.” She climbed on, sitting on my stomach.
“I’m scared Uncle Sailor. Am I doing this right? I’m afraid I’m gonna break something or it’s gonna hurt or I don’t know.” Her pretty eyes welled up with tears, and you could tell that she was tense and afraid.
“It’s all going to be okay, Phoebe. Just relax. I won’t hurt you. Just think how many people have done this before. You’ll be fine. Okay now, raise up your butt and slide back a little, that’s it, you’re doing fine.” I took hold of my cock and found her pleasure point. I rubbed it back and forth to part her lips, the KY helping. “Now, Phoebe, just start slowly lowering your butt down, like you’re going to sit on my lap.” As she did so, I kept my hand on my cock to give her a limit and she gently settled downward, allowing my dick to spread her vagina open. Her face was a study in fear, terror, and uncertainty until she had an inch or so inside her. “See, baby, see? It’s not so bad. That doesn’t hurt, does it?”
“It doesn’t really hurt so much as it just feels weird. It doesn’t feel like the hairbrush handle I usually use.”
I removed my hand from my cock and cupped her perfectly rounded ass cheeks in my palms. I gently lifted her and let her slide down, up and down, up and down. With each down motion an additional inch or so of my cock disappeared up her twat. And it was tight, oh so tight. I was afraid that my girth would be too much for her narrow tunnel, but it seemed to slide in without too much resistance, and she wasn’t crying out in pain.
After a few dozen strokes, she got the hang of it and started lifting and lowering herself. The expression on her face had changed to one of satisfaction. “Oh, Uncle Sailor this is feeling better now I was so afraid and you helped me and ohhh ohhh it’s going in farther now ohhh ohhh how far can it go how much more is there oooohhhh that’s feeling good I think I like this ooohhh yes I definitely like this.”
With her accepting over half my dick I pulled her down against my chest. “Are you ready for some real sex now, Phoebe?”
She raised back up, a horrified look on her face. “I thought this was real sex, have you been fooling me, taking advantage or something? What’s going on, what do you mean real sex?”
I pulled her back against my chest. Cupping her tender butt cheeks in my hands I started thrusting upwards, getting an additional inch in with each stroke. I pushed and pushed and she began breathing faster and moaning. I kept fucking her sweet little cunt going deeper until I had my fat cock all the way up her pussy. All the way. I stopped thrusting with it deep inside her and pushed her shoulders back up so that she was sitting upright. “See, Phoebe? You have my entire dick inside you right now. How does it feel?”
Her gaze was unfocused, as she said “It feels like I want this all the time, unk. I love this feeling.”
I pulled her back down and, with my hands spreading her ass cheeks, I began fucking her hard, non-stop. After all, this was an adult body I was fucking, even though it was occupied by a teen. I began pounding, jackhammering her from below. Phoebe’s body was bouncing around on top of me as I pounded hard and deep, giving no quarter, taking no quarter. Simply doing what most men only dream of. Pounding the hell out of a sweet young twat. Phoebe was being thrashed around on my chest, and she was making all sorts of noises. Grunts, groans, yips, squeals, guttural noises from I don’t know where. I ravished her cunt for as long as I could last. Then I slowed it way down and slid my cock in slowly, tip to balls, in an even pace. Seeing her stunning beauty as my dick slid in and out of her finally caught up with me. As my orgasm boiled just below the surface, I pumped him in deep and held him there as I emptied myself at the bottom of her well. I gave her five giant squirts of jism, five spasms, five hard jabs, one for each shot.