25 yr old hottie with the mind of a tween has me teach her about sex.
PHOEBE’S END
Tender, sweet Phoebe, a quarter century old physically but only half that emotionally, was challenging me intellectually. Her emotional age had her stuck in that awkward stage where your hormones take over your body, rendering her focused on sex. She had become obsessed with me as her mentor, an experienced adult who could teach her all about sex. She was smart, almost too smart, and she was cunning. Her thought processes were well formed and made ultimate sense. She made a sound case for why I should have sex with her, constantly, in order to teach her the finer points of fucking, sucking, and relishing all that such carnal delights offered. But it almost felt criminal to breech that societal taboo against an older man engaging in sex with a much younger woman. Of course, she was of legal age chronologically, yet she was disadvantaged emotionally. I struggled every time I interacted with her. Was I taking advantage of a “handicapped” young girl? Was I truly the lecherous old man fucking a gorgeous, delightful twenty-five year old woman? Was I jeopardizing my career, my status in the family and all that I had worked so hard to achieve by consorting with this siren?
The next couple of days passed by uneventfully. I had no interaction with my “student” so, of course, she kept up her barrage of teenage angst text messages. I ignored them so she reverted to sending outrageous pics again. Pics of her private parts, pics of her pleasuring herself, pics that could get me thrown in jail, throw away the key, if found on my phone. Her messages became pleading, desperation oozing through the phone screen. She sent warnings and threats. I ignored them all.
Rather than risk a potential jail term by a continued tryst with Phoebe, I distracted myself by pursuing Lesley, adding to our captain’s log of sexual visits. Lesley and I were in sync. We were the textbook version of “friends with benefits.” Having investigated our sexual beings beginning at a young age, we had a long history together notwithstanding my move across the pond. Throughout the years we had always been like magnets, attached to each other at the pelvis. Looking back, I believe that the longest we went without sex was a period of six months. Even when circumstances kept us physically apart, we would enjoy mutual masturbation via video calls. Ours was a classic example of unrequited lust and love, just like my grandfather and her grandmother.
As my time in London was coming to an end, I felt a strange sense of duty to wrap things up with Phoebe. It wouldn’t seem right to have enjoyed so much of her without at least saying goodbye in person. A text message just wouldn’t be the same. My return flight from Heathrow to New York was the last flight available for the day, departing at 8:05 p.m. on Friday. I had my staff book me a room at the Heathrow Hilton for the day before. This would give me, basically, two days and one night at the hotel. I made arrangements with Lesley to spend the day before my departure with me at the hotel, maybe even staying overnight. She readily agreed and started working on her excuse to her husband for being gone overnight.
Then there was Phoebe to deal with. I had ignored all of her voluminous text messages and deleted all the X-rated pics she sent. I hadn’t had any contact with her for several days. How was I going to break the ice? How was I going to arrange to see her to say goodbye? It would be awkward to say the least. Yet, I felt almost a moral obligation to at least say farewell and wish her the best in life.
At dinner the talk was all about the goings-on at work, school, and homemaking. Everyone was jovial and the spirits flowed. Then my aunt solved my problems. “Sailor, you’re leaving this Friday and today is Tuesday. We’ve planned a mini “going away” fete with some of the Post’s for tomorrow. Just a simple cookout in the garden, nothing overdone. We’re keeping it small. Just Lauren’s family and Lesley’s family. How does that sound?”
“That sounds great, Auntie. It’ll be nice to see them one more time. I’m not certain when I’ll be able to get back this way for a while. My deals with the Belgian firm are wrapping up and who knows what will come down the pike next. And just so you know, I’m checking into the hotel on Thursday. It will make it so much easier for my Friday flight.”
This was perfect. I’d get to see Lesley socially on Wednesday, then spend at least part of Thursday and maybe Thursday night with her at the hotel. Also, since Lauren, Lesley’s sister, was going to be here, it was a lock that Phoebe would be included. I could say my goodbyes to her at the cookout, avoiding getting trapped by her seductive ways.
That night as I got settled into bed, I checked my emails for any news from the office. There were, of course, a few more text messages from Phoebe. Most were written in all caps and disparaged me for ignoring her. I tapped out a short message to her. “Cookout here tomorrow. Hope you can make it.”
Almost instantly came her response. “I HATE YOU YOU’RE NOTHING BUT A BASTARD PRICK GO BACK TO WHEREVER YOU CAME FROM LEAVE ME ALONE YOU SUCK” I turned off my phone.
Both Lesley’s and Lauren’s families lived on the same block as my aunt and uncle, and they both arrived at the same time. I didn’t see Phoebe. “Hey, Lauren. Great to see you again, thanks for coming. Did Phoebe have a date or something tonight?”
“Hi, Sailor. No, Phoebe had some issues this afternoon. She’s been staying with us, you know, while she gets reintroduced back into society. You know how she is. She knew she was invited, and, for some reason, she went into a teenage tizz, ranting and raving, throwing things around her room, crying, dancing. We gave her all of her meds, but her hormones just went berserk. We told her it would be better if she just stayed home rather than spoil our fun time.”
“Oh, that’s too bad. I was looking forward to saying goodbye to her. I hope she recovers."
"She’ll be alright once she gets ahold of herself. She has these fits every now and again. That poor girl. All grown up yet still a child.”
Everyone was having a splendid time in the back yard drinking, telling jokes and family stories, and generally cavorting with one another in fine fashion. Because the group was all in the yard, Lesley and I couldn’t sneak off into our garden shed “love nest.” We kept exchanging glances throughout the evening, wondering if we’d get the chance to enjoy a quickie at some point. Then Lesley caught my eye and nodded her head upwards, as in “meet me upstairs.” She announced that she needed the loo and went inside. A few moments later, so as not to appear too obvious, I disappeared as well.
In the guest bedroom where I was staying, Lesley and I engaged in a speed fuck. When I entered the room, she was there and already had her pants off, bent over waiting for me. It only took me an instant to get my cock out and ready. She reached around and spread her cheeks for me, and I guided my half hard dick to her pleasure hole. Within a half dozen strokes he was right in the game, pumping into her feverishly. I left my calling card and hurried back downstairs, leaving Lesley to dress and follow in a respectable length of time. Being seen coming down the stairs together would have caused a stir.
When I returned to the back yard, I was surprised to see Phoebe had joined the affair. I made a beeline to her to welcome her and give her a hug, but she sat stone-faced in the chair, her arms defensively crossed in front of her chest. She scowled at me as I brightly said “Welcome, Phoebe! Glad you could join us. How about a hug for Uncle Sailor?” She kept her arms crossed in front of her and gave me looks that could slay dragons. I put my hand on her shoulder saying “Maybe next time. Hope you enjoy yourself.” She brushed my hand off her shoulder and twisted away from me in her chair.
Lesley rejoined the party and we stepped aside, out of earshot, to finalize our plans for the hotel. She was having some blowback from her husband about staying overnight but she was all in for a daytime tryst. Unfortunately, she couldn’t do it on Thursday, so we made plans for her to arrive Friday morning.
Phoebe was watching us intently as Lesley and I were off to one side talking quietly, making our plans. I went inside to the kitchen for a fresh beer and Phoebe made her way there. I hadn’t seen her follow me, but when I closed the refrigerator door, there she was, glaring at me.
“I bet that you and Aunt Lesley were talking about me, weren’t you? You were telling her all about how you took advantage of me and all the sexy things we did, weren’t you? You’re trying to get me sent back to that horrid place in Austria, aren’t you? I just know you are, you cruel prick!” Her bottom jaw began to quiver, and her eyes welled up with tears. “I hate you I hate you I hate you! You’re just like the rest of them! You just want to make me suffer forever and ever!” She broke down crying, burying her face in her hands. In an effort to comfort her, I wrapped her in my arms, but she twisted away. She turned her angry face to me, tears streaming down, crying out “I HATE YOU I HATE YOU I HATE YOU!!”
“Quiet down, Phoebe, quiet down. Can I see you tomorrow, all day?”
These were the magic words. It was as if Niagara Falls suddenly stopped and the sun beamed more brightly than any other day. In less than an instant, she was all over me, arms tightly around my neck, body pressed hard against mine, squeezing the breath out of me. “Really? Do you mean it unk? Really really really? All day? Like for real all day? If you’re lying, I’ll tell everybody our little secret. Don’t lie to me Uncle Sailor just don’t.”
“I’ll never lie to you Phoebe, never. When I became an attorney, oh, yeah, you call them barristers over here, don’t you? Anyway, when I took the oath of office it meant that I could never lie to anybody ever again. I’d love to see you tomorrow, Phoebe. I have a room at the airport Hilton, just like before. I can meet you at the ice cream parlor and pick you up in the morning if you want. Would 9 o’clock be OK?” The look on her face was priceless. It was as if I had just crowned her as The Queen.
When we rejoined the party, Phoebe made a beeline for her grandma, Lauren. They conferred and I saw Lauren nod her head in approval and smile sweetly at Phoebe. The rest of the evening was uneventful other than Phoebe following my every twitch with her eyes. She was laser focused on me.
That night in bed, my phone chirped signaling an incoming text. Phoebe, of course. It read “I’m already all creamy and excited like it’s been FOREVER and I get to go to school again tomorrow and like I’ve never been excited about going to school until now you know so I can’t wait can I come over now please say yes.” She had attached a pic showing her finger fucking herself, two fingers in her twat. I turned off my phone.
Breakfast was the usual dreary hubbub of semi-activity as everyone got their heads screwed back on, getting ready to face a new day. I said my goodbyes to everyone as they went their separate ways, then went upstairs to pack my things. I texted Phoebe “All set? I’ll meet you outside the ice cream parlor in a half hour.” As expected, her responsive video was her jumping up and down and dancing, this time only her top exposed and she was fondling her breasts. She blew an air kiss as the screen went blank.
We were no sooner in the hotel room when the telephone rang. Phoebe disappeared into the loo, probably to change into the hotel robe. I answered the call from the front desk who informed me that I had an urgent message to call my office. I rang them up and spoke to the senior partner. Apparently, my Belgium merger deal was having some governmental pushback, and they needed me to fly there to intervene as soon as possible. He transferred me to the office manager who gave me my flight options. I chose Friday morning, departing at 6:50 a.m. I immediately texted Lesley about the collapse of our plans. She responded with a crying emoji.
Just then, Phoebe appeared. She had applied gobs of makeup and had on the hotel robe, hanging open in the front. She sauntered into the room, adopting a sexy come hither demeanor. I almost cracked up. She had attempted to make herself appear “sexy” but had only achieved the look of a common street whore. I told her how lovely, how sexy, how ravishing she looked, barely containing my mirth. She ate it up like a kid scarfing candy.
“I can dress like this for you any time, Uncle Sailor. Just for you. Now are you ready to give me another lesson?”
I was a bit distracted, not only by her hideous looks, but by the possible troubles I faced in Belgium getting our merger approved. I tried to focus on the matter at hand, examining her luscious body and avoiding the clown makeup on her face. It was not difficult because her body was just right. I approached her and started stroking my hands on her torso, her breasts, her hips. I was enthralled with her body and took great delight in touching it, running my hands along her curves, cupping her modest breasts. I bent my head to hers and engaged in a soft kiss, soon escalating into a passionate embrace.
When we broke, I instructed her to remove the robe and get on her hands and knees on the couch. I knew that the bed was not at a convenient height for what I had in mind. My goal was to invade her ass, completing her “education.” As she prepared herself, I reached for my bag and retrieved the KY lube from by shave kit. “Okay, my dearest Phoebe. Class is now in session. Today we’re going to add the third leg to the milking stool so that it stands on its own, ready for anything.”
“You’re gonna milk me? My boobies aren’t big enough and they’re not full of milk. At least I don’t think they are. Do you want to check, unk?”
I chuckled out loud. “No, no, Phoebe. That’s just a figure of speech. Today’s lesson will introduce you to having your third hole filled and properly fucked. Think you’re ready for that?”
“If you think so, Uncle Sailor. You’re the teacher. And what do you mean by my third hole? You mean my belly button?” I was roaring with laughter inside, but I had to remain serious for my student.
“No, Phoebe, not your belly button. In lesson one, you learned about how to use your mouth on my penis during sex, right?” She nodded. “And in lesson number two, you learned how to use your mouth to kiss. Plus, you learned what it’s like when I use my mouth on your second hole, your vagina. And lesson number three taught you more about how your second hole gets and gives pleasure from my parts, remember?” She nodded. “So that’s two holes, right? Your mouth and your pussy. Right?” She nodded again. “Today’s lesson will show you how to use your third hole, your anus.”
“My WHAT??!! That means my pooper hole, right?” She whipped around from doggy position to sitting on the couch.
“That’s right, my little ingenue. It’s also sometimes called your “back door” or “where the sun don’t shine” or a bunch of other street names.”
“You’re gonna poke your fat thing into my butthole? You’re kidding me, right? EEWWW GROSS! Will it hurt? Why are you gonna do that? What’s it feel like? I’ve never done anything but wipe it with tissue. Do you have to, Uncle Sailor? Can’t we just go back to the stuff I like, you know, like when you had your mouth on my soft spot and made me squirt and stuff. Please tell me that you’re just kidding. I don’t think I’m gonna like this lesson. Let’s just go back to lesson one where you put your boy thing in my mouth. I liked that.”
“Phoebe, you asked me to teach you all about sex. For a man and a woman to keep each other happy, you must learn to use all of the tools and tricks available to you. Your asshole is just one of those tools. Consider now, darling. You have three holes: your mouth, your vagina, and your anus. If you don’t use one of them, then you’ve eliminated one-third of your tools to keep your man happy or for you to get pleasure. In fact, many women enjoy, and some actually prefer, getting fucked in their “pooper hole” as you called it. Now, shall I proceed or do you want to flunk the course?”
Phoebe reflected for a few moments. “Well, I guess it makes sense to be able to use all of my tools. I’m scared though and I don’t want it to hurt. Will you stop if it hurts too much?”
“Of course I will. I have some lubrication gel that will help get things slippery down there. That’s what that tube of KY gel is for. Now are you ready to begin?”
Phoebe gulped hard and looked at me with fear and trepidation in her eyes. “I guess so. Are you sure we can’t just skip over this lesson and go back to the one’s I liked?”
“I’m sure. Now, first I need you to take my cock in your mouth to get him all standing up and hard. Can you do that for me?”
“Gladly, unk. I like this part.”
I stepped over to the couch in front of where she was sitting. She reached out and gingerly took hold of my flaccid meat, holding it gently between two fingers. Her head stretched forward and her lips engaged with my glans. As she began to work him, he began to respond. Within a few short moments, he was firm and turgid, and I grabbed her head and took some liberties fucking her sweet mouth. After a couple dozen strokes I withdrew to her moans of displeasure. “Keep going, unk. I was liking that.”
“Time for you to be on your hands and knees now, buttercup.”
I lathered up my dick with the lube and squirted a big glop on her anus. I used one finger to spread it around, then pushed it inside. She yelped. I continued to push my single finger in and out until she got used to it, then added a second finger. She groaned. More lube and more in and out with two fingers. Her groans of discomfort began to mellow into moans of pleasure. I continued finger fucking her ass until I felt enough gape to allow my cock to make his entry.
I placed him on the target and used my hand and fingers to force him against her sphincter. Her anus was clamped shut tightly. “Relax some little girl. Relax and you’ll really like what you feel. Just open up and let my dick in. It’s all going to be okay, I promise.” I used my fingers to push the head of my cock hard against her hole finding much resistance. “It’s okay, Phoebe, it’s okay. Just relax now, it’s almost in.”
A hard push and he popped in as she squealed. “Ouch, ouch, it hurts!” I didn’t move, I just left him static, barely inside. I flexed him a couple of times and she wiggled her butt. “I can feel that, I can feel him twitching or something. Is it over yet?”
I squirted more lube on ground zero and pushed a bit more. Another half inch slid in. She groaned and I continued pushing until I had two inches inside. Then I pulled out some and pushed it back in. She was making a mix of sounds, some of pleasure and some of pain. I continued sawing my cock in and out, doing a very shallow ass fuck. Eventually she calmed down and started making more sounds of pleasure as her asshole began to loosen a little bit.
“That’s it, baby, that’s a good girl. Just loosen your butthole muscles and let my dick slide in and out. You’re doing fine, just let your muscles loose and it will feel awesome.” My talk helped because her hole loosened considerably and my in and out sawing started going deeper. Within a couple of dozen strokes I had at least four inches buried in her ass. “How are you doing, angel? Are you okay?”
“Yeah, I guess so. It just feels kind of weird, you know? I’ve never had anything go in there before and it just feels sort of like unusual.”
Taking that as an affirmative, I pushed harder keeping the in and out going, gaining depth with each stroke. Soon I had at least five inches inside, so I started fucking in earnest. I grabbed her hips and got a rhythm going, pulling him out to the head, and pushing in five inches. She began to make sounds of pleasure, so I stepped it up. I began forcing him in hard and deep, eventually getting all but the last half inch of my cock up her ass. I pulled her hips back as I thrust forward until I had the whole thing inside and my thighs were slapping on her butt cheeks. I rocked him in and out going faster and harder. Phoebe eventually caught on and started rocking back and forth on her own, fucking me with her tight little asshole. It was nirvana to have her so engaged, such a quick study and such a delightful ass fuck.
I was now getting a real ride, slamming into her, her slamming into me and desperately trying to find the bottom of her bottomless ass. I felt the first tingle of an orgasm building so I turned on the afterburners. I went wild, pounding her hole as hard and fast as I could. Her tiny body was being rocked to and fro and she was moaning and gurgling as I kept ramming my fat cock deep into her. She was reeling as her body was buffeted about. The tingle of my orgasm grew into a roar, and I slammed him in balls deep and held him there as I pumped her rectum full of hot creamy sauce. I twitched and jerked as I unloaded into her delightful ass.
I held my dick deep in her ass until he was flaccid. During the cool down period I praised her. “You were wonderful, Phoebe. Simply wonderful. Are you sure you’ve never done that before because you sure took it like a pro.”
“Really, Uncle Sailor, really? You think I’m a pro? It sure was different, I’ll say that. It kinda hurt a little at first but then it got okay and felt better. My butt is a little sore though. Will it be okay when the baby comes out? It won’t hurt the baby, will it? That’s what we just did, right? We just made a baby. I think I can already feel it in there. Will it be a boy or a girl? Huh, Uncle Sailor? Which kind do you want? I hope it’s a little girl. Would you be sad if it’s a little girl? Maybe you could still play catch with her if it’s a girl, don’t you think?”
“I’m glad if you learned to enjoy that Phoebe. And I’m sorry to disappoint you but we did not just make a baby. Now it’s time for you to get dressed, Phoebe. Uncle Sailor has some work to do. I’ll call a cab for you to get you home and I’ll walk with you downstairs and wait until the cab comes. How about that Phoebe?”
“That sounds nice Uncle Sailor. Thank you for teaching me about all that sex stuff. Maybe we can practice it the next time you come to visit.”