Chapter 11:
Teaching Patty
As the appointed time approached, I drove the dinghy to shore and got to the right place, at the right time. I saw a very attractive young girl sitting alone at the bar. “You Patty?” “That’s me, in the flesh and blood!” She was easily an 8.5 on a 10 scale. Shoulder length auburn hair, just a touch of eye makeup that made her soft brown eyes stand out. Her face was easy on the eyes, and she was dressed just so. Fairly conservative clothes but tight enough and low cut enough to titillate but keep the allure alive. She had a tight waist, flat belly and hips that just begged to be grabbed from behind. Her boobs were just the right size – not too much, not too little. She wasn’t sizzling hot but certainly smokin’ hot. We got to talking, first about business. Just about what I needed done on the boat, her relevant experience, and her rate. She passed that interview.
“So, what do you do when you’re not cleaning boats?” “I’m a part-time receptionist at the local insurance office. Kinda boring but keeps a roof over my head. And what about you?” “Oh, I’m just a horny old, retired guy sailing from port to port, still searching for that elusive mermaid to join me.” “Maybe you won’t be so horny once you find her. Just what are you looking for?” “Well, that could get kinda personal. Don’t want to scare you off so soon. We’re just getting to know each other.” “Oh, no. Please! Share all the details with me. Don’t be shy! I’m very open minded and want to learn as much as I can. I’m not very experienced and need to learn more, especially from a seasoned veteran such as yourself.” “I’d be happy to give you all the graphic details. But not here, too public. Plus, I’ll need some alcohol to loosen my tongue.” “Well, my place is nearby. I don’t usually invite men over that I’ve just met but you seem relatively harmless. Wanna come over?” I jumped at the chance. I paid our tab and we drove the short distance to her apt.
Once inside she poured me a generous glass of bourbon on the rocks and a gin & tonic for herself. We settled down on the couch, her at one end, me at the other and started in on our booze. “So, tell me what you’re looking for in your elusive mermaid? What’s she like that will satisfy your horniness?” “Well, this is kind of awkward, but….” Nervous as a cat I took a big slug of my bourbon. It warmed my throat, and I could feel the tension start to melt away. Did a bottoms up and asked for a refill before I continued. As she sauntered to the kitchen, I watched her backside. Yes, yes, it was a lovely sight. Tight waist, ample hips, proportional thighs. Just right. As she returned, drink in hand, she never took her eyes off me. Her expression was very soft, amiable, and inviting, a slight grin showing. Her soft brown eyes had that unmistakable twinkle about them while also telegraphing a seductive ‘come hither’ message. I took another big swallow and continued. “Well, Patty. I’m really nothing more than a lecherous, dirty old man. When I was married (a widower now, God rest her soul), the last 15 years were without sex. Maybe a perfunctory missionary, wham, bam, thank you ma’am once a year. But a man has needs. So, I just jacked off. A lot. A whole lot. Even at work I’d disappear to the men’s room and whack off. I’d masturbate 8 or 10 or 12 times a day.” “Wow. My condolences on the loss of your wife. But that constant masturbating seems excessive. Why didn’t you date?” “That’s difficult to answer. Inside, I’m really very shy. And I totally dissolve when rejected. I go into a shell. My sexual needs were so great that I couldn’t just ask someone out. All I wanted, all I could think about was having my dick in one of her holes or having my face buried in her pussy. That doesn’t make for a good date, does it?” “No, probably not. But you don’t come across that way to me.” I took another deep drink. I pondered for a moment as I drained my bourbon. “I’ll let you in on a secret if you refill my drink.”
Once again, I got the delight of watching her near perfect backside as she walked away. Very sexy indeed. As she returned her expression had changed to one of surprise coupled with questions. Her soft brown eyes, fixed on me again, were now showing compassion and intrigue. Took a big swig and said “The secret is that from the moment I laid eyes on you, my thoughts have been focused on what you look like naked, what you like to do in bed, how good are you at sucking and fucking, and how far will you go. Just how nasty and dirty you’ll get. In fact, my dick’s half hard right now just being with you and talking like this.” She instantly looked at my crotch and saw the outline of my semi-rigid cock. She let out a short giggle and looked at me, her eyes wide with surprise. She said “Lord almighty! I didn’t even notice. And I had no clue you were having those thoughts. I told you that I’m not very experienced and wanted to learn. So far you’ve given me quite an education.” “Well, Patty. Can you answer the questions that have been rattling around in my head?” “Uh … you kind of put me on the spot. I’m open minded and all but I’m just not sure. Kinda timid. Maybe another drink and some more talk might help.” “Of course. I don’t want to force anything. Go make a stiff drink. Then we can talk some more.”
As she disappeared into the kitchen, I found the bathroom and took a piss. When I returned, our fresh drinks were on the table, but Patty was gone. Shortly, she reappeared from the bedroom. She had changed into much more revealing clothes. A see thru top, no bra, nipples clearly visible and a very short mini-skirt that didn’t really cover much. She sat on the couch, facing me now, with her legs spread enough that her lady parts were quite visible.
“Where were we, my dear?” I asked. “I have some questions if you don’t mind” she said. “Not at all. Shoot.” “So, what’s your favorite position?” she asked. “Easy one. Doggy style. I can just stand there, and I have access to both holes from one end and the third from the other. Next.” “Well, which hole do you like best?” “They’re all equal, Patty. That is if the woman has any talent. Deepthroat and anal are sublime yet I love to alternate between asshole and pussy also. If she’s no good at giving head, then ass fucking is my next best favorite.”
“Well, I had sex a few times in high school, but it was pretty basic teenage stuff. Nothing like what you’ve described. Just basic backseat blowjobs, guys fingering me, missionary style fucks, stuff like that.” “Have you ever had a guy give you head? Lick your pussy? Suck on your clit? Fingerfuck your cunt or your asshole?” “Oh, gosh no. Well, I’ve had guys finger my pussy but none of the other things.” All this time she had been gulping her drink as I gave my answers. Her eyes showed that the booze was taking effect. “Have you ever played with yourself? Ever tried a dildo or vibrator?” “Fuck no!!” she said almost indignantly. “Why would I do that?” “Because it feels good.”
“Why don’t you try playing with your pussy now? I’d love to watch.” She looked at my crotch and saw my bulge again. Then she leaned back some and tentatively reached down to her crotch. I could see her fingers rub up and down on her slit, eventually parting it. It was glistening wet, and she rubbed her fingers up and down smearing the thick juice around. “Now feel up towards the top. You’ll find your clit.” She moved her hand about, then suddenly let out a gasp, then Ooohhhh. She had found it! Seeing an opportunity, I started stroking her inner thigh as she continued to explore her newfound friend.
As the moans got louder, I said, “Here. Let me help.” I pulled her down until she was lying flat, her legs bent at the knees. I struggled a bit but succeeded in getting her mini-skirt up and out of the way. I slid my hands under her butt, lifted up, and put my face in her crotch. Her smell was amazing. Sweet yet pungent, almost like a virgin. I gently began licking her cunt, purposely avoiding her clit. At least for now. I licked her wet pussy, swallowing her sweet nectar. I did my best to tongue fuck her pussy, but the angle wasn’t right. So, I then attacked her clit. When I first wrapped my lips around it, she let out a loud gasp. “Oh my God! That feels so fucking good! I’ve never felt anything like that before.” I continued to work my magic on her clit, sucking it in and out, running my tongue around and around it, licking it up and down, back to sucking it. She was obviously enjoying this, and her moans and groans got louder and more frequent. Finally, I slipped a finger into her pussy hole, stroked it a few times, then put a second finger in.
Now I was full on hard play with my mouth on her clit and fingerfucking the shit out of her cunt. She began rocking her hips and moaning loudly. I quickened the pace of my fingerfucking, now using three fingers. I was ramming my fingers up her twat when suddenly she stiffened up, screamed out “OH SHIT!!” and then her pussy got really wet. She shuddered and was panting, trying to catch her breath. “Holy fuck! That was amazing. I’ve never had an orgasm before if that’s what that was. No wonder people have sex.” “Ah, my sweet little summer’s child. You ain’t seen nothing yet. Wanna try a blowjob? Learn how it’s done properly?” “I guess so. I’m kinda nervous but I want to learn. Let me get another drink first.”
As she poured drinks, I got my pants off and started stroking my cock, still hard from what just happened. When she returned, I sat back normally on the couch and told her to get on her knees between my legs. She took a couple of giant swigs of her drink and kneeled in front of my cock. “Now, before you begin, take a good look at it. Take it in your fingers and examine it. See the top part is the head. The long part is the shaft. Look underneath on the bottom side. See that area just below the head and above where the shaft starts? Well, that’s my clit. It’s as sensitive and feels just as good as your clit. You need to find it and pay attention to it whether it’s with your fingers or your tongue. Very important. And, once you learn to control your gag reflex and can take the whole enchilada down your throat, the muscles at the back of your throat rub on that clit area, producing amazing feelings. Think you’re ready?” “I guess so” she said as she took another deep draw on her drink.
Finally, she put her lips on my dick and started fumbling around. She took an inch or so into her mouth and explored with her tongue. She was a beginner, so I took my time. “Gently, slowly, start stroking it in and out of your mouth. Try to take more of it in with each stroke. Imagine that it’s like a guy stroking his cock in and out of your pussy, only it’s your mouth; like you’re fucking him with your mouth. And keep your mouth wet. The wetter and sloppier the better. Don’t worry about drooling spit. It’s all part of the fun.”
She started bobbing her head up and down trying to go deeper each time. Once she went a bit too far and pulled up, gagging and coughing, spit running down her chin. But I put my hand on the back of her head and pushed it back down on my cock. She went right back to it, now swirling her tongue across my clit as she got better and more confident. Soon she got a rhythm going and was taking most of my shaft in with each stroke, going to the back of her throat but no farther. “OK. Now for the fun part” I said as I stood up.
“So far you’ve been fucking my cock with your mouth. Now I get to fuck your mouth with my dick.” Her soft brown eyes looked up at me with some fear and hesitation. “Don’t worry, honey. I won’t hurt you. Just gonna show you what my mermaid needs to know.” I grabbed my dick and guided it into her wet mouth. She opened and I slid my erect shaft into that warm hole. I grabbed her head with both hands and started pumping my rod in and out, keeping it kinda shallow at first. I was pumping slowly and soon began to push it deeper until I found the bottom. I continued to stroke, knocking at her deepthroat door with every stroke. I started giving her encouragement.
“That’s it, honey. Just let me fuck your mouth slow and gentle. Relax and keep your mouth wide open. You’re doing great and it feels so damn good.” I continued knocking at the back of her throat. “I love fucking your mouth. It’s so warm and wet. I just need you to be my little mouth whore for a bit. Show me that you wanna suck my cock. Take that face fuck you slut. Just relax your mouth and your throat. Relax honey. You’re doing fine as my little mouth whore.” I could feel her relax a bit, especially her throat.
My cock was sliding in and out slowly and gently, pressing harder and harder at the back with each stroke. Finally, I felt her throat open just enough so I forced my cock all the way in past her back door. Before she could gag and react, I pulled it back and jammed it in again, holding her head hard against my groin, my entire cock deep in her throat. I held it there for just a second or two, as her gag reflex caused her belly to heave. Then I pulled it out and released her head. She came up sputtering and gagging. She coughed and gagged, and gobs of spit drooled down her chin, but she didn’t puke. I sensed that she had had enough but I was crazy to cum. Before she could move, I grabbed her hair, pulled her head back and started jacking off, my cock aimed at her face. Within just 10 or 15 strokes I shot my wad on her pretty face. My creamy jism squirted out randomly from her hair to her chin. I slapped her face with my cock and smeared my cum around ending at her mouth. I pulled her head forward, forcing my dick to part her lips and slip once again into her luscious wet mouth.
“Congratulations! Your first deepthroat!! You didn’t puke so you get an A+. And next time you’ll learn what it’s like to have that cock shoot it’s load when it’s deep down your throat. Women have told me that they can feel the dick spasms when he’s cumming, in their throat muscles. Most of them love that sensation. A real win-win if you ask me. What’d you think?” She coughed some more as she wiped the spit off her chin and sucked on her drink. She looked at me with her soft brown eyes, filled with satisfaction and in the feeblest, softest, whispered voice she answered, “I liked it.”