This is a story I wrote so I could more fully explore the depths love for my penis. It's roughly based on stories young coworkers would tell every Monday morning describing their libidinous adventures over the weekend. I embellished their tales and provided them for their reading enjoyment. They encouraged me to publish, so here they are. Selfishly, I got to cum about twice per chapter while writing it! The pages are probably still a little sticky--sorry. Please write; I love feedback: brad_rent@yahoo.com.
Oh yeah... and please make a contribution to Nifty.org to make sure these and other stories keep being published—and I get to keep cumming!
Chapter 3- Final Preparations
Lily drove down to stay on my boat the night before we left for Fort Lauderdale. Discussing our plans over the phone for the last few days got us both hot to explore different kinds of sex as individuals as well as our mutual sexual growth as a couple. As a side note, these frank discussions led to some pretty heated, erotic phone sex in the days before driving down; both she and I experienced our first `phone-gasms' while fantasizing about trying to get something going with the staff in the ship's spa or elsewhere. If you've never masturbated while talking with someone else who's also masturbating on a phone; try it sometime- - it's life changing!
Lily's fantasy involved having her female masseuse meet for a private, both-naked' massage in our cabin, with me openly masturbating while watching Lily and her have sex afterward- - and them watching me pleasure myself. After they bring each other off with a mutual cunt-suck, Lily's fantasy continues with me lying on my back fucking her reverse cowgirl style.' While the masseuse licks and sucks Lily's cunt from the front- - as well as my balls and base of my buried dick- - she orgasms on my buried cock again and again. After she's cum two or more times, her fantasy allows for me to shoot my load up inside her and then slide out.
After the masseuse cleans my still-hard penis of our combined juices, she slurps up my load as it gushes out of Lily's hot, quivering cunt, then shares that tasty goo via wet, sloppy kisses with both Lily and me. I told her that it all sounded ok with me (except maybe the `me-eating-my-own-sperm-out-of-their-mouths' part), but she needed to remember that once I stuck my dick in her cunt- - from behind especially- - I wasn't going to be able to outlast her while she comes multiple times. She acknowledged that as a sad fact, but said it still wasn't going to ruin her perfectly good fantasy. "You just stay hard- - like we practiced- - and I'll take care of the rest."
I should explain Lily's reference to `like we practiced.' Soon after we started dating, she took on the challenge of expanding my sexual awareness of my own body. Sure, I'd been jacking off for years, but was amazed at what I didn't know about my own body. Over the ensuing weeks, she patiently worked on me on many occasions. Let me describe our first session.
As most couples do, we initially passed through the usual repertoire of exploring each other's sexual preferences- - you know, passionate kissing, tit-and-package squeezing, stinky finger, jacking, nipple sucking, blow jobs, eating pussy; followed shortly thereafter by fucking regularly in all types of positions- - by the way, her favorite seemed to be doggie-style like I described earlier, with me on my back, her sitting up straddling me and hanging onto my balls. Later, she progressed to also diddling my hole while she jumped up and down on my cock, but at first, not so much.
Lily had an incredible, tiny pussy that would squeeze my cock just like a tight fist. The first time I entered her juicy snatch, I came after about eight seconds. Thank God I was young; after a short break, we began a second course without even pulling out. This time I lasted about 5 minutes, allowing her to come while I thrust in and out. Overall, I shot what seemed like half a cup of cum in her sweet little cunt; by the time I pulled out, we were drenched with both of our juices.
After a few more of these straight' fucks, Lily began having what she called training sessions,' where she said she wanted us to work on a few things' and try out some new stuff.'
"Are you game, Trav?
"'Work on' and `try out' what, exactly"? I asked suspiciously.
"Things like you lasting longer, coming harder in or on more places, and going more than two rounds before you're done."
I couldn't think of a downside to these lofty goals but wondered what more places' meant, so I just said, guardedly, "OK. I'm up for that." (See what I did there... up' for that?)
"Not so fast," she added, "there'll be some stuff for me, too."
"Like what?" I asked.
"Like toys..." she trailed off.
"And what else?" I asked.
"And ass play," she added.
Thinking I'd like nothing better than to fuck this sweet thing in the ass, I wholeheartedly said "OK! Why was that so hard?" (See... I did it again... `hard'? What a clever writer)
"I don't just mean fucking in the ass... I mean licking and fingering and putting stuff up my ass... and, um..." there was that pause again.
"And what?"
"And me licking, fingering and using toys in your ass, too." She added with a gleam in her eye. When I just stared at her without answering, she added "Turnabout's fair play and, besides... I think you'll like it!"
After remembering all marvelous sex we'd had up `til now- - all thought up by this talented vixen- - I paused, then offered "OK, we'll see. Where do we start?"
"Next time I get to drive the train- - that'll be our first session. You'll see."
Sure enough, the next weekend I drove to her apartment; soon we were at each other. We'd just started when Lily broke off our long kiss and told me to strip. She stood there- - fully clothed- - and watched as I took off my T-shirt, dropped my shorts and slipped off my tightie-whities. By the way, Lily got me to switch to jockeys early on in our relationship... she thought everything down there `just looked better' encased by tight white cloth. "I can see all of your man parts better in these," she said, cupping and squeezing my growing bulge. I will admit I've come to prefer the tightness around my ass and balls that my jockeys provide and boxers just didn't. My cock always stirs to half-chub whenever she stares at my crotch or remarks about how nice my junk looks in my tight underwear.
This time, however, she had me strip naked before proceeding.
Grasping my boner, Lily pulled me like a wagon behind her and headed for the bathroom.
"I'm going to teach you how to clean yourself out... have you ever had an enema?
Blank stare.
"OK... just do what I say...
I was sort of in a daze at first- - but more than a little intrigued- - she had me prop one foot on the edge of the tub. After filling a large rubber `bottle' with warm water, she parted my butt-cheeks with one hand and worked a long hose up into my hole.
My God!
"I'm now going to turn a valve and all this water is going to drain up into your rectum... you need to clench to keep it from coming out, OK? When we're all done, you'll be ready for anything!
The sensation of the warm water filling me up was both uncomfortable and kinky and I forgot about asking her what `anything' meant; after a minute or two, she said, "OK, now I'm gonna pull the hose out and you're going to jump up and down a couple times- - don't let anything leak out of your ass...
I felt like a fool jumping up and down with my boner alternately slapping against my leg, then whacking against my stomach.
"Now sit down on the toilet and let it all out.
I complied. I won't describe everything that happened then; suffice it to say that if you haven't ever had an enema, you ought to try! It, too, is life changing! And apparently leaves you ready for anything!
"Now stand up and put your leg on the tub again... one more time ought to do it.
And it did. As I `let go' a second time, only the warm water came out.
Grasping me by my still-hard penis once more, she led me back to the living room.
Next- - her still fully clothed-- Lily dropped to her knees behind me and mumbled, more to herself than me, "What a great ass you have," while softly running her nails all around my naked butt cheeks and up and down my legs. I'd been fairly hard throughout the whole enema thing, but all this extra attention to my whole butt region got me rock hard instantly. Her soft feathery caresses gave me goose-bumps, especially when those long nails gently moved up and down the full length of my crack. She had never shown much interest in my ass, so it was a little bit kinky as she kneaded my butt and rubbed all around the upper part of my thighs.
"Spread your legs wider so I can see all of you," she directed.
"That's it... now bend over so I can see everything. What a spectacular view!"
Lily reached underneath, between my legs to jack my thick, pulsing cock and squeeze my fat nut-sack. I looked back between my legs to see her gazing up at my dick, balls and puckered hole from behind. She gathered my cock and nuts into both hands and squeezed them together. Moving her face forward, she stuck out her tongue and licked my balls. "I love your musky man smell," she said nuzzling the side of my bulging scrotum. She took one, then the other testicle into her hot mouth and sucked noisily. Pulling away, my nut-sack was now slick with her saliva.
I nearly left the ground when she started in again; but this time, licked from the base of my balls, up my chod and all the way up the full length of my ass crack. Each time she passed by my sensitive hole, I flinched.
"Relax," she said. "I told you you'd like this." The next time she lingered at my anus and the licking changed to jabbing with her pointed tongue. Tingles shot up my spine and my cock quivered when she pushed her tongue against my puckered hole again and again- - all the while squeezing my cock and balls together.
"That feels awesome," I moaned, "I never thought anything could feel that good."
She responded by jabbing her tongue against my opening again and again. She had released my cock and was now squeezing and kneading just my aching, slick balls.
My hard-on wagged free in front and I couldn't help but clench, which released a large gush of pre-cum out the tip. The clear bead hung there momentarily, then as more oozed out, left a long, clear thread of `drool' that reached nearly to the floor.
"I can't take much more of that," I said. She giggled and stood up.
"I knew you'd like it," She said confidently. "Here... stand up."
Taking my hand, she led me to a chair in the living room. "Just sit there and do what I say." She then slowly stripped off her own clothes, down to her cute, red lace bikini panties, while I hungrily watched her reveal her beautiful, tight body. Those spectacular tits swayed and their nipples hardened slightly when she pulled off her matching bra.
Stepping to my chair, she fed me one of her tits and I hungrily slurped and nibbled the leathery nipple until it was standing tall. Meanwhile I'd been squeezing the other tit and pinching it's nipple to equal hardness. With my other hand, I was rubbing her crotch through her panties and her shudder told me I was doing it right.
Backing away from the chair, she kneeled down again and said "Jack your cock for me, Travis... jack it `til it's big and hard... that's it, stroke it... use that pre-cum to make the head all slimy... good job... rub it all around... now squeeze your fat balls while I play with my tits for you. I know you like to watch me do myself... go ahead and jack off for me... I love to watch you masturbate, too- - but don't cum yet... I want to learn how you pleasure yourself while I do myself."
I'm not so sure there was much to learn... I was pretty good at stroking it until cum squirted out the end... and it wasn't going to be long now, I was so turned on. Watching her watch me while both of us worked our own crotches, though, was way past anything I'd experienced before.
I could tell that the hand buried in her panties was busy fucking a finger or two in and out of her tight, sweet cunt. Her eyes glazed over and her mouth parted slightly, her breath coming in short gasps while she sluiced in and out of herself.
I was getting closer to coming. She must have sensed that when she again said, "Don't come yet... I want to eat your sperm- - but I want you to watch me get off first." I slowed down my stroking and took it all in while I squeezed my cum-swollen balls in my other fist.
She was magnificent- - her skin was flushed and her tits quivered while she sawed away at her pussy for what seemed like minutes.
Her eyes rolled back in her head and I could tell she was finally coming. She reached around and buried her other hand in her panties in back. "I have a finger in my cunt and one in my ass right now, Trav... someday I want both holes filled with thick, hard cocks." I couldn't tell if this was a fantasy or a goal- - at that moment I guess I didn't care- - I just hoped my cock was one of the two she was talking about.
Or maybe she meant she'd suck me while having two other cocks in her at the same time. This was probably not the right time to ask, but knowing Lily, I was sure we'd talk about it later and I'd have my answer.
Her orgasm rocked her to the core... to this day, I don't think there's anything as magnificent as a woman on her knees in front of my hard dick quivering and shaking as her naked body is racked with orgasm! Again and again she plunged her fingers into her holes; her guttural moans marked the beginning and end of her long, drawn-out orgasm. It was hard for me not to go over the edge with her and paint her beautiful face and tits with rope after rope of my squirting jizz while she quivered, moaned and bucked through her own cum. As she came back down to earth, her skin was still flushed but her breathing slowed to near normal.
When she was at last ready for me to join her, she said "Lean way back and slouch in the chair for me... I want your cock and balls closer," she said. "Put your legs up over the arms of the chair so I can see your whole crotch... that's it... man, I wish I had a dick right now; I'd shove it so deep in you!
I was glad just then that she did not have a dick- - maybe someday, but not today- - I complied and slunk down, then swung my legs onto the arms of the recliner, my whole ass hanging over the edge.
While she continued languorously fucking her fingers in and out of both holes, she leaned in and sucked one of my balls into her mouth. Each time I jacked my prick, it stretched the skin of my nut-sack and made the sensation of her sucking all the more intense. Then she moved to my other nut; I was getting close to shooting my load. I moaned as she released my second ball, then went straight for my vulnerable anus, now more exposed than ever with my legs spread wide apart.
"We need to get you a ring or a strap," she said mostly to herself. "That'll pull your fat nuts up out of the way so I can attack your hole more easily." I twitched at that visual!
Without some device to keep them pulled up, she brought a hand out of one of her holes and used it to push my balls up and re-attack my winking pucker.
She started in again with her hard tongue probing my tingly opening. Again and again she pushed against the tight brown ring. She managed to get her tongue inside my anus on her third or fourth lunge and the sensation was the most intense ever. When I thought I was within a stroke or two of coming, she backed off, leaving me panting and groaning.
Lily pulled her hand out of her other hole with an audible `pop' and grabbed my raging cock. She jacked my dick with her slick hand but left her other wrapped tightly around the base of my balls. Before I knew what was happening, she took my dick into her hot mouth almost to the root. She had never tried to take all of my cock at once, but here I was ball-deep in her hot mouth- - I must have been halfway down her throat as well, I was so hard. She pulled off, looked up into my eyes and said "I love the taste of your cock... I want your goo in my mouth... all of it... now!" Back down on my cock she went- - again, all the way to the base.
At the same moment, she released my nuts and jammed a finger about an inch up into my anus! It felt awesome and triggered my cum mechanism. I don't even think I lasted that first eight seconds. Blast after blast of my hot jizz shot into her mouth while she swallowed hungrily without missing a stroke. I'd never felt a sensation as intense as this- - my over-stretched cock as deep in her sweet mouth as I'd ever been while my asshole was clenching and spasming on her wet finger. I couldn't talk... I could barely breathe as I groaned and emptied myself into her hot, sucking mouth.
She kept my spewing dick in her mouth, but pulled her finger out of my hole and put it back in her own. Almost immediately, she started shaking and quivering to a second massive orgasm that consumed her whole body. I was a little afraid she'd bite my cock off from her second all-consuming spasm, but she gently sucked the last drops of come from the head of my dick as her own orgasm subsided.
She left my cock in her mouth but slowed her sucking movements to a gentle tongue bath all around my cock and balls.
After a few moments, she said "So much for the foreplay--now we fuck," she said. And fuck we did!