Those Autofellatio Blues

If you knew the exact day you were going to die, would you be able to function? Could you go about the normal, humdrum minutiae of life knowing the precise date of your demise? Even if you had 80 years ahead of you, would you wake up thinking, "Well, I only get to do that 29,000 more times,"?

I bring this terrifying dilemma to your attention because, as death is one of the defining aspects of life, so is sex, and I happened to know the exact date that I would lose my virginity. It was going to be on Thursday, as a matter of fact. I'd hoped that Elaine's would be the first pussy I would enjoy, but her gorgeous and scary friend Julia demanded that she be the first to enjoy my freakishly large penis. Elaine acquiesced to her wishes. And Thursday was the day.

I insisted on one condition-Elaine had to be there. At the party where I'd first encountered Julia she had butt-fucked me with a strap-on until I was in tears. I was afraid that during the emotionally vulnerable moment when I lost my virginity Julia would do something vicious and twisted that would fuck me up for life. I trusted and loved Elaine, and knew she wouldn't let me get fucked any other way than the way God intended. If, indeed, God had a hand in this rather messed-up situation. I kinda doubt it.

I was excited, sure. To finally have my penis inside a woman, to bury myself inside a warm, wet vagina...it had me climbing the walls. I loved getting soapy handjobs and enthusiastic blowjobs, but pussy was of course the Holy Grail. Like most guys I'd given myself handjobs. Unlike most guys, I'd given myself blowjobs. But no guy can enjoy pussy without a woman. Unless the guy...well, best not to even think about that. Yuck.

The woman I was going to fuck was incredibly gorgeous, incredibly sexy, and incredibly scary. I guess two out of three ain't bad. Julia demanded that I abstain from sex until the Big Day, and I tried, but it was impossible. On Monday I woke up at 3AM with a hard-on nearly scraping the ceiling. I padded silently to the door and locked it, ensuring that my Mom couldn't blunder in on me as she had several weeks before. I lay on my back and flipped my legs over my head and wedged them in that gap in my headboard. It was harder than usual, I had some trouble tucking myself in a tight enough ball to get my cock to my lips. Out of practice, maybe.

My mouth was absolutely watering, and I used some of that saliva to get my head nice and wet. I knew from experience that nothing helps transmit every loving touch of your lips and tongue through your cock like a sloppy wet head. Once I was wet enough I wrapped my lips around the fat bulb and started to suck. I was already leaking pre-come from my spigot and the taste made me redouble my efforts.

I sucked, and I sucked, and I sucked. I had to come soon both because I desperately needed the release and because my stomach muscles were starting to tremble with fatigue.

"Umm, oh, mmmph!" I moaned as my lips and tongue brought me to a glorious orgasm. I greedily swallowed every drop of my runny load. It felt so good to have the Cloroxy taste of my come in my mouth again. It had been quite awhile since I'd given myself oral pleasure, and even if it was far, far better to have a woman suck my dick, there's something about taking care of yourself that's oddly satisfying. I belched quietly and went back to sleep.

I had even better things to look forward to the next day. I went to visit Elaine with a bright idea. "I want to lose my virginity with you," I said. "Please, let's do it now, and that way I won't be so scared with Julia. She'll never know."

Elaine, her dark red hair pulled up in a matronly bun, smiled but shook her head. "No, honey. You promised your cherry to Julia, and you should keep your promises." She touched my cheek in her motherly way. "And you don't need to worry about having sex with Julia."

"I don't?"

"Of course not. You'll see, sex is the most natural thing two people can enjoy together." Then her smile twisted mischievously. "What you need to worry about is Julia afterwards."

I didn't like the sound of that. "What do you mean?"

"I love Julia, really, but she is a bit of a strange duck."

Calling Julia a "strange duck" seemed a good candidate for Understatement of the Year. "What would she do?"

She laughed. "Who knows? She might try to enslave you, she might crawl after you screaming that she loves you and will kill any woman who looks at you. Her emotions tend to run all over the place."

"Oh, that sounds great," I said, my stomach really starting to churn. "I'm not going through with this."

Elaine's smile vanished. "Oh, you don't want to do that. No, no, no. Julia doesn't handle rejection well. At all. You don't want to do that."

"I'm afraid," I said, and Elaine came over and hugged me, pillowing my head on her big, soft breasts. "Don't worry," she said. "Just enjoy yourself, have sex with her, and everything will be fine."

A simple enough solution. Have sex. Sure. I let my head rest against Elaine's breasts, enjoying their warm, powdery scent. Elaine's hand moved from my shoulder down to my groin. "I'm not sure how Julia will react to getting fucked by this big..." she unbuttoned my shorts, "thick..." she pulled them down to my ankles, "cock." She wrapped her fingers around my shaft and started pumping slowly. I sighed with delight as she used her long fingernails to tickle my testicles. Playful lust brightened her dark brown eyes.

"Let's go upstairs," I groaned. Upstairs was Elaine's "fun room", where she had a battery of dildos and restraints and a bed that had cuffs attached to a winch, a bed that helped me fold myself in two.

"You don't like the way I suck your cock?" Elaine teased.

"Let's suck it together," I panted.

She took me to the room and put me in the stirrups and cranked my legs back over my head. It wasn't as uncomfortable as the night before but it was still a bit of a strain. But my dick was right in my face, and I opened my mouth and the silky smooth head slipped between my lips. I used my tongue to bathe my cockhead in spit as I watched Elaine pull the pins holding her hair up and drop them on a small table. She shook her hair free and it fell in thick waves about her shoulders. She walked over to a big dresser and pulled open a drawer. "Maybe a toy, for fun?"

I gently gnawed on my knob for a few delicious seconds before I felt Elaine's fingers gliding around my anus, leaving behind a thick layer of lubricating gel. I knew what was coming next and I groaned around the big meaty stick in my mouth. Elaine inserted a thin stainless steel dildo deep inside me, it wasn't thick but it was very long.

"You like that, huh?" she said.

"Uhh!"

"How about this?" She twisted the end and the probe began vibrating gently inside me. My mouth released its hold on my cock long enough to whimper, "Oh, Jesus."

"Can I have a taste?" Elaine asked. She knelt next to my head and leaned down and wrapped her lips around my throbbing shaft. She was so close I could smell her soft red hair. The dildo hummed inside my rectum and Elaine's lips and tongue ravaged my vulnerable penis.

"I'm gonna come!" I moaned.

She drew her slavering lips away from my cock. "Not just yet." She fed my cock back into my mouth, let me suck myself for a few spine-melting strokes, and then she took her turn, bobbing her own warm lips up and down my length. It was an awkward position for her but she didn't seem to mind. The frantic expression on my face told her how much pleasure she was giving me.

"You can have it, if you want," I said as my nerve cells started to fire all at once. "I had a big load last night." I knew Elaine loved swallowing my semen as much as I did. She pulled her lips away long enough to say, "Are you sure?"

"Just save me a taste."

Elaine smiled and forced my cockhead through her pursed lips. The slippery friction drove me over the edge. She sucked it and her nails tickled my balls and the dildo buzzed away and I moaned with joy. I ejaculated and my cock spurted and shook and hot, sticky semen poured down Elaine's throat.

"Oh my God that's good," Elaine said with an unusual amount of emotion. She daintily cleaned my penis with her tongue. "I can't wait to feel that thing go off like that inside me. Feeling you shoot inside me alone would be enough to make me come."

"Then let's do it now," I said. I wasn't quite hard enough yet but I knew in about ten minutes I would be raring to go.

She kissed me on the lips, her tongue gently moving inside my mouth, giving me that taste of my come that I wanted. She kissed me for a minute, and then I pulled my face to the side.

"What's wrong, honey?" she said.

"Lower me," I gasped. "My abs are cramping."

Elaine brought me back to a prone position and I panted with relief. "That never happened before," she said.

"That's because you've been chaining me to the walls and stuff like that. I'm out of shape."

"Well, rest your stomach muscles. You'll be using them on Thursday.

*****

School that day was torture. My friends irritated me, my teachers bored me, and Bridget Landau, the uber-hottie who ruled our school, wore this jailbait plaid jumper with knee-high socks that made me throb so much I thought there wasn't enough blood flowing to my brain to keep me conscious. She was so incredibly juicy and succulent I almost excused myself so I could go to the bathroom and jerk off.

If I had, I would have had company. My friend Vince said, "Can you believe what she wore today? Jesus Christ. I thought we had a fucking dress code."

Dave said, "What, you wanna be the one to tell her to change?"

"I can't concentrate! She drives me crazy! You'd think one of the teachers would say something to her."

"They're more afraid of her than we are," Dave said.

Bridget did inspire fear as well as lust. I wondered how any man could ever measure up to her standards. I wondered if she was lonely, so isolated by her relentless sexiness that she couldn't have an enjoyable relationship with a man. Then again, she was also the most unpleasant, stuck-up and arrogant person I'd ever met, so who cared if she was miserable? Fuck her, she deserved it.

The day, at last, came to an end. I rushed home, blitzed through my homework, and told my mom I was going "out". She knew where I was going, since she had, after all, put me in Elaine's tender care. Still, knowing that her son was going off to get diddled wasn't cause for cartwheels.

"What are you going to do when you go away to college?" she asked. "You won't be able to bother Elaine every day."

"I'll cross that bridge when I come to it," I said blithely as I skipped outside to the car. I couldn't be bothered with thoughts of the future when my present was fraught with such import. I was going to pop my cherry!

I pulled into the driveway to find another car already there. Julia's. My hands were shaking Elaine greeted me with a hug and a kiss on the lips. "Are you excited?"

I put her hands on my crotch. "What do you think?"

She bit her lower lip. "Oh my."

"Is she here?"

Elaine nodded, still staring at my groin. Her fingers traced the outline of my cock. "I'll take you to her."

She took me to the "Fun Room", and there she was, the woman who would be my first lover. Her lustrous dark hair was pulled back in a long ponytail, her lips were painted a vivid red, and she wore a black silk teddy that accented every curve of her voluptuous body. Dressed to kill. I involuntarily licked my lips as I looked her over.

She leapt up from the bed and shrieked, "My cock is here!" She grabbed my zipper and yanked. I looked at Elaine in terror as Julia tore at my clothes with her talons.

"I guess you're glad to see me," I said meekly.

She pulled out my cock and, without further preamble, capped her mouth over my cock. Her eyes bored into mine as I watched my giant erection stretch her painted lips into a wide O. Then she stopped. "Why should I do all the work? Make yourself hard. I want to watch."

I knew what she meant. Elaine helped me get in the stirrups, and the wheel went clank-clank-clank until my skinny body was folded in half and my penis loomed like a pink torpedo in my face.

Julia sat on the edge of the bed and spread her legs. Her long nails played at the edges of her black silk panties as she watched me give myself head. "Suck it," she hissed.

I soon replaced her saliva with mine coating my dick. "Mmm! Mmm!" I moaned as I blew myself. I didn't know if she wanted me to come in my mouth, and I let myself go for a moment. I closed my eyes and felt the lava begin to build inside me. Then I felt fingernails fondling my ass, my testicles, and finally they closed around my shaft. I opened my eyes and Julia was staring at my erection with awe. "Should I come?" I gurgled.

"No! I want you as hard as possible and your balls as full as possible. Are you about to come?

"Yes!" I groaned, engulfing my cock again with my mouth.

The winch suddenly started clattering, and my legs gradually lowered back to the bed. I sucked my cock as long as possible, but eventually my slavering lips lost contact with my quivering prick. Elaine unshackled me and then stepped aside for Julia, who had removed the teddy and panties. She was so gorgeous, so hot and sexy, I couldn't imagine why a woman like that would want anything to do with a skinny kid like me. I couldn't decide what to look at first, her cruel, smiling lips, her firm, round breasts, or the dark thatch between her legs.

Julia, however, only had eyes for the big pink thing sticking up between my legs. "Get up," she commanded, and I obeyed. She lay down on the bed and spread her legs wide. "Come on, come on, give me that big fucking cock!"

Elaine stood next to me and tore open a foil package containing an extra-large condom. She daintily rolled it down the length of my phallus. "Now, go slow at first," Elaine said, grabbing my lubricated shaft and guiding me toward Julia's wide-open legs.

Julia said, "Fuck that, put it in me and start pounding."

"He's really big, Julia. He might take some getting used to."

Julia's laugh was a hoarse bark. "We'll see. Come on, I wanna fuck!"

I'd dreamed about this moment since I popped my first boner. Having a gorgeous older woman demand my dick was just about my favorite fantasy. The reality, though, wasn't quite so pleasant. I was scared shitless. I knelt between Julia's legs and Elaine aimed my cock at Julia's pussy. Her opening looked so small compared to my big stick. Elaine rubbed my cockhead up and down Julia's slot, and then I caught in her hole. "Slow," Elaine said, her hand on my buttocks, pushing me.

I guess I expected my cock to sizzle with her heat, expected the sensation to be so intense it would overwhelm me. It wasn't like that. It was tight and snug and warm and slick, but I could handle it. The condom may have helped dull the sensation, but I knew that I wouldn't come in two seconds. That gave me a bit more confidence.

Julia's reaction helped as well. "Holy fucking shit, he's big," she whimpered. "I can feel every vein in his cock." I pulled my hips back and thrust back inside her. Julia groaned. "Elaine...he's huge!"

Elaine pulled my hips, drawing me out, and then she pushed me back in a bit deeper. I exhaled hard. That felt really good. I moved in and out again. It felt really, really good. Wet and tight and the wetness and tightness was all around me. I started thrusting slowly, Elaine's hands still on my hips, not letting go, as though this was my first time riding a bike without training wheels. In and out, in and out. I looked down and saw my huge tool stretching Julia's opening, her labia caressing my shaft with every stroke.

"Sweet Jesus!" Julia cried. She wasn't the arrogant, selfish harpy who fucked me up the ass with such gleeful cruelty. Now I had the power, my cock placing her in my control. I started fucking her faster, deeper, and it felt better and better. The feeling of penetrating her was magnificent, the thrusting of my hips the most natural motion in the world.

I put my hands on Julia's thighs and started fucking her. Elaine released her hold on my hips and I was pedaling on my own. Julia was so wet that my every thrust made a sexy, sloppy sound. I introduced myself deeper and deeper inside her, until I was buried to the root with every stroke. Her nipples suddenly flushed deep red and tightened into hard plugs, and I busied my thumbs with fondling them. She moaned even louder and she started to sweat all over, a thin sheen of perspiration making her lush body glisten.

"Elaine, oh God, oh God, he's so fucking good!"

I was getting payback and I loved it. I fucked her a little harder.

"Oh shit, I'm coming! I'm coming, I'm coming, huhhh!" Her voice broke off and her bright red lips formed a twisted grimace. Her nipples were so hard I thought they might pop off like rivets under too much pressure. She quivered from head to toe as her orgasm exploded inside her, and I kept fucking her through it all. I remembered how Julia had fucked me up the ass and it gave me extra incentive to show my newfound dominance.

"That's right," I said, "you're my bitch, you're my bitch..."

I shouldn't have been so cocky. As she came her pussy kept quivering and spasming in wonderful rhythmic contractions and one of those frantic squeezes got me in just the right place. That fast, I was about to come. Now it was my turn to moan and shiver. I turned to Elaine and looked at her with beseeching eyes. "I'm gonna come," I whispered in a lost little boy voice. As though she could do something about it.

"Come, honey," Elaine cooed, putting her hand on my buttocks and spurring me on. I thrust faster and faster and faster and Julia gasped and writhed underneath me. The pressure built remorselessly inside my cock every second, until I hit that wonderful point of no return.

Julia was shrieking now. "Oh shit, you're fucking killing me! Fuck me!" I pistoned myself faster and faster, the delicious pressure building every second, until I hit that terrible point of no return.

Julia was shrieking now, "Shit, you're fucking killing me! Fuck me!" I thrust myself inside her on last time, so deep our pubic hair rustled together, and then the golden sunrise of my first orgasm inside a woman burst over the horizon. My semen flooded the reservoir tip of the condom and jolt after jolt of electric pleasure coursed through my body.

Julia arched her back, forcing me as deep as possible inside her. "It's twitching inside me," she groaned. She was wheezing, taking long, ragged breaths. Her eyes were shut tight. When they opened they were spacy, unfocused, dreamy.

"That was the best cock I've ever had," she said to Elaine, as though I wasn't even there, as though my penis was the only part of me that mattered. "It's not just huge. The shape, it's perfect. It's curved just the right way to hit all your hot spots. It's fucking incredible."

She put her hands over her eyes. "I haven't been fucked like that since Bill Payton stopped swinging with us."

I jerked up, sliding my cock partway out of Julia, who groaned, "No, no, stay inside me!" She wrapped her legs around my waist and shoved me back in. I looked at Elaine, who held a single finger to her lips. Julia rubbed her eyes for another few seconds, then those hawk eyes focused on me. "You just went soft all of a sudden. What the fuck's wrong?"

"Nothing," I stuttered. Elaine came over and put her hands on my hips. She said, "I'm sure he's just a bit in shock about what he's just done."

"Oh, yeah," I mumbled. Elaine unlocked Julia's legs from my waist and slowly eased me out of her pussy. Julia moaned in protest and I extracted myself inch by inch. It was a relief to finally be disconnected from her. Elaine removed the condom, filled like an éclair with my cream, and carried it to the bathroom to throw it away.