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.
