Now or Never

Neither of us planned it that way, but my most beautiful friend got fucked by two different guys with enormous dicks, once when she was just 18 and once seven years later — and I got to watch both times!

It all started when Becky and I were freshman and decided to join the same sorority. We were each assigned a different “initiation project.” The girls concocted a rather interesting assignment for Rebecca, because she seemed so innocent, even for a freshman. They demanded that she try to seduce this grad student named Neil, sleep with him, and bring them back the used condom — all by sunset . And, they told me to hide and watch the action, to verify that the sperm came from the designated “donor”!

The sisters chose Neil for some specific reasons: Laura, one of the upperclassmen from Alpha Chi Omega, worked as a cashier in a pharmacy near campus, and she sometimes reported back to the sorority when some poor slob made a particularly embarrassing purchase. Apparently, she had occasionally staffed the cash register when this guy Neil bought packages of those “Trojan Magnum XL” extra-large condoms. He was all shy about buying them and never made eye contact at the point of sale. But, Laura wrote down his name from his credit card, eagerly figured out who he was, and then saved him for Rebecca’s initiation.

Now, the challenging part was that Neil had a steady girlfriend, was quite a bit older and, as I said, didn’t have the personality (or the looks) of your stereotypical stud. Plus, Becky herself didn’t exactly have a lot of experience in tempting random strangers for quick sex. She even confided in me that she’d only slept with a few guys in high school, none with really big cocks. But, she really wanted to join Alpha, and, with no time to lose, she immediately set out to nail Neil.

Her best weapons were her natural good looks and body. To help her all I could, I sped her to the local mall to buy some lingerie. Besides that, she wore her tightest jeans and tiniest T-shirt. Then, she walked towards the classroom where we knew Neil would be at that time. I wished her luck, went back to her bedroom, and waited.

After what seemed like forever crouching in Becky’s closet, I finally heard the bedroom door open. With the closet ajar, I saw this Neil guy for the first time. He definitely wasn’t hot at all, and I’m sure his girlfriend wasn’t, either. So, I’m pretty sure he’d never had such a beautiful young girl come onto him before (unless, of course, other girls had figured out how big he was!). Rebecca was licking her lips, chatting away, and trying her best to seduce him.

Yet he didn’t just fling himself at her; he starting mumbling a little about how he’s not sure they should be hanging out in her bedroom after just meeting an hour ago. My shy friend, though, had enough self-possession to give him a coaxing smile and proclaim, “Neil, as I told you already, I’m really attracted to you, but it’s now or never! So, please quit stalling and give me a kiss.”

Well, from my vantage point, I could tell that he couldn’t resist her: he already had an enormous bulge in his corduroys. He leaned over and kissed her gently, then again, more urgently. As his lust built, his quivering hands began to play around her neck, shoulders, and then her firm breasts. Neil pulled off my friend’s short T-shirt, revealing the new satin bra that I’d helped her buy earlier in the day. French-kissing her deeply, he massaged her nipples through the bra until they were stiff.

Next, the graduate student removed the freshman’s bra and eagerly started to suck on one breast while flicking his fingers across the other. Becky’s face now had this look of concentration, and whether because he was turning her on or because she now thought that she would get her prize of a huge cum-filled condom, she began to respond. She took off his shirt and playfully grabbed at his pants.

Neil was practically drooling now over the girl’s lovely firm breasts and flat belly. But, to my surprise, he was also feeling guilty or something. He hesitated. Rebecca had to take his hand and guide it to the crotch of her jeans. This stirred him up, and he rubbed all along her fly, then her thighs and back to her crotch. My friend goaded him on by unsnapping her tight jeans and unzipping them so that this lucky guy’s eyes could feast upon the front of her brand new satin underpants, which matched her bra.

Neil gasped, started to yank down her jeans, but then paused. Becky goaded him again, “What’s up? Don’t you think that I’m at all pretty?”

Neil, that dork, stammered that she’s so incredibly pretty but that he doesn’t sleep around much and is feeling guilty. Not for long, though, once Becky pulled his hand up to her muscular stomach and convinced him to caress her soft skin. Neil then blurted out that he wanted to go slow for “another reason,” too: “I want to make sure you’re ready... I’m... a bit bigger than most guys.” No kidding, I thought to myself.

Quite honestly, I starting to get horny, too, as the scene got hotter. Neil’s big hands now were shamelessly pawing at my friend’s whole body. I watched the beautiful girl writhe around and moan in her thin satin bikini. Believe me, Neil was staring, too! As he groped her through her designer underpants, he was cooing things like, “Good girl! So pretty! So wet!”

Now, I was really turned on by the novelty of my first voyeuristic experience. But, I was petrified that if I masturbated, I’ll make noise and ruin our chances at pledging Alpha. Fortunately for Becky, she didn’t have to keep silent.

The grad student’s practiced fingers were now rubbing my friend’s clit through the bright wet satin, more and more insistently. After a little while, the eighteen-year-old just couldn’t take it anymore. She thrust her hips and ground her sex against his hand, panting and groaning, “Oh, God! Oh, Neil... It feels so good, so great! More!... A little faster!... Oh my God! I’m going to cum soon!... Cumming! I’m cumming in my panties!!”

Rebecca’s long legs and flat stomach stiffened. Next, she started to scream as Neil made her climax for at least fifteen ecstatic seconds.

Now, my friend’s vagina was soaked and relaxed and ready for action, just as Neil wanted it. As she relaxed, Neil awkwardly got undressed. Of course, my friend and I knew what was waiting: a penis of gargantuan proportions. It had immense thickness to match. Rebecca pulled out a bunch of condoms we had stowed away in her night stand: a regular, a Large, and a Magnum XL. Trying to sound casual, she inquired, “Do you want an extra-large, Neil?”

To me, her wide-eyed stare belied her inexperience. Neil must have thought she was a slut. Nevertheless, he grabbed the XL and rolled on the extra-wide condom. (You know, the big condoms are the same length as the Regulars, 8 inches, but they’re wider. By knowing that the condom was 8 inches long, I could estimate that Neil’s cock was a whopping 9 inches long.)

Neil now really took charge, thank God. He pulled Rebecca’s drenched panties to the side and slowly pushed the big head inside her pussy. She spread her legs as wide as she could, but her young vaginal canal was still very snug. I couldn’t help rubbing my own pussy a little, watching him shove his thick cock deep inside her guts.

I was impressed, and jealous, that my friend could handle so much cock. She look bewildered for a moment, but soon she was overcome with teenaged lust. She didn’t seem to mind his goofy, plain face and his pale, paunchy stomach. Impaled on his monster, Becky pushed back again and again, moaning and yelling out, “Ahhh!... Neil, you’re so huge! So deep! So deep!”

I’ve got to admit, Neil was turning out to be quite good in the sack. For instance, as his prick-tip hit Becky’s cervix, he corkscrewed his pole and rotated his hips around to bring her more pleasure.

Soon, my gorgeous friend was informing us, “Oooh, yes, I think I’m starting to cum again!” All hell broke loose as she came. She just couldn’t control her body, and in the next several minutes, Rebecca enjoyed two more powerful orgasms. Her juices spilled out of her pussy, and some of the wetness was mopped up by the panties that still encircled her waist and thigh.

I couldn’t believe how big Neil’s testicles were, or how he managed to hold off emptying them. But, finally, Neil was grunting away and his cock was glistening and red. He gave a few more deep thrusts and had an impressive orgasm through his long penis, spurting massive globs of semen into the big condom as he bellowed in relief.

Neil snuggled with the freshman for a minute, but already she was preoccupied, carefully taking the condom all the way off the cock and stowing the latex sheath under her bed for later collection. Neil was now preoccupied, too, and blubbering, “Geez, that was great, but, umm, I hope you really mean this was now and never again, because I just can’t do this again.”

Whatever!

Once the older guy snuck off, Rebecca and I recounted her tasty experience. She told me how exciting the adventure had turned out to be. I then went home, where I could masturbate in private all night long. Our prized condom was duly presented to the sisters, and my friend and I pledged Alpha and remained friends throughout college and beyond.

* * * * * * *

Now, let’s fast-forward to the weekend before Rebecca’s wedding. She’s 25 years old, still beautiful, of course, if not quite so innocent-looking. Naturally, she’s had a lot more sex by this point, but she’s about to settle down with a nice guy. I wanted her to have a last wild single night, and since I arranged her bachelorette party, I hired a hulky exotic dancer named Kevin to entertain us girls. The price of the dancer included a “tuck-in special,” where Kevin would escort the bride-to-be back to her bedroom and give her a good-night kiss.

Well, by the time the party ended, Becky and I were drunk. I told Kevin that Becky wanted her tuck-in special, and that I’d tag along as chaperone. Secretly, I was hoping to watch some sultry action as I had years before. Not that we had to pay guys to sleep with Rebecca, but Kevin and my friend couldn’t help noticing how great-looking each other was.

Very soon after the good-night kiss business, they were all over each other, not minding that I was sitting a few feet away! After Kevin was naked (which didn’t take him long: that was his profession!), he grabbed a Magnum XL condom from his wallet. Unfortunately, I hadn’t seen one of those stud-bags for seven years. Now, the condom was quickly fit onto the dancer’s enormous shaft.

Becky was stripping off her bra and panties. She was more at ease than in her freshman year of college, but she still looked surprised by Kevin’s girth. When she caught my eye, she laughed and said, “I feel guilty now, just like Big Neil did, but... it’s ‘now or never’!” With that, she lay down and braced herself for expert-quality fucking.

The rutting couple soon hit a rhythm that felt good for them, and me, too. Because this time, I was openly rubbing my pussy and groaning loudly. Before my eyes, the stranger fucked the pretty girl. Was Becky thinking of her fiancé at all, I wondered, as the gigolo pushed every wonderful inch of his tool in and out of her body? I chuckled at that one, and then chuckled again as I heard Becky indulge in her habit (as I heard 7 years ago) of announcing her orgasm: “Yesss!... Please, yes! I’m getting ready to cum!... I’m cumming!” She screamed out her pleasure and then collapsed, drunk and exhausted.

Okay, now here’s the best news. Kevin pulled out of Becky, but he was still rock-hard and huge, and excited by her beauty. I was extremely excited and unsatisfied, too, so I got into the bed. I’m not beautiful like my friend, but so what? This guy was a pro, and he wanted to cum. He smiled at me and deftly removed my party dress. With Becky snoozing on one side of the bed, Kevin’s gorgeous body was mine for the taking on the other side. He lay down on his back, grinning. I then measured Kevin’s length like I had years ago with Neil: It turned out that both dicks were about nine inches long.

Then, a bit of a difficulty presented itself. It seemed that my eyes were bigger than my genitals. The penis head was so oversized that it couldn’t get inside my tight cunt. It kept getting deflected. I wondered if I should have an initial cum, like Neil climaxing Becky in her underpants to lubricate and relax her. Fortunately, Kevin was patient and knowledgeable. He had some K-Y jelly with him, and after applying the lotion, and getting the angle right, I lowered myself slowly but surely onto the meat. It was so hot!

But besides the thickness, we also had to worry about length. I wanted the whole fucking prong in me, and I kept telling Kevin to help me push it in deeper. I don’t think we managed to get the last inch or so up my cunt, but I’d still never felt so good in my whole life.

I bounced around and up and down, feeling Kevin’s cock massage and stretch every part of my sex including the very end of the whole vagina. We fucked and fucked, and Becky didn’t even wake up until right before our simultaneous orgasms.

Being a voyeur is fun, but being fucked is even better. I still remember how great it felt to be filled up with a wide, XL nine-incher.