What If? Ch. 01

Leila and I had been shopping and generally hanging out for most of the day. The Spring Carnival celebration at the university I attended was only a few weeks away, and all the fraternal organizations were in high gear preparing for it. Spring Carnival was a pretty big deal on campus; consisting of a number of "friendly" competitions between the various fraternal organizations. One of these competitions was the "booth," where each participating organization built a midway game that fit within the overall theme of the carnival. My frat went pretty much all out for most events and for this one in particular—trying our best to win each year—and this year was no different. I was currently working on the finishing touches to our booth, and I'd spent the day shopping with Leila for those little accessories and details that make the difference between a half-hearted effort and a polished, winning one.

Leila was a little sister at our frat and a good friend of mine. She was a student at the state university which was literally next door to the private school I attended. She had drifted up to one of our fraternity parties and become interested in one of the brothers (whom she eventually began dating). While dating him, she made a number of other friends among the bothers and little sisters, and even though she and he ran a continually hot and cold relationship, she decided to continue her involvement with us by becoming a little sister.

While I had no idea what Leila thought of me (other than considering me a good friend), I knew very well what I thought of her (apart from considering her a good friend as well). I found her incredibly exotic and attractive. She was about 5 and a half feet tall and very vivacious. She had shoulder length brown hair, green eyes that just lit up when she laughed, and a very light olive complexion (her background had a bit of Middle-Eastern blood in it). Some of the brothers had described her as stocky (she'd probably be classed as a BBW in today's parlance, but only barely), but those were the ones who tended to be interested in the Barbie-like blondes on campus. I thought Leila was gorgeous with the largest and most magnificent breasts that I ever fanaticized about seeing.

While Spring Carnival may have been only a few weeks away, Spring felt like it was a great deal further off. The day had dawned grey and cold with the only change by mid afternoon being the addition of an occasional spattering of rain. But we had dressed for the day, me in a ski sweater and light jacket and Leila in a tight sweater (any sweater stretched over those breasts was tight!) and a winter coat. We'd been comfortable during the day, but with the sun going down and the drizzle picking up, we were starting to feel the chill. It was time to call it a day.

It was about dinner time, and we were riding the bus back to the stop closest to her dorm. I had planned on walking her back to her dorm room, and after that, I'd hike the additional mile and half up to my frat. With the weekend, and no meal service at the frat, we were discussing alternatives to stop and grab a bite. In the interest of economy (hey, we were both starving students), we settled on a sandwich shop near to both her dorm and the bus stop. We chatted at the counter as we waited for our food.

"So, what are you doing for the rest of the evening?" Leila asked.

I stared out the window for a few minutes, mentally going through my to-do list. "I'm not sure. I've got some work due next week in my Stats class, but I've got most of it done already. I've also got some reading to do, but frankly I'm not in the mood. I'll probably be working on the booth until I decide to crash."

She giggled. "Your life is one long string of events on the edge, isn't it? Nothing but Spring Carnival and classes."

"Yeah. At least until Carnival's over. After that, I'm planning on sleeping for a week or so."

"Why don't you come on up to my dorm and we'll eat dinner there? Take a break from booth for at least the rest of the evening. Your classes aren't in danger. And God knows, it's better seating than here. Besides, that'll prevent me from walking these unsafe streets at night," she said as she winked at me.

"You're right," I said. "It is better than sitting here. Let's go." We grabbed our sandwiches and headed for her dorm.

Her dorm was about ...

As she was pushing the door to her dorm room open, she looked back over her shoulder. "I apologize for the mess. I don't have a room mate, so it encourages me to be a bit of a slob."

"You call this being a slob?" as I stepped into her room. "You've seen my room; it needs an archaeologist more than a housekeeper!" Her room was neat and tidy and surprisingly large. "I haven't been in these dorms before; your room is larger than I imagined."

"It's nice to have the space to spread out, but I could do with a bit less space. These were originally intended for two students, but when they remodeled a few years ago, they changed them to singles," she commented. "Just drop your stuff anywhere and get comfortable."

We sat down cross-legged on the floor, and dug into our dinner. As we ate, we continued to idly chat about classes, the upcoming Spring Carnival, brothers at the house, our respective families, and general interests. Leila was fun to be around; she had an infectious laugh and was constantly bright and bubbly. This evening was no different, and before we knew it, it was going on 9 PM. In fact she was the one who noticed when she glanced at her alarm clock above her bed.

"Geez! It's nearly nine!" she cried.

"So? What happens at nine?"

"It's not what happens at nine; it's what happened at eight! They closed the dorm doors to anyone but students at eight. If we try to sneak you out now, you're going to be in a ton of trouble."

"Ah, man; that's all I need!" I sighed. "Now what? Is there a back stairwell or something?"

"Nope. You really are stuck here." She thought for a minute. "Look it's not a problem to me if you stay tonight, the other girls on this floor have guys stay all the time. I mean; I don't mind if you don't mind."

"Are you sure? I can sleep comfortably on the floor as long as it's ok with you."

"Well, we'll work that out later. For now, it's settled. We'll sign you out in the morning."

And with that, we settled back down next to each other and continued chatting. Our thighs were touching as we sat next to each other, and I periodically had some definitely non-sibling-like thoughts about my fraternal little sister. I was exceptionally grateful that I had a pair of tight jeans on. While the bulge in my crotch might be noticeable, it couldn't get too extreme. We had been talking relatively comfortably (with the exception of my imprisoned erection) for about an hour when the conversation reached one of those inevitable lulls that occasionally happen. Leila looked at me with a funny expression for a moment before talking.

"Do you mind if I tell you something?"

"Of course not. What is it?"

"Well, I feel a little uncomfortable saying this, but you're one of my best friends, and you always make me feel at ease...I've always admired your body." She rushed on to say: "I mean, you have a really nice build, and I think you're very attractive. I really like your wide shoulders and your little butt...I'm sorry; I probably shouldn't have said anything."

To say I was mildly surprised would have been like saying Einstein was a bit brighter than average. This was the last thing I was expecting to hear. I mean, I had a decent build at the time (about 6 feet tall and about 165 pounds with somewhat broad shoulders and narrow waist and hips), but I honestly thought she'd never noticed me. Given the reaction of my dick off and on for the last hour though, my libido got the better of me in my answer. Rather than politely acknowledging her compliment, I said what was really on my mind: "I'm glad you did. I'm very flattered to hear that...Do you mind if I tell you something?"

"Not given what I've just told you."

"I admire your body as well. I find you...extremely... attractive..." And here's where my loins took over the talking from my brain "...and you have the most magnificent breasts of anyone I know."

She blushed, looked down, and giggled. "Magnificent, huh? ... You really think so?"

"Absolutely." It was quiet again for a few moments before she spoke.

"Well, I'm going to get dressed for bed. I'll just change in the bathroom."

That left me with my thoughts in her room. I kept running the conversation through my mind, thinking that I'd just set a new record in conversational stupidity, even by my standards. My comments had obviously put her off, and I'd overstepped my bounds. I sighed. It promised to be a long, chilly night in every sense of those words.

A few moments later the bathroom latch clicked in the silence as she opened the door. She walked out of the bathroom, clad only in a long, sheer, cotton nightgown and panties. She looked terrific; her large, firm breasts threatening to break free from their flimsy prison. She stood there looking down, as if thinking, before she spoke.

"Do you want to see them?" she asked quietly.

"See what?" I dumbly responded.

"My breasts."

Again, I answered without thinking. "There's nothing I'd like more."

As she began to slip her nightgown off her shoulders, time seemed to slow down. 'Oh my God,' I thought to myself as the sleeves slipped over her shoulders and fell to the floor. Her breasts were as beautiful as I imagined them; enormous and defying gravity with aureoles at least two and a half inches across and nipples at least a half inch long. I realized that I'd stopped breathing and gasped in a huge breath. I let it out as I stood up and said "would you like to see my body as well?"

She hesitated for a second and said: "I would."

I reached down to my waist and pulled my sweater over my head. Tossing it on the bed, I began to pull my t-shirt over my head as well. While it was clearing my head and covering my eyes, Leila apparently made a decision. Hooking her thumbs in the side of her panties she had them to her knees by the time I looked up from tossing my t-shirt on top of my sweater. I suddenly couldn't breathe at all. Her pussy was gorgeous; a lovely mound of trimmed brown pubic hair above her swollen, wet lips. My dick immediately went to full alert while she gave me an apprehensive look, as if unsure that she'd just made the right decision. 'Here goes nothing,' I thought. Looking directly in her eyes, I unbuckled my belt and stepped out of my jeans. Her look of apprehension was replaced with keen interest as she saw the bulge in my underwear. I hooked my thumbs in the waistband and stepped out of them as well; my rigid prick springing upwards to slap my stomach. She took a step closer, eyeing my cock.

"May I touch it?"

Again, I said: "There's nothing I'd like more." She reached down and gently caressed my throbbing dick as it jumped at her touch. She slowly stroked it along its length, and if anything, it got harder. Her eyes returned to mine. "Would you like to touch them?" she asked. I answered by cupping her heavy breasts. They were firm and full, and her large nipples quickly hardened under my touch. I felt my dick harden to the point of pain as I leaned over to kiss them. Her quick intake of breath told me that my intuition was correct; her breasts were extremely sensitive. I took one of her nipples in my mouth and sucked firmly on it, running my tongue around it as I sucked. I heard a low rumble in her throat as she squeezed by rock-hard cock.

She leaned down to put her mouth next to my ear. "I want to taste you," she whispered.

What a coincidence; I wanted her to do that too. I raised up as she sank to her knees and took my erection in her warm, wet mouth. My knees nearly buckled at the sensation of her lips on the head of my cock. She sat there, with just the head in her mouth gently licking the underside of it while she moaned to herself. I reached down and ran my fingers through her hair, pausing as my hands reached the back of her head to slowly pull her mouth further onto my dick. I began to slowly move my hips back and forth, gently fucking her mouth. Her moaning got louder as she reached around my hips, clutching the cheeks of my ass and pulling me closer to her and my dick further into her mouth. I wasn't going to last long like this, and tilted her head back slightly to look at her.

"I'm going to cum," I managed to grunt out. She took her mouth from around my cock, smiled, and went back to sucking me. With my hands behind her head and my fingers running through her hair, I returned to gently fucking her mouth. I soon began to feel that familiar sensation at the base of my prick. "Oh, man...I'm cumming!" And with that I shot a load into her waiting mouth. Without pausing, she moaned and swallowed, and I shot twice more. She continued sucking for a few minutes as I shuddered from the intense feelings of her mouth on the swollen head my cock following my orgasm. I reached my hands down next to her breasts and slowly drew her up standing. "I'd like to return the favor."

She got a hesitant look on her face for a moment and said, "I've never tried that. But I want you to know that I have trouble cumming. In fact, I've never had an orgasm before."

"Never!?"

"Never."

"Well, I'd at least like to try." I gently pushed her down onto her bed, where she sat with her legs pressed together. I reached between her knees and gently pulled them apart. She tensed as I slid my hands up her thighs to either side of her bare cunt. It was wet and glistening; while she was nervous, she was also horny as hell. I looked up at her and told her it was ok if she didn't want to go any further. She took a deep breath, and as she let it out, she nodded her head. I leaned forward and gently touched her clit with my tongue. She leaned forward as she shuddered and moaned. I sat up and gently massaged her breasts. "Just relax. You're too tense right now. Don't worry; I won't do anything you don't want me to."

With that, she slowly leaned back on her elbows and spread her legs a bit further. "Go ahead. I'll try to relax," she said. "It's just that...well...no one has ever done that before."

"You've never had anyone eat this gorgeous pussy before?"

She smiled and blushed at my use of the word 'pussy.'

"Never."

I slowly lowered my tongue back to her pussy; running it slowly up and down just between her lips. I heard her groan and settle further back onto her bed. I went to work in earnest, tongue-fucking her pussy and nibbling on her clit. She began to breathe more heavily and slowly moved her hips up towards my face. I reached one hand under her ass while I slid my other hand up to begin rubbing her tits again. As my hand began rubbing her ass, her moaning got a bit louder again. I slowly drew my hand along the crack of her ass, pausing to gently brush the rosebud of her asshole and continuing up to slowly insert a finger in her dripping pussy. She arched her back and began fucking my tongue and finger with a vengeance. I pulled my finger out for a second to taste it, causing her to moan in disappointment. I licked my index and middle fingers and slowly inserted them back in her cunt, leaning forward to suck her clit into my mouth. As soon as I did that; both her hands clutched the back of my head as she ground her hips into my face. A second later, she shuddered violently as she yelled: "Oh God, don't stop...oh God, oh GOD, OH GOD, OOOHHH GGGOOODDD!".

She shuddered for a few minutes and then looked weakly down at me. "Oh my God, that felt good. I've never had that happen before."

"Don't you masturbate?"

She blushed and glanced away. "No, I don't. I've always been taught that sex is dirty and that masturbation is something that people just don't do."

I smiled at her and gently brushed my fingers across her clit causing a quick spasm with another orgasm. I raised up on my knees to show her my erect cock. "Would you like to cum again? Only this time while trying a little something different?"

Her eyes glazed over as she looked at my prick. "Mmm. I'd love to put that cock in my waiting pussy! What have you got in mind?"

"Sit up on the edge of the bed, and spread your legs for me." She gave me a wicked look and quickly scrambled into position on the edge of the bed.

"Is this what you had in mind?" she asked as leaned back on her left elbow and slowly ran the finger of her right hand along her slit.

"Perfect." I moved between her legs and slowly bent forward to suck on the nipple of her right breast. Her quick intake of breath told me that she was still enjoying herself. Keeping her nipple in my mouth, I inched my hips forward until the head of my cock just grazed against the lips of her pussy. In that position, I began slowly sliding it up and down the length of her wet and dripping gash. She moaned deeply and reached down to raise my head up from her breasts. Looking directly at me, she whispered intensely "Oh, God, I want you to fuck me!"

Her pussy was so wet that I didn't need any other lubrication. I adjusted the angle of my hips slightly until the head of my dick was just starting to part the lips of her cunt. I paused there and looked into Leila's eyes.

"Are you sure you want to do this?"

"I've never been more sure. Please stop teasing me and just fuck me!"

Taking a deep breath, I slowly pushed myself into her slick entrance. As I did, she moaned deeply. When our hips met, she reached up suddenly and grabbed my ass, holding me in place.

"Stop! Stop. I just want to feel this for a second." She purred "You feel so good in there!" She slowly started to move my hips with her hands; in and out; basically fucking herself with my hips. I gradually began moving my hips with her hands, increasing the speed and intensity of our thrusting into each other. "Unh. Unh. Unh." Each thrust brought another grunt from her as she began thrusting into me. After a few moments, I leaned back and put my full weight on my knees while continuing to thrust into her hips.

"What are you doing?" Leila asked.

"I'm watching us fuck."

She giggled and asked: "And how's it look?"

"Fabulous. Your cunt is beautiful; just watching it get fucked is nearly enough to make me cum. Being the one fucking it is just indescribable!"

"Are you close to cumming?"

"I am. But I'd like you to cum with me." Taking her right hand, I placed her fingertips on her clit. "Rub yourself. I want you to masturbate while I fuck you." She gave me a wicked grin and began slowly circling her clit with her index finger. As she ran her finger around her clit, her head slowly fell backwards and moaned deeply again.

After a few minutes of this, her breathing began noticeably quickening. For a girl that had never had an orgasm before, she seemed to be making up for lost time. I silently said a prayer of thanks as I'd been thinking of anything I could—booth, my homework, the balance in my checking account—to take my mind off my impending release so that could cum together. As the pace of her hand quickened, I pulled out all the stops and began fucking her in earnest. In just a few moments, Leila began a shuddering climax, reaching her hands around to grab both cheeks of my ass. As she did so, I felt that familiar rise in my balls. I squeezed my eyes shut and began pumping a hot, sticky load deep into her waiting box.

"Oh, yes! That's it! Fuck my cunt! Cum in my cunt!"

With a final shove, I collapsed on Leila, my head resting between her enormous tits; both of us gasping for breath. We lay like that for another few minutes, catching our breath, before I slowly raised back up and gently kissed each of her nipples, causing her to shudder briefly. Leila raised back up on her elbows and looked down at me.