First Three Times

Tracy and Alec had become friends in the fall of 1988, at the very beginning of their freshman year. They had been partnered for an assignment in a class, and they found quickly that they got along well. Similar sense of humor, many overlapping interests.

Their talks outside of class were serious and deep, and they found they trusted each other. They each talked about old high school relationships, family problems, and other topics that were ordinarily difficult to get into with just anyone.

They soon realized they were attracted to one another. They made out a few times, but it hadn't really led anywhere. The furthest they'd gone was Alec taking Tracy's shirt off and sucking on her small high breasts. Another time, she had briefly felt for his erection through his pants, but they were interrupted before anything else could happen. Then they'd each been overwhelmed by classes and fall semester finals, and the timing just never seemed right again.

They nevertheless remained friends. Alec, despite finding her very sexy, had not been hurt that they'd failed to hook up. He had moved on, sleeping with three or four other girls over the winter and early spring. For the last few months, though, he'd been focussing again on his classes.

Tonight, they were in his dorm room, talking on the broad old couch beneath his roommate's loft bed. Alec's roommate, Scott, was studying with some friends across campus, and had been out all evening.

Alec told her about his brief winter flings, and she asked for lots of details.

He'd had very straightforward sex with one girl several times over a month. He'd gotten enthusiastic but inexpert blowjobs from another girl after eating her pussy in the backseat of her car, several weekends in a row on deserted suburban side streets. And he had a single long night of vigorous fucking with another girl, in lots of positions and in every room (including the garage) of her parents' house while they were away; it was the first time he'd ever fucked someone in the ass.

At last, they turned to Tracy's love life.

"I have a big problem," Tracy said. "Well," she added, "two big problems, actually... And I've wanted to talk to you about it."

Tracy told him that when she had been home over the holidays, she'd reconnected with Dean, a boyfriend from high school, and it was getting serious. They had been dating all winter and spring. Now, in early May, Dean was very eager to have sex, but she was still a virgin.

She really wanted to have sex, too, but she was nervous. Back in high school, she had never gone very far with Dean. But now, they'd been fooling around a lot more, and it had become much more intense. They'd finally gotten naked, and they were having lots of oral sex and mutual masturbation. But Dean was...

She paused.

"He's really huge," she said.

"How huge?"

"Well, I've... How do I put this? When I jerk him off, my middle finger and thumb just barely touch." She circled her wrist with her hand to demonstrate.

Alec raised his eyebrows. "Oh. Wow. That's..." He felt his cock begin to stiffen.

"Yeah," Tracy agreed with a sigh. "And I've given him head a few times, too, but my mouth almost isn't wide enough."

When Tracy knocked, he was naked, having just gotten back from a shower. So he just pulled on a tee shirt and heavy, baggy sweatpants with no underwear. It was just Tracy. No big deal. It suddenly felt, in retrospect, like a very poor wardrobe choice.

Telling her about all his own sex adventures hadn't aroused him at all. But now he was suddenly very aware of his cock, loose in his sweats, getting harder.

"Yes," he said slowly, "he must be enormous. So, your problem...?"

"Well, as you know, I've never had sex before, so that's a source of nervousness — but I'm really scared he won't fit, or at the very least it will hurt like hell. My roommate suggested I find a dildo or something, but I have no idea how to do that!" Their college was on the edge of a small town, an hour from the nearest city. And Tracy wasn't exactly keen on visiting a sex shop anyway.

"I tried using my fingers to, you know, to stretch myself out a little, but..." She dropped her gaze. She had dirty blonde hair, and very wide cheekbones. Her almond-shaped eyes were light brown. She was a big girl, exactly Alec's height. Broad ass and long legs. Her breasts were small and gumdrop-shaped, with up-turned nipples. She rarely wore a bra, certainly not now that the weather had gotten so nice. His sex stories had gotten her nipples to harden, and they were perked up again now.

"Well, do any of your friends have a dildo you could borrow?" he asked. This was an odd conversation they were having all of a sudden. He wasn't sure if he'd ever said the word "dildo" out loud before.

"I... No. I don't think so. I haven't asked anyone. It's one thing to talk with someone — you, for instance, or my roommate — but to interview people about their sex toys? Um, I don't know."

"Fair point." There was a pause. "Well, I don't have a dildo either, if you were wondering."

"No," she laughed. "No, but..." She looked at Alec, and then her eyes dropped to his crotch. "You have something else."

Alec looked at her blankly for a second, then laughed. "Oh god! Um, yes, I guess I do. But... what are you suggesting?"

"Well, no offense, but you're probably smaller than my boyfriend, and I like you, and I trust you, and..." She was still staring at his crotch.

"Wait. You want me to... to go first?" His cock was getting harder and harder.

"Well, can I see it first?" She hadn't stopped looking at his erection, growing more obvious with each heartbeat.

He considered for a second, then stood up and eased his sweats down. The elastic held them mid-thigh. "I'm not completely, um, hard yet. But, well. This is basically it."

"Oh..." She reached out hesitantly, drew back, then reached out again and took it in her hand.

"Okay," he managed to say through grit teeth, "that will definitely get me harder."

"Funny, Dean isn't actually much longer than you. He's just really thick." She stroked him several times, and he couldn't help but notice that her thumb overlapped to the first knuckle of her middle finger. He was fully erect now and he felt rather close to coming. It had been a dry spring for him.

"Careful," he warned. "I'm kind of close."

"Oh, sorry!" She pulled her hand away completely, and sat back, studying his penis, curving up slightly, and with the faintest bend to the left. "And I'm sorry we never got this far before. It's actually quite lovely. Can I say that?"

She leaned forward and impulsively pulled her tee shirt off, revealing her bare breasts.

Just then, the door flew open and Scott rushed in. "Hey, I totally forgot my notes for — Whoa, holy shit! Jeez, I'm so sorry!..."

He shielded his eyes but then peeked out at Tracy, who had crossed her arms over her breasts. Scott was confused. "Hey, Tracy? I'm sorry, I didn't know you guys were back together..."

Scott had harbored a secret crush on Tracy ever since meeting her. Alec having her over all the time had been exquisite torture. Tracy and Alec had made out on the couch once late at night, while he was in bed above them. They'd thought he was asleep, and this had been the night Alec had managed to get Tracy out of her shirt. Scott had peeked over and watched as Alec suckled and caressed those gorgeous tits, wishing it was him down there instead.

Alec had tugged his sweats back up. And his erection, of course, was gone in a second.

Scott was a big guy, broad-shouldered, heavy-limbed, and at 6'3", he was nearly six inches taller than Alec and Tracy. Childhood on a farm, football in high school. He'd only been with one other girl before, the summer before college, and they'd only slept together three times.

"No, Alec and I aren't together anymore," Tracy began. "We were just talking. I'm dating Dean now, and I've never had sex, and—"

"She's worried Dean's dick is too big," Alec blurted, "so—"

Scott was stunned. "So, what? Were you measuring Alec? Why?"

Tracy tried covering her eyes, which exposed one of her breasts. Scott noticed, but Tracy didn't. "I was just seeing if they're all that big, and..." She looked up at Scott, then down at his crotch. "And this evening can't get any more weird or awkward, so... Can I see yours?"

Tracy dropped her arm, baring her breasts to him.

"I can step out, give you some privacy," Alec finally said, gallantly.

But Scott, as if in a dream, had already unbuckled his pants and was pulling them down. His eyes were locked on Tracy's tits. His cock jumped up and was erect in no time.

Alec stared. He'd never seen another guy's erection before. The first thing he noticed, however, was that despite being a big guy, Scott's cock was noticeably smaller than Alec's. Thinner, and probably as much as a half-inch shorter. And it was obvious that it was fully, even painfully, erect. This was apparently as big as it could get.

"It's so pretty!" Tracy sighed. "Oh, sorry! I keep using the wrong word to describe your things. It's not pretty — it's hot, it's gorgeous. It's just... God, I love erect penises."

She paused.

"Okay guys, I have a crazy idea. Scott, will you... will you make love to me? I'm a virgin but I'm on the pill, so it'll be okay if you, y'know..."

"Oh wow, I don't know," Scott said. His straining erection, however, was absolutely sure.

"Please," she said. "It would mean so much to me. I think my, um, my vulva is too small, and I don't know if I can have sex... Please help."

There was a long pause. Alec had long suspected that Scott was deeply attracted to Tracy, and guessed that he desperately wanted to have sex with her. "I'll give you some privacy," Alec said, deciding to act as if Scott had already agreed.

"No. Please stay," Tracy begged. "I want you with me. Anyway," she added with a wild grin, "you're next." She turned back to Scott. "Do you mind if Alec stays?"

"I... No," Scott said slowly, "I guess that's... fine?"

"I won't watch or anything. I'll just climb up into my bed, and... you know, wait." Alec went to the door, and locked it.

When he turned back, Tracy had stepped out of her skirt and was now wearing only thin white panties. She walked to Scott and began undressing him. His pants and boxers were already around his ankles. She pulled his shirt up and over, then knelt down to help him step out of his pants and shoes. Her face was right at his cock and she took a second to gaze at it. Precum was practically pouring out of him, he was so excited.

She took Scott's hand and drew him to the couch. "Lie down on your back," she told him, as she peeled off her panties. She climbed over him. He reached up and cupped her breasts, then kneaded at them heavily. "Easy," she said. "Sorry," he replied.

She arranged herself in a squat over his straining cock. "Can you maybe use your fingers to part my lips a little? Then I'll guide you in."

He fumbled at her pussy, one hand on each side, and delicately parted her labia. She reached down and steadied his cock. Slowly she eased down, and his cock slid up and into her.

"Oh, oh my god..." she sighed. She let herself drop very slowly, excruciatingly slowly. "I'm so tight, oh, it kind of hurts..."

"I can stop—" Scott said.

"No no: it's good. It's... Oh..." And she gradually began sliding up and down on his cock. After a minute, she settled down onto him, and held still. Then she climbed off. "Can you be on top now?"

Scott leapt up. She lay down and he eagerly mounted her.

"I'm opening up a little, so please do whatever you want," she said.

Scott obliged by pounding at her frantically. After only a minute or two, he asked, "I can...?"

"Yes, yes!"

Without breaking his pace, he suddenly groaned. He didn't stop slamming her until he'd finished coming. He said, "Oh, oh, oh," quietly, on each impact. Then he ground himself into her and held still.

All this time, Alec had watched. At first, he just stood and stared, with every intention of climbing into his bed and giving them at least a little privacy, but he was hypnotized. And it didn't matter. Neither Tracy nor Scott were paying him the slightest attention. It really was as if he wasn't there. He moved over to his desk and sat on this desk chair. He was hard again. He had taken off his tee shirt when Tracy had climbed onto Scott, and then, a few minutes later, he pulled his sweats off as well. He sat naked at his desk, slowly stroking himself.

When Scott had finished, Tracy held him for a moment than gently rolled him off. His cock, softening, flopped against him. He stood up. Alec suddenly realized he'd just watched Tracy lose her virginity.

"Alec, please..." she said, gesturing him to her. He practically jumped up. His erection was almost painfully full and the tip was damp with precum.

Scott couldn't help but look at Alec's dick. He breathed, impressed. "Wow, you're actually bigger than I am. Surprising..."

Alec nodded in humble acknowledgement of the compliment, and approached Tracy.

"Top or bottom?" he asked.

"Oh, on top. I love feeling the weight of a man..."

Because Alec was thicker than Scott, she was a very tight fit for him, even after her first time. He mounted her and slowly eased his cock into her. Her own wetness, and Scott's semen, allowed him to slide in a little more easily than it would have been otherwise. After getting all the way in, he held still for a moment to let her get used to it. Then he started to pull out and thrust in again, slowly, steadily.

Of course, he had already been close to coming when she'd touched him before, and now he was actually having sex for the first time in probably four months. Not to mention he'd just watched Tracy having sex with another guy only a moment before, so he was very aroused and extremely close.

"I won't last much longer," he said.

"That's okay. You've already done enough. You both have." She looked over at Scott, who was still naked, and already getting hard again.

"Okay then, how about a little action?" and Alec began fucking her hard, slamming against her in heavy, violent thrusts. After only a few of these, he started to come. He stopped suddenly on one of his thrusts and pushed himself against her, grinding his pubic bone against her clit.

Feeling him pulse inside her, feeling the jets of cum — and all of this for the second time in under ten minutes — she suddenly spasmed into a massive orgasm of her own, her first that evening. Crying out, she clawed at his ass and back, and held him against her.

Meanwhile, Scott had been jerking off, watching this. Tracy looked over at him again after opening her eyes. "Yes yes yes," she sighed, and eased Alec away. He climbed up and made room for Scott, who rolled her over. She got up on all fours, and Scott slid quickly and wetly into her from behind. He grabbed her hips and moved in and out slowly.

Having just come moments before, he knew he'd last much longer this time. He decided to make this one count. He'd lusted for her all year and now she had just lost her virginity to him. This was unbelievable. He ran his hands up and down her spine, and cupped her ass and hips. He went slow, then very fast, then slow again. He felt her shudder through another orgasm. He was giddy that he had made her come as well. He fell into a rhythm, fucking her with a steady pace.

Alec watched for a while, and after about ten minutes, he found himself getting hard again, too. He sat down at Scott's desk, where Tracy would be looking right at him, and stroked his cock leisurely. Once he was completely hard, she looked up and said, "Come here..."

Alec sat down in front of her at the head of the couch. She engulfed his cock in her mouth and started sucking hard. He could feel Scott's movements by how deeply she took him into her throat.

The three of them stayed in this arrangement for twenty more minutes, when finally Scott started making sounds that suggested he was finally close to his second climax.

"Harder," she said to him thickly, without bothering to take Alec's cock out of her mouth. Scott picked up his pace and started slamming into her. So hard, in fact, that she was having trouble sucking on Alec. Her teeth clamped down once and Alec yelped.

"Sorry," Scott and Tracy said together. Tracy stopped sucking. Scott pounded harder, then grunted as he started to come. This time he held still to really feel himself throb inside her. She soon climaxed again, her cunt clutching at Scott's cock.

As she felt Scott finish his orgasm, she renewed her attention to Alec, and sucked on him frantically. Scott pulled out slowly, and sat back, exhausted. Tracy dropped from her all-fours position, and curled up to focus all her attention on Alec's cock. She stroked his shaft with one hand, cupped his balls with the other, and bobbed her head in time with the movements of her hands. When he finally started coming in her mouth, she gulped noisily, swallowing him down.

The three of them were drained. The two boys suddenly found themselves very self-conscious. Tracy rolled over and stretched luxuriously. She entangled her feet around Scott, and reached her arms up to hug Alec.

"So delicious, this was amazing... Thank you!" she sighed, and she spontaneously shuddered with a surprised gasp into a third, quieter orgasm.

The two boys sat back and gazed at the girl curled up between them.

Then the room-phone rang. They all jumped. Alec got up and answered the phone. "Hello? Yes. Yeah, she's here. Oh, shit — really? Okay. Um, okay."

The other two watched him anxiously. Scott reached over and untangled his boxers from the clump of clothing on the floor. Tracy stayed naked, and actually stretched out. She pulled some kleenex from the nearby box and was absently wiping the masses of cum from her thigh as it dribbled from her pussy.

Alec hung up. "Um, that was Wendy, your roommate," he said to Tracy, pulling his sweatpants on. "Dean just arrived. He wants to see you and wanted to know where you were."

"Shit!" She jumped up suddenly, grabbing another handful of kleenex and wadding them up between her legs. "Did she tell him I was over here? Is he coming?"

"No no! She said you were studying with some friends, and that she'd see if you could get away. She said he's antsy but willing to wait there till you get back."

Then it hit both boys, at the same time. All this had been to help her have sex with someone else. She was going to go back to her boyfriend now and sleep with him. And be with him. And stay with him. Their eyes met briefly, then they looked away.

Scott had always struck Alec as rather naive, or at least without guile. Scott looked at Tracy as she was frantically mopping up her crotch, and he asked the question Alec wanted to ask. "Are you really going to him?"

She stopped, still bent over, with wads of cum-drenched tissues in her fist, and looked at him. "Oh honey..." she sighed. "I don't know what the hell I'm going to do."

Tracy got herself cleaned up as best she could, dressed, then went down to the women's bathroom on the floor below to wash up a little more thoroughly.

While she was gone, Scott and Alec looked at each other. "Well," Alec said finally, to break the ice, "it's a good thing you and I get along, otherwise this could have been kind of awkward."

Scott tried to laugh, but he was clearly shaken. "This was incredible, but you know I've had a huge crush on Tracy—"

"I know. But whatever happens, think of this: you were her first. And seriously, I'm happy to back off a bit. She and I are friends, and I'm really not interested in a relationship with her. (Unless it meant that he wasn't going to stay with Dean...) So, I can give you space so you can spend more time with her. No matter whether she stays with Dean or not. I know she likes you — obviously! — but you should take time to get to know her better, and let her get to know you better, too. You always sort of faded away whenever she was over here, even when we were just studying together or watching movies."