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.
