“I’ve never done this before.”
Jack froze in position. His cock had been at the very threshold of her opening, but at the sound of that simple sentence he leaped off of her and lay on his back, staring at the ceiling, his cock flopping and twitching.
“You’re a virgin?” he said incredulously.
“Yes, of course!” she said impatiently.
“I–I didn’t know.” The fingers that had explored her sex hadn’t gone far enough into her vagina to detect the presence or absence of a hymen.
“Well,” she said tartly, “it’s not something that comes up in everyday conversation!”
He glanced over at her. Her little joke was spoken in a shaky voice, and there was a broken little smile on her face.
“It’s been a long, long time since I’ve had a virgin,” he said reminiscently, casting his mind back to all the women he’d enjoyed over a lifetime (there were actually not all that many). “In fact, I’m not sure I’ve ever had one!”
“I’m sorry,” she said in a mixture of regret and exasperation.
“Do you want to go ahead? It’s entirely up to you.”
She looked over at him and fell into a reverie. She’d had no boyfriends in high school or college, chiefly because her timidity had led to rumors among the boys that it would be too much effort to get her into bed when so many other, more willing females were available. In one particularly disturbing episode last year, she’d had a reasonably successful date with a fellow student (just dinner at a local pizza place, followed by some idle chatting at his apartment)–but the guy had apparently felt that he’d spent enough time and money on her that she owed him some reward. He’d actually lunged at her and tried to take her clothes off; and although she was anything but a fighter, especially when a strong and determined man was concerned, she’d somehow managed to slip out of his grasp and bolt from the scene. That had traumatized her enough that she hadn’t gone out with anyone for months.
But Jack was different. She really didn’t feel their difference in age–largely because, being in her class, he struck her as (for the time being, anyway) just a student like herself. True, he had “life experience” (as that snarky professor had mentioned) that none of the other students had; but, as she spent week after week with him, she came to feel supremely comfortable in his presence. And all those dinners he had treated her to–he had made it abundantly clear that he expected nothing in return except the pleasure of her company. She was definitely not on the menu as dessert!
And so, this apparently sudden transformation of their relationship to one of physical intimacy came to seem natural and almost inevitable. Frightening as it was for her to contemplate the entry of the male organ into herself, she realized that she wanted no other man but Jack Martin to do the deed.
So she said, “Yes, I want to.”
But her seeming hesitation made Jack wonder if she was really making a sincere and heartfelt decision.
“You’re absolutely sure?” he said, looking at her keenly.
“Yes! Please . . . go into me.”
Your wish is my command, my dear, his expression told her. Then another thought occurred to him.
“Do you want to be on top? It might be easier for you.”
“No,” she snapped back, sounding irritated. “You be on top.”
So he climbed back on top of her. But as he looked down at her slight but tempting form, he almost thought she looked like a sort of sacrificial lamb. And maybe she was!
At first, as he brought his cock to her crevice, he just rubbed it up and down between her labia, coating it with her own juices. She seemed to like that–but when he entered an inch or so, she suddenly let out a pathetic little whimper, and her face crumpled in a grimace. He found it hard to imagine she was feeling pain right then: probably she was just anticipating the pain she would feel in the very next moment. And that wrung his heart.
His cock then encountered that absurd barrier in her vagina. He knew there was no easy way to do this, so he just forged on ahead, his cock acting like a battering ram breaking through the gateway of some medieval castle.
Now she did cry out in obvious pain–but, as he lowered himself onto her body, she clung frantically to him as if that might help her get through the experience. She unconsciously wrapped her legs around his hips; this made it easier for him to go in, and it seemed to lessen her agony a bit. But she was still in extreme discomfort, and a big tear was squeezed out of each eye. He tried to distract her by kissing her all over her face and neck and by stroking her back and shoulders and those sweet little breasts, along with her small but firm bottom. At one point he slid his hand between their bodies and placed his fingers on either side of his cock, as if to convince himself that he was actually in her.
He was now certain this was the first virgin he’d ever had.
And so it wasn’t surprising that, in addition to the many weeks during which Jack had “courted” Vanessa in a very old-fashioned manner, the exquisite warmth, wetness, and tightness of her vagina caused him to explode in her a lot sooner than he expected. His orgasm was accompanied by heavy grunts that went right into her ears, as his head was positioned next to her face; and as she felt for the first time the depositing of seed into her cavity, her heart was lifted by a sense of the magnitude and significance of the event. His discharge never seemed to end; and when it finally did so, he collapsed on top of her like a dead weight.
For a while she liked the feel of his body on her own, and she kept her arms wrapped closely around his shoulders for minutes. But then she signaled that she’d like him to get off–and out–of her, and he grudgingly complied.
His copious emission almost immediately began leaking out of her, creating the proverbial “wet spot” between her legs. And yet, she couldn’t quite believe that the whole thing had really happened, and she tentatively placed a few fingers in the area to make sure. Yes, his come was definitely there!
When she held her fingers up to her face, she realized that there were little streaks of red mingled with the white viscosity of his emission. Suddenly alarmed and embarrassed, she leaped out of bed and rushed to the bathroom, where she cleaned up the mess. Jack, for his part, used some Kleenex to wipe the small amount of blood on his member.
Returning to the bedroom, she flung herself onto his supine body, covering him just as he had covered her a few minutes before. Of course, her own body was diminutive compared with his, and she had to drive out the thought that she was a daughter cuddling up with a beloved father. His actions, though, were not that of a father: he kissed her passionately all over her face and neck, rubbed her back and bottom, and generally conveyed the impression that he wanted her close to him always.
And the inevitable happened: he got hard again.
The process was aided by Vanessa’s occasional reaching down and stroking that organ. She was still mesmerized by the strange things it was capable of doing, and so she couldn’t help touching and fondling it, as if it were her favorite new toy. But when it actually did engorge again, she felt a little flutter of alarm.
“You . . . want to do it again?” she asked.
The worry in her voice troubled him. “Only if you do, dear.”
“I–I’m a little sore down there. You know, first time and all. Is there something else we can do?”
That was a loaded question, although Vanessa didn’t seem aware of it. All manner of things–from a handjob to a blowjob to something even more daring–flitted through his mind. Before he fully realized what he was saying, he replied: “Well, I could go into your bottom.”
The moment the words were out, Jack internally kicked himself for being a scumbag. The blood drained entirely out of Vanessa’s face as she pictured in her mind the obscenity of the act. She had actually had a conversation on this very subject about a year ago when a friend who, one morning, had met her on campus and blurted out, “Do you know what my boyfriend did to me? He went into my ass!” Vanessa was only dimly aware of this procedure and said incredulously, “Does it fit there?” “Oh, yeah, it fits–barely,” the friend had said. “‘Course, you gotta use lube. Even so, it hurts like hell. Talk about a literal pain in the butt! And yet, I kinda liked it–you feel real close to your guy when you do it . . .”