In the following weeks, Tom and Victoria familiarized quickly with each other’s body, discovering erogenous zone and personal pleasure triggers, making their enjoyment of sex better and better. Still, an obstacle remained on their way to ultimate satisfaction. Victoria was a virgin and she meant to remain one until she got married. As much as she liked Tom and loved him and had fun with him, she told him in no uncertain terms that she was not going to let him fuck her. He could rub and finger and lick her pussy to his heart’s content, but his cock was not allowed in there. Never.
Tom had accepted Victoria’s rule when she set it. He was a bit surprised that a smart independent girl like her would cling to what he thought was an obsolete standard of female virtue. His family was quite open-minded and easygoing as far as traditional morals and social norms were concerned, but Victoria’s religious background had shaped her otherwise, at least in this one specific regard.
At first the ban on intercourse was no problem. Both teens got all the satisfaction they needed through long and lustful oral marathons that left their bodies sated and their mouths glistening with one another’s juices. But after a while, despite the insane pleasure that Victoria’s soft lips and warm mouth gave him when they were wrapped tightly around his big cock, Tom started wanting more.
Initially he just joked about it in passing. Then he started hinting at it without much subtlety. Finally, he plainly asked her to just let him fuck her pussy. Victoria refused. She was adamant about not giving her cherry to anyone but her future husband. Soon Tom’s persistent requests to have sex, as in vaginal sex with actual penetration, unnerved Victoria and eventually led to a big ugly fight.
Scared of losing him, more insecure than she let on, madly jealous at the mere thought that Tom might seek from some other girl what she wasn’t giving him, Victoria finally came to a decision. In a desperate effort to keep their relationship intact, she offered Tom a compromise. She would let him fuck her, yes, but not in her pussy: in her virgin asshole. Surprised and overjoyed, excited beyond words at the prospect of penetrating a girl’s ass, Tom promptly took Victoria up on her word.
When the time came for them to have their first anal experience, both teenagers where tingling all over: Victoria with anxiety, Tom with eagerness. Tom licked Victoria’s sweet pussy and rimmed her little pink asshole for almost an hour to get her ready and relaxed, bringing her to a series of toe-curling climaxes in the process. After that, she got on all fours and he applied a generous amount of KY all over her cute tiny pucker, easing his fingers into her anus to coat her tight virginal rectum with lube. Once he had greased himself up too, Tom poked his raging erection against Victoria’s slick rosebud and started pushing.
Victoria whimpered as she felt Tom’s fat glans force its way into her butthole. Despite all the preparation, she couldn’t get over the fear of being ripped apart by his girthy, rock-hard pole. She held her breath as she felt her little virgin asshole getting stretched open by Tom’s invading meat. Even though she knew she should try to stay relaxed, Victoria couldn’t help but tense up as her boyfriend began slowly sodomizing her. Reaching a hand to her clit, gritting her teeth as Tom pushed his fat cock up her ass, Victoria began frigging herself, desperate to mitigate the discomfort.
Behind her bent-over frame, Tom grunted in pleasure, high on the sensation of having his cock inside a woman’s body for the first time. The sight of Victoria tiny butt-ring dilating obscenely to take his cock was the sexiest thing he had ever seen. The feel of her warm gripping tightness clenching around his invading shaft as he eased his way into her untouched rectum was beyond anything he ever imagined. Tom moved very gently inside her, letting Victoria adjust as he fed her inch after inch of his dickmeat. Seeing her masturbating and whimpering as he crammed his cock into her ass, he assumed that she was enjoying the anal penetration just as much as he was. So he kept pushing.
Barely half of his thick length was buried inside her virgin ass when Victoria cried out, begging for him to stop. “Oowww… It hurts! Stop, Tom, pleeeease! Uuuuhh, it’s too big… Pull out, pleeease!”
Panting, crazed by the squeezing tugs of Victoria’s constricting asshole, Tom stopped. Groaning both in disappointment and intense pleasure, he ran his hands all over his girlfriend’s smooth slim body and reached under her, cupping her perky tits and working her nipples just the way she liked.
“This feels so good, babe… Your ass is so hot and tight! Keep touching your clit, it should feel better. I won’t go any deeper, okay?”
“Uuuhh… Okay, but please, pleeease cum fast,” she panted, “I feel like you’re ripping me apart!”
“If you keep squeezing me like this, I’ll cum for sure,” he chuckled, ” and very fast too!”
Wishing only to get it over with, realizing that the uncomfortable cramping sensation in her overstuffed ass actually felt good for him, Victoria started purposely tightening her rectum around Tom’s massive meat. He immediately grunted, tweaking her hard nipples more urgently. Overwhelmed with pleasure, Tom started grinding gently into Victoria’s milking rectum, thrilled by the feel of getting his cock sucked by her tight warm asshole. It wasn’t long before he grabbed harder onto her tits and bellowed out his climax.
As his cock throbbed and pulsed in orgasm, it seemed to Victoria that Tom’s shaft had gotten even bigger in her ass while he spewed his enormous load of cum into her deflowered little hole. Still, to Victoria’s surprise, that felt really good. It was the first time she felt a man’s cum spurting inside her, and it was definitely the best part of her first anal experience. The sensation of Tom’s warm gooey seed flooding her bowels was so unexpectedly erotic that she rubbed her fingers faster over her clit, yelping as Tom filled her rectum with jet after powerful jet of cum. As Victoria cried out her climax, her asshole clamped harder around Tom, coaxing more sperm out of his swollen twitching cock.
From that day on, Tom never lost a chance to sink his boner inside Victoria’s tight little asshole. Strangely enough, Victoria found herself glad that he was so taken with her ass. It was empowering for her to know that Tom lusted after her even more than before, it took away her fears that he might dump her because she was denying him access to her pussy.
Though it was never easy for Victoria to take Tom’s big dick up her ass, in the weeks that followed their first sodomy they gradually managed to make anal sex less uncomfortable for her and even more enjoyable for him. Each time they buttfucked, he managed to get deeper inside her ass, and each time she was more relaxed and less fearful of being split in two as he slowly crammed her butt full of cock. Tom was always gentle as he sawed his thick boner in and out of Victoria’s ass. He didn’t want to hurt her, not after she had gifted him with her anal virginity. He never got to pound her ass the way he had seen in pornos, but he didn’t care. Their slow assfucks were simply heavenly.
It took a while before Victoria could let Tom bury his cock all the way inside her rectum, but eventually, with practice and gradual progress, she managed to take him balls-deep in her ass, much to their mutual stupor. That day Tom shot an incredible load inside her rectum, huge even for his standards. Victoria came screaming on her clit-diddling fingers as Tom’s seemingly endless ejaculation splashed against her anal walls, the ungodly amount of semen feeling like a veritable cum enema. After their climaxes burned out, the two teenagers cuddled for a long time murmuring their love for each other, feeling closer than ever before.