In the following weeks, Mike and Shelly 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. Shelly was a virgin and she meant to remain one until she got married. As much as she liked Mike 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.
Mike had accepted Shelly’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 Shelly’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 Shelly’s soft lips and warm mouth gave him when they were wrapped tightly around his big cock, Mike 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. Shelly refused. She was adamant about not giving her cherry to anyone but her future husband. Soon Mike’s persistent requests to have sex, as in vaginal sex with actual penetration, unnerved Shelly 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 Mike might seek from some other girl what she wasn’t giving him, Shelly finally came to a decision. In a desperate effort to keep their relationship intact, she offered Mike 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, Mike promptly took Shelly up on her word.
When the time came for them to have their first anal experience, both teenagers where tingling all over: Shelly with anxiety, Mike with eagerness. Mike licked Shelly’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, Mike poked his raging erection against Shelly’s slick rosebud and started pushing.
Shelly whimpered as she felt Mike’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 Mike’s invading meat. Even though she knew she should try to stay relaxed, Shelly couldn’t help but tense up as her boyfriend began slowly sodomizing her. Reaching a hand to her clit, gritting her teeth as Mike pushed his fat cock up her ass, Shelly began frigging herself, desperate to mitigate the discomfort.
Behind her bent-over frame, Mike grunted in pleasure, high on the sensation of having his cock inside a woman’s body for the first time. The sight of Shelly 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. Mike moved very gently inside her, letting Shelly 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 Shelly cried out, begging for him to stop. “Oowww… It hurts! Stop, Mike, pleeeease! Uuuuhh, it’s too big… Pull out, pleeease!”
Panting, crazed by the squeezing tugs of Shelly’s constricting asshole, Mike 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, Shelly started purposely tightening her rectum around Mike’s massive meat. He immediately grunted, tweaking her hard nipples more urgently. Overwhelmed with pleasure, Mike started grinding gently into Shelly’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 Shelly that Mike’s shaft had gotten even bigger in her ass while he spewed his enormous load of cum into her deflowered little hole. Still, to Shelly’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 Mike’s warm gooey seed flooding her bowels was so unexpectedly erotic that she rubbed her fingers faster over her clit, yelping as Mike filled her rectum with jet after powerful jet of cum. As Shelly cried out her climax, her asshole clamped harder around Mike, coaxing more sperm out of his swollen twitching cock.
From that day on, Mike never lost a chance to sink his boner inside Shelly’s tight little asshole. Strangely enough, Shelly found herself glad that he was so taken with her ass. It was empowering for her to know that Mike 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.