Jessie’s only answer was a weak smile, but she leaned into his caress. She didn’t look entirely convinced, but nor did she seem keen to dwell on the issue. “Can you hold me? Please?” she asked softly, making to turn herself over once Justin finally withdrew his still stiff erection from between her legs.
With one firm hand planted squarely on her back, though, Justin brought the roll to a halt almost before it began, his intervention drawing a confused look from the teenager. “I’ll hold you all night, Jes,” he reassured her, “but I don’t think we’re done just yet.” As he nudged her back into position, Justin was unable to resist letting his eyes fall to Jessie’s freshly deflowered womanhood, drinking in that magnificent view. Her entrance was swiftly drawing closed after his departure, but all the same he could see a steady trickle of his cum leaking out, its normal pearly white stained to a hue of rosy pink. “A girl as wonderful as you deserves a memorable first time, not just a quick little tumble. Besides, there’s something else I think we should try…”
“What? What do you… OH!” Jessie squeaked like a cornered mouse as he brushed the tip of his cock against her puckered rear entrance. His grin only grew wider as the teen’s already flushed cheeks shot scarlet.
“That’s right, cutie. You’ve put so much work into this glorious ass, it’d be such a shame to let it go to waste.” Justin let his free hand drift to the girl’s rump, kneading one cheek briefly before pulling it gently aside to get a better view at his target.
“But, doesn’t… I heard…” There was no mistaking the way Jessie gulped at the thought of what her partner had in mind, her voice trembling. “People say that it hurts.”
“It depends on the girl,” Justin hedged, continuing to massage his partner’s rear as he made his case. “Some really like taking it up the ass.” That’s true, he thought to himself, more or less.
“I don’t know…” Jessie was biting her lip again as she gazed up at him, the effect undeniably adorable on her already gorgeous face.
“I think we should try,” he told her, trying to strike the perfect balance between confidence and encouragement. “If you don’t like it, we can always stop.”
That promise seemed to do the trick. “Well… I guess so… if you want to…” Jessie didn’t look eager, exactly, but it was enough for Justin. With a little luck she would enjoy it once they got started. And if not, well, she could always be taught to.
“That’s a good girl.” Not wanting the shy blonde to back out, he slid one hand beneath her hips to give her clit a little tweak. Her eyes closed and a little shudder of pleasure rippled through her body, whether from the words, the attention, or the combination was impossible to say.
“Please be gentle,” Jessie pleaded as the hand shifted back up to her ass.
“Of course,” Justin promised, her words bringing back echoes of his earlier resolution to keep his instincts in check. With one hand he kept a firm grip on the teen’s hips while the other worked to line himself up. “You’ll want to relax, otherwise this will hurt.”
“Okay,” she whispered, not looking all that relaxed. Justin didn’t stop, though, working his cock until the crown was resting against her starfish. Thankfully his shaft was still thoroughly drenched from her cunt otherwise there would have been no hope of getting in her without lube and he had none handy.
Justin’s first tentative push against Jessie’s stubborn anal ring drew a sharp gasp from the teen despite the fact that it lacked anywhere near the force required to actually enter her. His second, slightly harder, attempt drew another gasp followed by a demure little whine. For a long while their dance continued in much the same vein, Justin probing gently but with increasing force at the blonde’s rear entrance to get her used to the idea and sensation of what was to come next while Jessie fought to suppress her instinctive reactions, jumping a little less each time she felt his approach.
When her lover finally made his move and pushed the crown of his cock past Jessie’s sphincter the following shaft made it less than an inch into the teen before her tight passage clamped down around him. The girl’s yelp at the invasion of her rear had to be loud enough for Lily to hear in the room next door and then some, but beyond that lone cry any lingering reservations were kept to herself. No longer needing to guide his cock by hand, Justin reached back under his lover’s hips to seek out her clit. As tight as she was there was no getting around the fact that having her ass broken in would hurt like all hell, so he was going to need to keep her too distracted by pleasure to complain. It seemed to work well enough. The first tweak he gave Jessie’s sensitive little button upon finding it caused her hips to buck back against him and in so doing provide him the opportunity to slide a little further up her chute.
Over several long minutes Justin patiently worked his way deeper and deeper into the teen’s ass, savouring the experience and taking great care to minimize his partner’s discomfort. There was only so much he could do, though, and judging by the way she whimpered and whined it was clear Jessie was struggling to take his girth. Still, though, she soldiered on, and the longer they kept at it the less and less strained her voice sounded.
Justin, on the other hand, was in heaven from the start. It was hard to say which was more blissful, the way Jessie’s alluring body trembled beneath him or the way her vice-like ass clenched down on his cock in a vain effort to expel the invader. During their time together Gwen had seldom consented to letting her boyfriend take her up the ass and had never been terribly active to start with, so it had been many a year since Justin was last able to enjoy the sort of bliss he felt at that moment. There was just something about a sexy young athlete’s ass that was… incomparable.
Scarcely half his length had disappeared up Jessie’s rear before the first quiet moan signaled her increasing acceptance, even appreciation, of what was happening. “You like that?” Justin asked, leaning forward across her back even as her hips started to rock ever so slightly against his own. While he continued to tease at her clit with one hand, his other slid up and across her smooth back until he was delicately pulling aside her soft golden hair to tuck it away behind the ear he was whispering into.
“It… oh… it hurts a little,” she murmured, her voice hazy as if she were struggling to concentrate on something that demanded more attention than she had to give. “But… it’s also… kinda nice…” The adorable expression on the teen’s face brought a smile to Justin’s, what with her little nose all scrunched up and her eyes squeezed shut. Before straightening back up he took a moment to plant a long kiss on her faintly flushed cheek.
“I’m glad.” He whispered. As he rose, Jessie’s new lover let his fingertips lazily trace their way down her spine, loving the way that act made her body shiver and her rectum clutch tight at his cock. When he eventually ran out of spine, his hand drifted to one side where it came to rest possessively on the teen’s rump. For a few minutes he pawed and kneaded at her firm curves, luxuriating in the way his lover moaned at his every caress.