Jennie exhaled to steady her nerves, then slowly extracted her finger from Lisa's mouthwatering ass. Grabbing the toy from the silver pouch she'd left behind her hip, she pumped yet more lube onto her fingers to thoroughly coat its length from tip to base. The first trainer was a scant four inches long and merely one inch at its widest point, so she had confidence her precocious partner could endure its insertion. Despite her intermittent bouts of anxiety, Lisa clearly craved this experience, and Jennie's touch.
Unfortunately, Lisa's fear of misstepping was every bit as transparent as her desire. More than once, Jennie had sensed Lisa's fear of reacting in a way that would cause Jennie to stop what she was doing, if not leave altogether. So although Lisa had promised not to hesitate with her safe word, Jennie couldn't shake her concern about her young friend's stubborn need to please.
Knowing she'd never forgive herself if she hurt the woman on her lap, Jennie conducted one last check-in. "Lisa..." She parted Lisa's shapely cheeks with her left hand and positioned the tip of the plug against her anus with the right. Painting deliberate, suggestive circles around the rim, Jennie said, "If you do need to use your safe word, that doesn't mean our night together has to end. Not if you don't want it to. Got it? I need to make sure you know that you're allowed to push pause. It won't freak me out or make me leave. I promise." To prove she wouldn't stop until Lisa commanded it, Jennie applied pressure to the base of the plug, savoring Lisa's moan when her butthole opened up to suck the tip inside. "Do you understand what I just told you?"
Lisa gave a semi-frantic nod. "Don't be afraid to use my safe word. I won't, I promise." She reared back to try to force the toy deeper, whimpering when Jennie prevented the attempted takeover by moving with her. "Please, Jennie. Fucking do it already. This foreplay is bullshit."
Heady from her power over sweet, sexy, creative Lisa, Jennie ventured farther inside her slim rectum, coming to a stop as Lisa groaned at the introduction of the widest point. "Relax," she murmured like a broken record. "Relax, darling, and bear down." She felt Lisa consciously heed her advice and beamed as the plug continued its unhurried journey into her anal passage. "That's it! You're doing an amazing job, sweetheart. I'm so proud of you."
Lisa shuddered as the plug slid the rest of the way inside and her anus constricted around the narrower base. "Ohh..." she breathed. Hips jerking, she humped Jennie's lap in a blatant hunt for friction. "That's...it feels..." Hoping to inspire some elucidation, Jennie gave the plug a glacial twist, wiggling the base carefully from side to side. Lisa's fingers twitched on the comforter, and she moaned. "Unreal."
Jennie smiled, chest tight from the unmitigated joy of seeing Lisa experience that much ecstasy. Her satisfaction wasn't about having caused it so much as being there to savor the result. Seeing Lisa happy made her happy. Period. Stirred by feelings she didn't want to entertain, Jennie fondled Lisa's labia while removing the plug halfway, then driving it back in. "Rub your clit, honey. Keep that pussy slick for me while I'm fucking your ass."
"Fuck," Lisa whispered, trickling hot juices onto Jennie's roving fingers. "Maybe...get the next plug. Before..." She gasped. "Before I come...again."
Lisa's right hand moved between them, bumping rhythmically against the juncture of Jennie's thighs. Wishing she'd removed her pants to benefit from the modest friction, Jennie disregarded her rising hunger to attend to Lisa. She reined in her libido, then eased the first plug all the way out.
"As you wish," she said, trading the toy in her hand for the next size up. She applied a generous serving of lube to the new plug — all four and a half inches of it — before placing it between Lisa's firm cheeks. "Tell me when."
