This time when Jessica went to the pool she didn't bother with the white bikini top she'd been wearing for her swims. She waited for Tommy in the pool, arms stretched out along one edge of the pool, mermaid tail and tits floating near the surface. When Tommy arrived at the pool deck, he stopped and stared. It was the first time he'd seen bare tits in person.
"Come on it," Jessica said, "the water's warm as usual."
Rather than cautiously wade it via the steps as he usually did, Tommy went directly to the side of the pool opposite Jessica and slipped into the water. Jessica smiled at the subtle change in his behavior.
When they took their customary mid-swim break, sitting on the edge of the pool, Jessica was surprised when Tommy placed a hand on hers and asked: "Can I kiss you?"
"Yes," said Jessica. They leaned in and their lips met.
When they parted, a bashful Tommy admitted: "That was my first kiss."
"Then here's your second..." said Jessica and she wrapped her arms around Tommy and pulled into a more passionate kiss. Tommy hesitated for a moment, mostly out of surprise, before reciprocating and wrapped his arms around Jessica. Several more kisses followed, Jessica's bare breasts pressing against Tommy's bare chest.
After this brief making out, Tommy looked flustered. Jessica could see the bulge in his wet trunks. Then Tommy abruptly dove back into the pool, swimming away. Jessica wasn't sure if he was scared or trying to be playful. She dove in as well, swimming after him. Jessica realized Tommy seemed to be swimming with more vigor than usual. She let him make a couple laps before chasing him underwater and tapping him on the foot, as if to say "tag!" Then she swam away. Tommy followed, and Jessica let him catch up and touch her tailfin to tag her back. This went back and forth a few times.
Then Jessica decided to be bold. Swimming after Tommy with more speed, not holding back this time what her tail was capable of, she caught up to him again. This time, instead of tapping his foot, she grabbed his swim trunks and yanked them off.
Tommy promptly surfaced, sputtering, and stumbled through the shallow water before sitting on the pool steps. Jessica slowly swam after him.
"What...why..." Tommy said, fumbling for words.
"I was tired of being the only one skinny dipping," explained Jessica. "Besides, I've seen you straining for days," she added, stroking his erection. Like his looks, Tommy's endowment was pretty average.
Tommy grabbed Jessica and pulled her into a hungry kiss, their naked bodies pressing together.
"Yesterday...you...after our swim...I saw you..."
The realization that Tommy had watched her masturbating turned Jessica on.
"Tommy, you're such an tightly-wound young man. Let me help you relax..." Jessica been kissing her way down his chest.
"What do you...oooooooooh..."
Jessica took Tommy's erection in her mouth and began to give him his first blowjob - underwater, no less. Tommy wasn't sure how to react at first, but finally leaned back on the steps and rested his arms on the side of the pool. Tommy was lost in the bliss. It didn't take long before he started to climax. Jessica kept going until he was finished then swallowed, before finally coming up for air. She was impressed by how long she'd held her breath.
Tommy looked at her with a slightly dazed expression, but smiling more than she'd ever seen before. She cozied up against him, her back to his chest.
"Now it's my turn," she said. She directed his hands to her chest. "Be a dear and play with these, wont you?"
Tommy fondled Jessica's breasts while she masturbated, then held her as she shook with an orgasm.
The two held each other in the water for some time after that.