Taking it to the Next Level
Emily had been seeing her boyfriend, Jack, for just shy of a year. They had started off a classic high school romance: kid meets girl, sparks fly, and soon enough, the couple are sneaking off for make-out sessions in hallways.
But as their relationship matured, the couple began to explore their more physical desires. Emily had always been curious about sex, but she had been too shy to ever actually take the plunge. When Jack suggested they try anal sex, Emily was hesitant at first. After all, she had heard a lot of horror stories about how painful it can be. But Jack was patient and reassuring, and eventually Emily gave in to her curiosity.
One night, after a long day of classes, Emily decided to take it to the next level. She had already been experimenting with Jack by incorporating a few toys into their bedroom play. With her newfound confidence, she was ready to try something new.
When they arrived at Jack’s house, Emily stripped off her clothes, revealing a collar and leash around her neck. She approached Jack, who sat on the edge of the bed, and knelt in front of him. She kissed his neck, then slowly pulled down his boxers. Jack gasped as Emily revealed his erect penis, and she smiled up at him, slowly moving her head forward for a deep kiss.
Emily’s tongue glided along Jack’s shaft, slowly and methodically as she worked her way down towards the base. When she finally reached the tip, she eagerly took him into her mouth, bobbing her head up and down in a slow and steady rhythm. Emily could feel the pleasure radiating through her body, and the sensations only increased as Jack’s hips began to thrust in tune with the rhythm set by Emily’s mouth.
Jack’s breathing was heavy, and Emily could feel her own arousal growing. She loved tasting him and feeling him grow even larger with each stroke of her tongue. She wanted to make him beg for more, and that’s exactly what she did. She circled his shaft with her tongue before stopping at his perineum, pressing her tongue lightly against the sensitive area as her hands slid up and down his length.
Jack was panting uncontrollably, shouted for Emily to take him all the way. She smiled up at him, enjoying the look of pleasure on his face, and without hesitation, Emily slowly pushed her lips around his tip and took him into her throat.
The sensation was pure bliss for both of them, and it wasn’t long before Jack was begging for more. Emily was more than happy to accommodate, and soon enough, Jack was pushing Emily onto her back, ready to take her anal virginity.
He began by carefully pushing his finger into Emily, letting her get used to the sensation of being filled before he added a second—then a third. His careful and gentle movements were such a stark contrast to his now fervent thrusting, and Emily could feel her entire body trembling with each thrust. She was so close to the brink of orgasm, but Jack had no intention of letting her go that easily.
He increased the speed of his thrusts, pushing past Emily’s tightness and stimulating the nerve endings around her anus. Emily felt a wave of pleasure spread throughout her body, so intense that she could barely contain her screams. Jack kept up his rhythm, and soon enough Emily was overcome with orgasm, shaking and quivering beneath Jack as he continued to thrust until he was ready to join her.
When the two of them finally lay still, Emily was exhausted and content. She had taken it to the next level, and she was glad she had done it with Jack—someone who had proven to be patient and respectful of her boundaries. Emily could only imagine how many more amazing experiences they would share together, and with that thought in mind, she drifted off to sleep in Jack’s arms.