Eyeing the dildo, Willa furrowed her brow a bit. “You’re such a guy,” she laughed. “I don’t think most women would pick out a dildo that looks like that one. But, if you think we’re ready for it, I’m game. Does it vibrate or do any tricks? Whistle? Squirt?”
“Uh…”
She cracked up. “I’m just kidding. Why don’t you show me what you have in mind?”
Her question had an instant impact on Jackson, and he was already at full staff and ready to play. He set the toy and the lube on the bed next to Willa and pulled her into his arms again. “I’ve played with your ass enough now that I think you’re ready to take me. Are you prepared for this?” he asked as he nuzzled her neck. He could see goosebumps break out on her arms and thought that was a good indication of her acceptance.
“Yes,” she replied in a breathless voice. That one little word held a lot of desire.
“Get on your hands and knees,” he ordered.
Jackson grabbed a condom and popped the lid on the lube. Willa watched over her shoulder as he sheathed himself and then poured lube into her butt crack. He used his fingers to gently massage her, slowly probing the tip of his finger inside. He added more lube as he pushed up more deeply, always retreating to lube up his finger.
Willa sighed with pleasure as this massaging and probing went on. Then with a little start, she felt a second finger enter her. It caused a tiny, momentary sting that immediately went away as Jackson spread more lube around. All the while, he stroked her with his other hand, touching her neck, her breasts, and finally her clit. All the while, he continued to stretch her rear entrance.
“Remember to stay relaxed. I won’t ever push you too hard. If it hurts, say so, and I’ll stop, okay?”
Willa groaned, “It’s fine. I promise. Don’t stop. I like this.”
Chuckling, Jackson pulled out his fingers, and this time he slowly, ever so slowly, inserted three of them.
“Oh!” Willa gasped.
“Too much?” he asked in a worried tone.
“Um, just more than I expected. Don’t stop.”
So, Jackson moved his three fingers in and out of her slowly and carefully. Her tight ring of muscles squeezed him and then finally relaxed. “I think you’re ready,” he declared. “Is it alright to go ahead?”
“Yes, please,” she moaned.
So, Jackson removed his fingers and brought his throbbing dick to her. He never stopped manipulating her clit with one hand as he carefully positioned himself. “Now take a deep breath in and tense up your muscles as hard as you can. Good, like that. And now quickly let it go and breathe out,” he told her. As she softened, he slowly guided himself into her body.
Willa’s eyes practically rolled back in her head at the sensation of Jackson entering her this way. She could feel the warmth of his body against her as he finally pushed all the way inside. He didn’t move yet, letting her relax enough to accommodate him.
“Are you alright?” Jackson asked, his voice sounding strained.
Breathing heavily, Willa shook a little as she answered, “I had no idea it would feel like this. I’m fine, but don’t make any sudden moves, okay?”
Jackson bent down and kissed her shoulder. “You set the pace, sweet cheeks.”
Willa chuckled at his endearment.
Finally, Willa indicated that she was ready, and Jackson began slowly, lovingly moving in and out. “Wow,” she breathed.
“Are you ready for the other guy now?” he asked. He was using all of his concentration to make sure he didn’t come too soon and ruin her experience. “The dildo’s been washed. Do you need some lube on it?”
Snorting, Willa replied with a smile in her voice, “Hardly. I’m positively dripping down my legs. You have no idea how turned on I am right now. Hand it over.”
Jackson chuckled and passed the dildo to her, saying, “You are absolutely the woman of my dreams, Willa. God, I’m so in love with you.” He kissed her back again.
Willa maneuvered the phallus into herself and they both gasped simultaneously as they felt it meet up with Jackson, bumping him deep within her.
“Use the switch on the base, and it’ll vibrate,” he told her, his voice raspy with arousal.
“Ohh, God,” she moaned. “I think I’m in heaven right now. I’ve never felt so completely… so totally… aahhhhhgg!!”
“That’s amazing. I feel it vibrating me through you,” he moaned. “I’m going to pick up the pace a little now, is that okay?”