After dating a few months they had great chemistry in and out of bed. A few weeks ago he told her about his anal play fantasy hoping she would be interested but didn't want to press the subject. It never came up again yet he was hoping something might happen.
Dining out on a Friday evening they shared good conversation, great food and almost two bottles of wine. Soon it was time to go and a good thing that her place was only a few blocks away. The night was warm and with their arms around each other they steadied themselves and walked to her house enjoying the closeness of their bodies pressed together. On the way she whispered into his ear that she had a special surprise for him and he immediately asked what it was.
"Oh you will see" she said smiling while her hand squeezed his ass.
Once inside she threw her arms around his neck and they locked into an electric kiss. She led him to the bedroom and they reclined. While kissing passionately she reached down and caressed his already hard cock. He moaned softly with every stroke. Unzipping his pants, she reached in and pulled his cock out. With her fingers wrapped around the shaft she used her thumb to stroke the head. Gently rubbing the flared edge and tracing around it kept him moaning.
Next her thumb rode back and forth over the tip of the soft head. She liked to play with him this way and tonight she focused on it. The wine had made both of them eager to explore and to be explored. Their clothes flew off and she continued where they left off. He was on his back while her thumb continued to circle, squeeze and stroke the pliable head.
His moaning encouraged her. She increased the stimulation making the head yield to her stroking. In a few minutes she felt his precum oozing and used it as lubrication. He tried thrusting his hips into her hand to get her to stroke his cock but she wouldn't let him and said, "Lay still sweetie and I will take care of you".
It was difficult for him to just lay there and take it as her attentions were driving him crazy and making more precum flow from his cock. Just when he thought he couldn't stand it anymore, she stopped and asked him to raise his knees up. He pulled his knees up without hesitation as his mind was reeling from her actions and all that wine. She proceeded to massage his tight balls and took turns rolling them in her fingers until they hung loose. She didn't want him cuming anytime soon.
With a bottle of lubricant she liberally coated her fingers. Next she massaged the area below his balls and slowly inched her way to his ass. She let a finger lightly caress his ass and he let out a gasp. She loved hearing his sounds of surprise turn into moans of enjoyment as she softly massaged his ass. Changing things up, she began tapping his ass. She liked the barely there sensation, the way it teased him and made him push his butt up hoping for penetration. He wanted more and was amazed at how she was in control and making him beg for what she was going to do next.
The tapping alternated with massage to directly massaging his ass. He was getting into each stoke as it gently pulled and stretched his well lubricated ass. Using small circles at the opening, she felt him relaxing and soon worked a fingertip inside. She continued circling and ever so s l o w l y slid her finger up to the first knuckle.
His moaning confirmed that this was a very sensual area. "Do you like this baby?" she asked, his reply was inaudible. "What would you like me to do next?" she said. He answered with an ass thrust into her hand. She slid her finger in deeper just past the opening then hooked her it around the muscle and massaged it. It was an intense sensation and he loved it. In a moment she slid her finger in half way and out, then in deeper. By the next stroke her finger was all the way inside him.
"Oh you are so tight and warm, just let go and enjoy." Soon he started to relax and embrace these new sensations. She could feel him opening up and decided to try something different. She slowly slid her finger out, pausing at the entrance, then thrust it back in deeply. She loved the rush it caused and the sounds he made with each plunge.
He was overwhelmed. His raised his ass to meet every thrust and surprised himself how much he liked it. "Mmmmmmmm...oh your ass is so sexy" she said. "It's so nice and wet". She withdrew her finger and slid another finger inside him. The two fingers took turns sliding in and out and overlapping their penetrations. Sometimes she was pushing one finger in before the other was all the way out.
Then with very little effort she slid both fingers inside and followed with deep rhythmic thrusts which made him moan out loud. Reaching up behind his cock she found his prostate and rubbed her fingers along the sides. Her fingers were circling, stroking up and down and doing figure eights. Massaging his prostate like this was driving him wild. Taking advantage of his semiconscious state she paused and said she would be right back.
The room was dimly lit but he was amazed to see her wearing a strapon when she returned. Instantly he had a feeling of vulnerability. He felt excited and nervous, like he was loosing his virginity. He could not deny his excitement when his cock twitched in anticipation. Her fingers easily slid back inside his ass and now a third finger was about to slide in.
She whispered "When I get three fingers inside...then you will be ready for me to fuck you". His heart was racing as he knew he was helpless to stop her and wanted her take his virginity. Kneeling between his raised thighs she slid three fingers inside him and worked them half way in. Now spreading her fingers he was very open.
Withdrawing her fingers she placed the tip of her lubricated cock against his wet and relaxed ass and said. "Do you want it, in your ass? Then let me hear you baby!"
He could hardly believe his own ears when he said, "Ohhhhhhh fuck me... please fuck me".
She teased him with her cock head, rubbing the tip up and down his ass, gently pressing it in and making him beg. He was trembling and breathing rapidly while they looked deeply into each others eyes and she pushed the head inside him. He let out a long low moan, knowing she was about to start fucking him and he sooo wanted her to.
Stopping for a moment to savor the experience they continued to gaze at each other. Then pressing her hips to him her cock slowly entered him part way. Then withdrawing almost all the way before sliding back in. Each time going deeper until her cock was deep inside him. Followed by long, slow rhythmic thrusts, her hips pushing into his buttocks, stopping for just a moment to grind into him, letting him know she was in complete control.
She continued pumping every inch of her cock into his wanting ass. He mentally escaped into a different space trusting his body to her. Slowly rocking back and forth and gradually building speed until she easily glided in and out of her willing partner. "That's it, take it all," she said as she rode him. As her thrusts increase in tempo and force, his ass gave way to her intensions while his whimpers of ecstasy told her to keep going. And she said, "Oh baby, I love fucking you".
