"So, if I win today, I want to tie you up and play with you." said Kerry, her eyes twinkling as she winked at Derrick.
The idea of being totally at her mercy was both frightening and breath-taking... but he had his priorities too, "If I win, I get your ass cherry." And he leered at her. He was dying to take her in the ass ever since she'd had him, and although last bet he'd lost had ended up being thoroughly enjoyable, he still hadn't been able to stop thinking about winning. After all, Kerry did have a fantastic ass, and since she'd taken his cherry it was only fair that he took hers.
This time, as they watched horse-race, she climbed onto his lap and let him play with her tits as they watched, her ass grinding down into his dick. He could feel her firm cheeks between the clothe that separated them and was very very hard already; pinching her nipples tightly he listened to her moan. There was also something exciting about losing, he'd have no control over what she did to him and really no say either... once he got her ass it might be something interesting to try out. Or maybe he'd go online and find something else to push her boundaries a little... even if it was just a different location or something that she hadn't come up with yet. He'd really like to surprise her with something.
Kerry could feel his dick digging into the crack of her ass, it made her pussy leak with juices as she thought about the fact that she might be losing her anal virginity. After he'd ended up enjoying it so much she'd wondered what it felt like, especially after his tongue had licked her anus last time. It had felt so incredibly good, so unexpectedly sensational, and she was actually feeling rather excited to have him fuck her there. Still, tying him up would be fun too, and then she'd even get to do him in the ass again if she wanted. Or she could just tease him mercilessly; she smiled as his fingers played with her nipples, teasing him for a very long time before getting him off would be awfully fun.
But it wasn't something that she would get to explore this time... his horse passed the finish line first easily.
Derrick's hands gripped her tits hard as he whispered in her ear, "Your ass is mine."
************************
Upstairs he put her in the exact same position that she'd had him in for the taking of his ass cherry, a pile of pillows in the center of the bed to go under her hips, and one to go under her head. Because she was so nervous he started out by massaging her back and reaching around to cup her tits, squeezing them gently and rolling her nipples between his fingers. After all, he wanted her to enjoy this. Once he felt her tension starting to release he lubed up on of his fingers and began to press it into her ass.
Shifting her hips, Kerry felt the finger begin to enter her... it felt very strange. And very big. Squeezing and wriggling she tried to adjust, feeling it go deeper and deeper into her body. It hurt a little, but not as bad as she might have though... mostly it just felt very very odd. A kind of pressure that she felt like she should be able to relieve but couldn't.
Behind her, smiling, Derrick picked up the vibrator that he'd laid next to her legs and started to press it into her pussy as his finger wriggled in her ass, turning it on to its lowest level. Kerry moaned as something unexpectedly entered her wet pussy and started to buzz, it made her ass clench down on his finger again in reaction. That felt incredibly good... as he pressed the vibrator all the way in and started to fuck her ass with his finger she felt like she was stuff full. As a second finger entered her ass she groaned as it stretched, and he turned up the vibrator a notch. The pleasant sensations of its teasing vibrations went a long way towards distracting her from the slight discomfort in her ass.
He enjoyed watching his fingers invade her tight slick hole, and even more enjoyed the way her ass moved and humped against them as the vibrator really started to get to her. Pumping his fingers in and out of her ass, he could feel the vibrator humming against them and wondered what it was going to feel like against his dick. Probably fantastic. Grinning in anticipation, he tried to spread his fingers a little, stretching her open even more... groaning, her hips shifted again.
Turning the vibrator up another notch he removed his fingers from her ass and started to lube up his dick. Kerry wanted to tense up as she felt his hands caress and grip her ass cheeks, but the vibrator was doing its work too well, she couldn't tense up for too long because of the way it buzzed inside her. Putting the tip of his dick to her ass, he marveled at the fact that his large round mushroom head was about to make its way into that little crinkled hole. Pressing in, he watched as the wrinkles in the hole smoothed out as her ass opened up, until it suddenly popped over the head of his dick and closed tightly around the shaft.
Both of them gasped; Derrick because this new orifice was so incredibly tight and exciting, and Kerry because her ass was now stretched very wide. Groaning, she wriggled her hips, his dick felt huge inside of her and she knew that he wasn't even very far in... the fact that she had a vibrator in her pussy wasn't help the over-whelming feeling of fullness in the lower half of her body. Derrick's dick twitched as the vibrations played over his sensitive head, he turned up the vibrator another notch and groaned, shoving his dick in another inch. Arching her back as his dick began to work its way into her tight hole, Kerry was having trouble reconciling the pain and the pleasure in her body; they seemed to be twining together in an unholy mix that made her pussy spasm.
Slowly the vibrations spread over Derrick's entire dick as he worked it into her ass, and with just the last two inches outside of her body he couldn't take the slow pace anymore. With an apologetic groan he pressed all the way inwards, shuddering as her ass convulsed around his invading member. Kerry jerked backwards as the last of his dick buried itself in her body, causing him to thrust even more deeply and roughly than he'd meant to; but the little wave of pain and discomfort it caused was almost nothing compared to the pleasure. She felt completely full, her entire lower region stuffed and buzzing as the vibrator was pressed more firmly into her pussy by his position behind her.
Moving her hips in a circular motion, she made both of them moan as his dick stirred her insides, and he began to pull out of her ass to begin steadily thrusting in and out of her tighter hole. Humping her backside, he ran his fingers over her back and down to her hips, trying to find the best placement for his hands; every thrust of his hips pressed the vibrator into her pussy along with his dick so that it was like there were two cocks each fucking one of her holes. And one of them happened to be buzzing erotically.
Kerry pressed back harder against him, feeling the strangest sensation in her belly as he fucked her, like her entire lower region was tensing up for a fantastic release. As her hips moved back against his body he hunched over and reached under her, wanting to see if he could feel her tits... to his delight he could and he grabbed a hold of the swaying globes and squeezed. Shuddering, her ass rippled over his dick as he began to knead her sensitive tit flesh with his fingers, pinching the nipples and tugging on them. Thrusting harder, he started to really pound into her ass, sliding in and out of her slick hole with complete lustful abandon.
With the vibrator buzzing in her pussy Kerry actually reached climax before him, crying out in passionate rapture as his dick continued to pound her asshole. Every thrust drove her ecstacy higher until she was shaking with the intensity of it... her ass gripped him hard as his dick began to pulse inside of it. She could feel every spasm as each spurt of cum passed through his dick, making the bottom of it pulse and swell against the rim of her ass before it spilled into her dark hole.
Reaching down, she turned off the vibrator in her pussy before its tremors could become painful.
