Blackmail Birthday Present

He didn't want to acknowledge it, and the only way he could think to avoid that was to just hold still in her ass. He knew that anal sex wasn't supposed to be comfortable right out the gate for a woman. He didn't want to stop now that he was inside, but a part of him wanted her to find some enjoyment in this.

An idea struck Ted. Still buried to the hilt he reached up and grabbed the massaging showerhead and set it to pulse mode. His left arm wrapping around her torso, he brought the head down, pointing it at her pussy.

A loud moan of pleasure escaped from Bailey's lips immediately--he definitely found her pressure point. He held the showerhead in place as he pulled out again. The girl's moans of pleasure continued as the showerhead pulsed repeatedly over her clit, driving him wild as he started to actually fuck her ass.

From what he could tell, any pain she was still feeling from being buttfucked gave way to the pleasure she was experiencing. As her breathing became more rapid, so did Ted's thrusting.

"Squeeze my tits," Bailey suddenly yelled out.

Ted was so taken aback by it he stopped fucking and just held her. In his slackening, the showerhead stopped massing her pussy.

"Wait, what?" he asked.

"Point the showerhead back right, start fucking me again and squeeze my tits," she replied through clenched teeth.

He heard the teen loud and clear this time, another loud moan informing him he got his aim right again as he started thrusting into her ass with renewed fervor. His left hand reached up to grab her right breast, fingers pinching the nipple as he felt her shudder beneath him.

"So. Close." she panted.

Ted squeezed her breast a little harder and leaned in as he tried to pick up the pace.

"Cum for me slut, cum from your first assfuck."

He could never be sure whether it was the squeezing, or the dirty talk, or the showerhead itself that did the job--as soon as he said the word 'assfuck' Bailey let out another high pitched cry. It wasn't like the cries of pain, it was something raw, animalistic, followed by more cries as her whole body shook with orgasm.

Ted dropped the showerhead, the rattle as the metal impacted against the marble echoing through the bathroom. Both arms wrapped around the cumming girl, he grabbed and squeezed both her tits as he drove into her ass as rapidly as he could. The undulating of her body, her cries of pleasure, and most importantly her ass seeming to squeeze around him as she came finally set him off as he plunged deep into her ass and felt himself cumming once more, his own loud grunt joining with her moans of pleasure.

After his outburst this morning Ted wasn't sure how much he was really filling her ass with cum, but that didn't matter. His right hand ventured down to her pussy again, trying to find the little nub that the showerhead had done such good work on. Finding it he rubbed it furiously, hoping to extend her own orgasm even as his subsided.

It could have been just seconds, or perhaps it was minutes or even hours, but eventually the two blackmailed lovers came off their respective highs. Pulling out of her they both collapsed to the tiled floor of the shower, catching their breath as the water still cascaded over them.

Ted looked around the shower as Bailey was practically laying in his lap. Besides the pulsing showerhead he noticed the bar of soap had fallen to the floor as well. Grabbing the showerhead and the bar of soap, he started to get a lather going again. Thinking about it for a moment he frowned and set both back down.

"Go ahead and finish showering. I'll be downstairs."

He began untangling himself even as Bailey looked at him confused. She didn't say anything when he grabbed a towel and started drying off. Standing herself, she watched as he left the bathroom and headed out back to the main part of the house.

When Bailey finally finished showering and headed downstairs, she saw Ted sitting on the couch wearing the bathrobe. Remaining naked, she sat down in front of him on the coffee table once more. "Everything fine?"

Ted nodded slowly to her in response.

"Liar," she teased. "Seriously though, what's wrong?"

He shook his head and looked away from her.

"I feel kinda bad Bailey. I let my lust and desire take over and didn't care if it hurt you."

A look of understanding appeared on her face and she smiled warmly to him. She stood up and moved to sit in his lap.

"Look, I know this is tough for you. It's tough for me too Ted, but to be honest, I'm glad you did."

"Why?"

"Because, it meant that you were doing what I asked, trying to disconnect our having sex from how you view me. You know I consider you a father, and I'm sure you consider me a daughter. There's no way for this to be easy for either of us. But at the same time Ted, I think it's best if we try to make some good of a bad situation. A little enjoyment is at least better than us hating every second of this."

He nodded to her slowly. "How's your ass?"

Another smile crossed Bailey's face. "The truth?"

Another nod from Ted.

"Well, it hurts, and yes, I knew anal was going to be painful. But you know what, I'm glad it was you, who at least had some concern for me, and wanted me to feel pleasure instead of some jerk my age who just thought he deserved the privilege. And to be honest Ted, that was the best orgasm I've ever had in my entire life."

"Is that why you wanted me to grab your tits?"

"Yeah, my boobs are rather sensitive. Some nipple play when I'm close always helps to get me off. I think it's funny though that my best orgasm ever came while being buttfucked." Bailey laughed like a much younger girl at that moment. "Ted, thank you for the best orgasm ever. I hope whatever it is that the blackmailer's expect us to do the rest of the evening will be just as fun." She leaned forward and gave him a quick kiss on the lips. "So what's next?" she asked, a playful grin on her face.

"How about a movie?"

She crawled off his lap and went over to the movie library by the TV.

"Get in the recliner Ted."

He got up from the couch and got into the recliner--it was fairly obvious what she planned as she stuck a movie in the blu-ray player and grabbed the remote. Bailey moved to sit in his lap, nuzzling up against his chest.

Ted was confused by her choice of The Hobbit as something to watch, but for nearly three hours it was rather nice to just lay there in the chair with her sitting in his lap. His arms remained wrapped around her the entire time, and she occasionally wriggled playfully, but it was just a rather nice, relaxing time.

It was nearly six in the evening when the movie finished. Grabbing the remote Ted turned the TV off and hugged Bailey.

"Hey, would you be able to run home?" he asked the teen.

"Sure, what's up?"

"Oh, I'd just like it if you changed into something really nice. Perhaps maybe a few outfits, you know, something nice, something naughty."

She turned her head to look at him. "Sure, I can do that. How much time?"

Meet me back here at seven, I'm going to go out and get us some dinner.

She climbed off of him and smiled back. "Sounds like a plan. I assume after dinner we're going to finish off whatever it is that we have in store for the rest of the night?"

"We will."

Bailey quickly got dressed, and as much as he thought about staying to watch the process, he too got up and headed upstairs to get dressed himself. By the time Ted came back down Bailey was already gone.

The hour passed quickly. Ted stuck to his word, ordering Chinese food for dinner as well as doing a little bit of grocery shopping. Besides picking up a few of the food items he needed, Ted went to the pharmacy section, grabbing a box of condoms just in case.

He arrived home with about ten minutes to spare, having enough time to set the table for dinner before the doorbell rang. When he opened the door for Bailey his heart wanted to skip a beat--it was as if the teen had read his mind.

Bailey stood in the door in thigh-high stockings, a flirty black skirt, and a white men's dress shirt that wasn't tucked in. Her backpack was with her again, presumably with more clothing. As she passed him entering the house he noticed that she wasn't wearing a bra, and he wondered if her panties were missing as well.

She set the backpack down on the couch and moved to the dining room. Dinner was uneventful, neither of them spoke, instead just eating their meal. Without him asking she cleared the table while he went upstairs, grabbing her laptop and plugging it in once more in the dining room. Pointing it to where he was sitting he waited until Bailey finished putting the dishes in the washer. The girl looked over at him as he had everything set up.

"I take it the next round is starting."

Ted nodded. He knew that the blackmailers would want to see this next bit.

"Over my knee slut."

Bailey raised her eyebrows and smirked. She moved to the right side of him and leaned over his legs, her ass pointed right at the webcam on her laptop. Ted reached out with his right hand and moved his hands up and down her stockings before moving his hand up to lift her skirt. He was right, she was sans panties.

"You've been naughty today, making me cum after only being in your mouth for a few seconds, cumming while I took your anal virginity. That calls for a spanking."

She remained silent, and he decided to change that as his left arm moved over her back to hold her as his right hand came down and smacked her ass.

She breathed out a little heavier, but failed to make a sound. He enjoyed the feeling of smacking her ass, the slight red mark that appeared for just a second before vanishing. Ted never really spanked Emma, his wife generally took that duty when it came to it and once she died Emma had pretty much outgrown it. He did spank his wife as foreplay when they were younger, and they both enjoyed it--it was probably why he didn't think of it as punishment but as something sexual.

Another smack came down on the pale teenage ass, followed by two more. The last smack finally got a slight yelp out of the teen. He looked at her ass--it was starting to look a little more red, though no hand prints were sticking. He continued his smacking of her ass, six more hits--a yelp with each smack.

He rested his hand on her ass for a moment, just rubbing the soft skin before he raised his hand once more. He delivered eight more smacks, harder and harder every time--the last smack by far the hardest. It was also the smack that got the loudest cry from the teen. He lifted his hand just slightly off her ass, feeling the heat coming off of it before moving to look--the redness was staying with her this time. "That's all. I've always wanted to give you birthday spankings, and now you've had your eighteen."

As she rolled off of him to stand back up, instead of pain on her face from the spanking she had a large smile. "Well, thank you for the birthday spankings then, though I thought the tradition went the other way."

He laughed and shook his head.

"That's not happening. So, how about you change into something a little more naughty, though keep the stockings and your tennis shoes, and leave your pussy exposed."

She quirked her eyebrows up at him, a little surprised by the last comment but she nodded and went to grab her backpack, heading into one of the back rooms to change. She wanted to surprise him after all.

He looked at the clock, quarter-to-eight. He grabbed one of the chairs from his dining room table and set it next to the coffee table. Moving the laptop into place, he turned it to face the chair. He went back to the shopping bag and pulled out the little brown paper bag he had and set it on the coffee table next to the chair.

She came back out and he was floored. She kept with the tennis shoes and the thigh highs, and did exactly what he asked in keeping her pussy bare. For her torso she came out wearing a white corset--something he was a bit surprised she managed by herself until he saw the hint of a zipper on the side. It made the girl's torso even smaller, but left her breasts exposed for him to look at as well.

"Have a seat slut."

She smiled. It was a definite hint that this was more about his enjoyment than hers once more. She sat down in the chair and he motioned again.

"Legs over the arms please."

Once again she obeyed, displaying herself completely to both him and to the camera.

"Alright, this is something they'll be expecting, otherwise I wouldn't ask. I'd like you to masturbate with the object in the bag."

Bailey had a look of curiosity on her face as she reached for the bag. Her eyes went wide as she pulled out the small cucumber. Ted's face reddened as he saw her looking at it.

"Sorry, saw it in a video once and ended up watching it a few dozen times. If they seriously know, they'll be expecting it."

She laughed at his feeble explanation.

"Hon, they've made me do similar stuff, so I can live with it."

She moved the cucumber to her right hand and leaned back in the chair. Closing her eyes, she moved the gourd down her body and started rubbing it along her clit slowly, like she would any typical dildo.

After a few minutes of teasing and toying he could see the cucumber glistening with her wetness. He glanced over to one of the clocks before turning back as she aimed the cucumber at her hole and started pressing in.

He watched intently, leaning forward to watch as it split her pussy lips, giving him a view that he couldn't see normally. She was wasting no time pushing it in and pulling it out. It was just as fascinating to him watching her lips re-close once it left her body.

Just as she pushed it back in again his cell started ringing and he knew the ringtone immediately.

"Fuck!"

Bailey stopped, cucumber embedded in her pussy, and opened her eyes to look up.

"Emma."

Bailey's eyes raised as Ted got up to grab the phone, answering it.

"Hi honey!"

She may have been several feet away at the time, but there was no way that Bailey could have missed that it was her best friend on the line.

"HAPPY BIRTHDAY DADDY!" she yelled through the phone, the sound of a party favor being blown just after.

Ted held the phone far away from his ear so he wouldn't be deafened. Sure that it was safe he brought the phone back and started talking.

"Thank you hon."

He did the only thing he could do as Bailey watched--with his free hand he motioned for her to continue and she couldn't help but smile as she reached down for the cucumber and started working it in and out of her pussy more.

"Yes, Bailey came by and made me breakfast."

"No, it would have been better if you were making it Emma, but she did good otherwise."

"I've just had a lazy day. Some time by the pool, a shower, watched the Hobbit, just finished dinner a few minutes ago."

There was something almost surreal about the situation, talking to his eighteen-year-old daughter on the phone while her best friend was masturbating with a cucumber just a few feet away from him. He took his seat again to watch her while he continued to talk to Emma. She was doing most of the talking though, telling about her college orientation and the like.

It couldn't be more obvious that Ted wasn't paying as much attention to Emma as he was to Bailey. After about ten minutes he finally heard some loud noises over the phone.

"Sounds like you have some fun to get to Emma. I'll see you when you get back. Love you."

Emma telling him that she loved him, and wishing happy birthday again and Ted could finally hang up the phone. By this point Bailey was working the cucumber inside her pussy furiously, her left hand rubbing her clit as she started making more noise.

The image of juices completely covering the gourd as well as the contrast of the dark green sliding in and out of her pussy was getting Ted hard again.

"Cum for me slut, cum for me fucking that cucumber."

Bailey took in a very deep breath before crying out as she pushed the cucumber deep inside her and held it, her pussy contracting around it as her second orgasm of the night hit her. He could only be enthralled watching her cum by her own hand this time.

Her juices poured from her pussy, pooling on the chair and some even falling to the carpet--Ted suddenly realized he'd probably have to steam clean the carpet. He never really had to think about cleaning a woman's cum stain from the floor before.

It suddenly seemed funny to Ted that he had this teenage girl gyrating in orgasm just a few feet away from him and he was thinking about how he was going to clean the mess instead of just watching the show. He laughed on the inside but focused back as Bailey came down once more.

Her body was still quivering as he stood up and walked over to her, reaching down to the cucumber that was still embedded deep inside her. She gasped as he pulled it out and brought it up to his face, licking the length of the cucumber to have a taste. He let out a satisfied sigh as he tasted her sweetness, then held the cucumber up to her.

"Taste it," he commanded.

Her hand reached up to his, pulling it to her face to lick it. Her reaction to tasting herself was much more muted.

"It's interesting Ted, but I think I'd rather taste your cum to be honest."

He couldn't help but laugh as he stepped back and sat down.

"There's only one more thing Bailey. Go ahead and go get cleaned up and put on your sexiest lingerie. Call me up when you're ready."

Bailey looked at him curiously and went back for her backpack, heading upstairs. He went back to his shopping bag and pulled out the condoms and the last little surprise he bought at the store and took it upstairs.

She had closed the master bathroom and was once again taking a shower, she knew this was the end so was apparently wanting to do it right. He dimmed the lights in the master bedroom and placed the condom on the nightstand and the last surprise on the bed.

He headed back downstairs to wait. He went for the envelope and grabbed the little blue pill that had been left for him and took it. Sure he was hard now, but he wanted to make sure to do this last opportunity right.

He lost track of time as he waited before he finally heard her voice.

"I'm ready Ted."

He stood up and took a deep breath and smiled, wondering what she was wearing. He climbed the stairs and looked to find her kneeling on his bed wearing only a see-through purple babydoll that barely went down past her hips. There was a little faux fur covering her breasts and along the bottom hemline, but the effect was very sexy on the babygirl before him.

"Wow!"

She giggled at his reaction, seeing that he was already hard. She crawled toward him off the bed and stood, grabbing the box of condoms.

"We don't need this, I have a birth control implant."

He hadn't known, but he had thought. His own daughter similarly had one.

He walked up to the nightstand and instead turned on the iPod that was hooked up to the alarm. The sounds of smooth jazz filled the room as he finally turned toward Bailey and pulled her close into a kiss.

This kiss wasn't like the one that she had given him earlier, this was something much more passionate, like he hadn't given since Emma's mother died. When he finally broke it Bailey was a little stunned, speechless about his actions finally.

"Bailey, the last thing I would like is to make love to you."

"But Ted--"

He raised a finger to shush her.

"Just go with it."

He motioned behind her to the last surprise he had for her, a single red rose. She turned to him and smiled and nodded.

"Okay."

Hitting the switch to shut off the lights, leaving the room bathed only in moonlight, Ted leaned into her and kissed her once more. He knew his bed rather well as he leaned her onto it. His hands reached behind her as her head hit the pillow to untie the babydoll to remove it. Getting the teen naked once more he started kissing down the side of her cheek, down her neck to the top of her breasts.