Ted groaned as he hit the snooze button on his alarm clock. He didn’t have to go into work today, but he wasn’t particularly motivated to start the day either. He’d gone to bed forty-six years old and woke up forty-seven and felt rather blase about the whole thing. His sex life was practically non existent, his wife gone nearly ten years, and a single daughter who was getting ready to leave for college.
On any other birthday it would be Emma who’d be waking him up with breakfast in bed, something she’d done every year since she was twelve (and of course she did get better at it as time went on), however this week she was gone, at her college orientation. In many ways he wasn’t ready for her to head off to college, but he knew he had to be strong, as she wasn’t just giving up being daddy’s little princess, but she would have to give up her best friend Bailey too.
Emma and Bailey had lived next to each other their whole lives, but didn’t really become friends until the passing of Emma’s mother. Over the last ten years Ted watched as the two girls formed a bond as strong as sisters–it’d even be arranged that if something would have happened to him that Bailey’s parents would have taken care of Emma.
But now for the first time since she was eight, Emma and Bailey would be separated, each girl going to the school that was the best for them. But that meant a lonely forty-seventh birthday, and of course no more seeing his daughter’s ‘Best Friend Forever’ in skimpy summer clothing.
The doorbell rang and Ted sat up, unsure of who would be calling this early in the morning. On a typical day, only the newspaper would arrive by now, but then again this wasn’t a typical day. A sigh escaped his lips as he lumbered out of bed, dressed in boxers and a bathrobe and made his way down to the front door.
He opened it and looked out–the paper was there as expected, but also a plan manilla envelope. Looking at the envelope with curiosity he picked that up and forgot about the newspaper, shutting the door before tearing open the envelope.
Once opened, he reached inside and found three things: a stack of pictures, a letter, and a DVD. He set the pictures and the DVD down without looking and unfolded the letter to read it.
—
“Mister Rikard,
It has come to our attention that you have been without the pleasure of a woman for several years. We are also aware that it is your birthday today, so we are giving you a gift–there is of course a catch. Enclosed with this letter you will find pictures and video of a girl who lives next door named Bailey Heron in some very compromising and personally embarrassing situations.
Since shortly after she turned eighteen, we have been gathering this material. She is already being blackmailed by us into providing some of the material you’ll find on the DVD, and is aware that someday we would take her webcam blackmail and bring it into real life. Today is that day and you’ll be the instrument of that blackmail.
So until midnight tonight, when she comes over you will invite her in and then blackmail her into sex. We are aware that you are not working today and she has no plans. You are to take full advantage of the situation, enjoying her however you would want to, mostly in your bedroom in front of your computer, but other places are acceptable too.
We have already gained access to your computer, and would be disappointed to learn if you didn’t take advantages of some of the fetishes that you enjoy exploring on the internet. Also because of this, if you don’t cooperate, we will plant material on your computer indicating you as the sole blackmailer.
As stated, she knows this is coming, so feel free to show this letter to her. She should be most cooperative at that point.
Remember, we will ruin you if you don’t comply.”
—
Ted stared at the letter in disbelief for several minutes before finally setting it down. He looked over to the stack of pictures and picked it up. He only looked at the top picture and could tell it was from her house, probably from a webcam as the letter described. Bailey sitting in a chair, completely naked, pulling at her nipples. He cringed in embarrassment for the girl he’d watched grow up, but couldn’t help but notice the stirring in his boxers.
He looked to the envelope again and saw there was a fourth item inside. Once he fished it out he groaned again, a 100mg Viagra pill wrapped in plastic. He took several deep breaths then sat down, needing time to think, to try and figure things out.
Time passed, perhaps an hour as he tried to reason through the situation in his mind–the DVD and the pictures drawing his glances every once in a while. He was tempted, how could he not be by this girl twenty-nine years younger. Before he knew it, the doorbell rang again and he instantly knew it was Bailey.
He put the manilla envelope over the pile of its contents–save for the letter, and went to the door. As soon as he opened it Bailey yelled out, “Happy Birthday Mister Rikard.”
Ted couldn’t help but grimace a little at the girl, but he thought for a moment about sending her away before finally saying, “Come in Bailey, and thank you.”
Bailey didn’t hesitate at all as she entered the house she’d spent quite a bit of her youth in. Ted couldn’t help checking her out, in her shorts and tank top, with a bikini as underwear. Bailey was a pale, freckled redhead who generally wore a lot of sun screen in the summer. As soon as he closed the door she rounded on him with a hug and a smile. “Emma wanted me to give you that hug since she couldn’t, and wanted me to make you breakfast.”
He cringed a little and looked down at her as she broke the hug. “That’s great Bailey, but before you do that, we need to talk.”
Bailey couldn’t help but notice that he sounded a little odd, and with a look of concern on her face she made her way over to the couch. “Is everything alright Mister Rikard?”
She knew she could call him Ted, but her parents had raised her to be respectful of her elders so she’d always addressed him so formally.
“Yeah. I mean, no, not really.” He couldn’t find the words so he did the only thing that made sense to him. He just handed her the letter.
Ted sat down and watched nervously as the girl read the letter. It seemed to take her a long time, as though she was reading it several times just to make sure. Finally Bailey looked up and said, “I was afraid this would happen.”
He was surprised. He doubted that the letter was genuine (even though the pictures were obviously). With a bit of concern he asked, “So what’s going on Bailey?”
The teen let out a long sigh. “Well, as you know for my eighteenth birthday I got a new laptop. Well, it wasn’t brand new, my parents couldn’t afford one this year. Apparently where ever they got it, someone had already hacked into it. It started out simple, apparently they got pictures of me in my room changing and stuff like that, then one time they got a video from afar of me on my bed masturbating.
“From there the blackmail really started. They made me perform for a video once a week, and every night about ten minutes before I went to bed I had to pose for a photo in whatever way they wanted. I’m sure the pictures come from those.”
She looked hesitant for a moment, wondering where they might be before Ted spoke up. “I only saw the top one Bailey. I haven’t looked through them or the DVD either.”
The expression on Bailey’s face was one of forgiveness. “Thank you Ted for being considerate, but I suppose it won’t matter since you’re going to get to see and feel a lot more of me than the photos and videos would provide.”
Ted was stunned into silence for a moment–‘did she really just say that?’ he wondered to himself. The fact that she actually used his first name was completely missed by him. “Are you saying you’re going to go through with it?”
She stared at her best friend’s father with an incredulous look on her face–he was about to stammer in response before she finally said, “Go through with it? I don’t see what choice we have? They’ve threatened to ruin you if you don’t, and who knows what they’ll do to me if I refuse.”
Bailey stood up and looked to the front door. “I’ll be back in ten minutes Ted,” she said, heading to the door and exiting the house without waiting for a response.
To say the wait to see if Bailey was returning, or if possibly cops would be knocking on his door was rather agonizing for Ted. On the one hand, he’d watched Bailey grow up from a kid into a very cute young woman. And sure while he’d try to catch glimpses of her body in revealing clothes or swimwear when he could, he never actually thought about fucking the girl.
His front door opened and Bailey returned, now with a backpack in hand she quickly set on the couch. She returned to the door and closed it, locking the deadbolt as well. She looked at Ted and took a deep breath. “So I brought my laptop over–so that way if the blackmailers are paying attention they can see the first bit of things to know we’re both cooperating.”
She went back to the backpack and reached in, pulling the laptop out and setting it up on the coffee table. The computer sprang back to life as she opened the lid. Ted wasn’t sure what instant messaging program it was she opened, but saw her quickly type “We’re complying” to someone and hit the send button.
“So how do you want to go about this Ted?” Bailey said. “I know these people, they’ll want me naked immediately, but we can either get right to the sex after, or I can still fulfil my promise to Emma and cook you breakfast.”
Ted was still stunned at the turn of events. He looked away from the girl and mumbled, “Breakfast.”
He didn’t look back up until Bailey reached out to his face and brought it to look at her own anger-filled one. “Look Ted, we don’t really have a choice here. You think I like that they made you the other target of this scheme of theirs? Not just no, but hell no. Emma’s a sister to me, and you’re like a second father, and now I’m being forced to fuck you for the rest of the day. This is going to change things between us, and probably make them awkward for a while Ted. But I don’t want you implicated in a blackmail scheme, and the last thing I want is all the pictures and video they have getting sent to people I know and care about.”
“I know you don’t Bailey,” was all Ted could reply.
“I just want one favor from you Ted,” Bailey said, her expression changing from the angry, ranting face to one a bit more worried and unsure.
“What is it Bailey,” he asked tepidly, the change in her expression catching him off guard.
She inhaled a deep breath and held it for a moment before slowly exhaling, a slight waft of the peach lipgloss she was wearing reaching my nose. “From now until I can leave as instructed, please don’t see me as Bailey, Emma’s best friend and girl you’ve watched growing up. For the rest of the day I’m just some dumb whore who you’ve been given to fuck however you want. I know these people, and if you try to take it easy on me because you care, we could both be screwed. So I’m just some girl whose only job is to please you. Can you please do that for me Ted, just forget I’m Bailey and do this right so we won’t get in trouble?”
Bailey’s voice started to crack at the end–looking more closely Ted could see that she had tears welling up in her eyes. He hated the situation, but he understood what she was asking–to detach her body from the girl he knows. He knew there could be only one response.
“For you Bailey, I will.”
Bailey stepped back, a faint hint of a smile on her face–possibly the last he’d see for a while. She looked right at Ted and said, “So sir, would you like me to strip, or do you have some other idea for getting me naked?”
Ted closed his eyes. He promised Bailey that he would ignore that she was his daughter’s BFF, and that was what he was going to do. He knew she was scared of these blackmailers, so he was going to uphold his end of the deal. After all, he’d hardly gotten any over the last ten years, might as well try to enjoy this one shot at a day filled with carnal pleasure.
“Kick off your flip-flops and come over here and kneel before me, hands over your head.”
For just the slightest second he saw Bailey’s face betray a sense of surprise–then perhaps one final smile that he was indeed doing as promised before he saw her kick off her flip-flops and move closer to him. Bailey did as ordered, kneeling before him and putting her hands over her head.
Ted’s hands reached under the tanktop she wore and just felt her belly for a moment. In most ways Bailey was your average teenage girl–she was skinny, but without tone or definition. He knew from seeing her in a bikini before that she had just the right amount of babyfat left for his taste and now he was getting to feel it. His hands squeezed a little bit, feeling how her muscles were just barely below the surface, but enjoying the softness of her skin provided by her lack of well-defined abs.
He closed his eyes for a moment as he ran his hands over the soft flesh before finally dragging his hands upward. He enjoyed feeling her sides, only brought back to reality by a slight giggle from her–apparently she was quite ticklish. He opened his eyes to watch as he adjusted his hands to grab the tanktop and pull it up over her head and off her body.
Bailey’s bikini top was one he’d seen her wear before–black with strings tying behind her back and her neck. Ted had to debate for a moment how he wanted to reveal her breasts. Finally his hands reached out toward her side and slid underneath the fabric of the bikini top, gripping her firm breasts from the side and pulling them out of the top.
Gazing them finished making him hard. He’d always seen her breasts in bikini tops and got quite an eyeful of skin, but having them completely exposed, seeing how pale pink and tiny her nipples were as opposed to only hints. He kept his hands gripping them, feeling how they perfectly fit his hands. Ted couldn’t help himself as his thumbs brushed over her nipples, causing her to gasp.
“I take it you like having your nipples played with Bai…” He stopped, remembering the deal. “Slut?” he changed the word to.
She nodded to him and he grinned. “Excellent. Reach back and untie your top, then put your hands behind your head.”
Ted continued to squeeze her young breasts and tease her nipples with his thumbs while Bailey worked to remove her top. He still hated that he was being forced into this, but he was starting to see the perks of just rolling with it and doing as he’d been told.
When she was done untying the bikini top it fell onto the ground and she placed her hands behind her head, pushing her firm and perky breasts out. Ted removed his hands at that point to just gaze at the fleshy orbs in all their glory, a tad surprised at how far her nipples were sticking out now that they were hard.
He knew he could just stare at her tits for hours, but there was plenty more to unwrap and experience. “Stand up slut,” he barked, falling a bit more naturally into the dominant role the more he felt and saw the eighteen-year-old.
Bailey stood up, her face betraying no reaction–she was obviously not considering this to be as if she were a lover, but seemed to be taking it solely as something that needed to be done. He reached up, unbuttoning and unzipping her shorts and tugging them down her legs, revealing the matching black bikini bottoms he had expected to see. The girl naturally stepped out of the shorts once they were on the ground and kicked them aside.
Giving into the temptation became much easier for him now that only a little bit of fabric stood between him and seeing this soon-to-be college girl completely naked. He looked at the string ties on the side of her bikini and knew exactly how he wanted to do it.
“Alright slut, I want you to turn around and bend over, hands on the coffee table and spread your legs.”
To her credit she complied without batting an eyelash, turning around and spreading her legs to either side of his before bending over and putting her hands on the coffee table–her ass in his face. Ted wasted no time in reaching out and untying the right string–the bikini bottoms falling open to reveal most of her right buttcheek. Even though he knew she was pale, he was still surprised by the difference in skin color from her legs to her ass, and suddenly found it a bit weird he didn’t see that with her tits.
He wasted no time in undoing the other tie and letting the bikini bottoms fall to the floor. Ted’s face lit up like a kid on Christmas morning as Bailey’s most intimate of intimates were on display a mere foot from his face. Sure, he’d seen plenty of teenage pussy lately watching porn, but to have it right before his eyes was something he hadn’t experienced since he was a teenager himself.
Almost instinctively his hands reached up to grab her ass firmly, spreading her cheeks so that nothing was hidden from him. In Ted’s mind he cursed himself for not having a photographic memory as he studied every detail he could. He couldn’t help but smile as he realized he missed the very subtle transition between normal skin and her outer labia–he would have missed it entirely if her inner lips weren’t so prominent. His eyes lingered over every wrinkle and fold of the soft pink flesh as though he were looking for a flaw–the closest thing he found was the realization that the way her pussy naturally splayed open as he held her separated meant that Bailey was no virgin.
Ted really couldn’t help himself as his right hand released it’s grip on her right cheek and his fingers drifted over–his curiosity got the best of him and he wanted to know if this was a turn-on for her as much as it was for him. If Ted thought his cock couldn’t get any harder he discovered that he was wrong as his probing of her velvety opening by his index finger yielded that Bailey certainly was wet.
It took a lot of willpower for him to not just take her then and there, but his hand reached back up to spread her once more as he leaned forward, burying his nose against her pussy and inhaling her scent. Ted knew if he dropped dead this instant he’d die the happiest man in the world, but there was so much more to experience even in just this one day.
He finally leaned back and let go of her. Trying to push the fact out that this girl was like a second daughter he said, “Have a seat slut.”
Bailey did as she was told, sitting down on the coffee table instead of a chair–it was the only way she could properly face him.
“I’m going to ask you some questions and I want you to answer honestly,” he told her. “Are you a virgin?”
She shook her head, “No sir.”
“Have you ever given head?”
“Several times sir.”
“What about received it?”
“No sir, never.”
He was a little surprised, but he continued on. “What’s the oldest guy you’ve been with?”
“Twenty.”
“Have you ever had anal sex?”
This was Bailey’s first hesitation on a question, but the girl just took a deep breath and said, “No sir.”
A rather large grin overtook Ted’s face now–anal sex videos were one of those things that the blackmailers were probably talking about with his proclivities. His former wife was a rather vanilla woman, something he wouldn’t have changed for anything, but in his older age he definitely found a desire to explore more taboo ideas.
“I think it’s time for breakfast,” he suddenly blurted out again.
The teenager stood up and nodded, looking at the laptop for a moment before making her way to the kitchen. “Why don’t you sit at the table and I’ll get to work,” she suggested.
Ted did so, angling himself so he could watch her work. Cooking was nothing he found particularly glamorous, though it had a slightly different look to it when it was a naked girl doing it. He didn’t pay attention to what she was cooking, or even how long it was taking her to do so–there was just something erotic about being served in this intimate way.
He was only snapped out of his trance once he realized that she was bringing breakfast to him. She set the table only for him and had a plate full of sausage, eggs, pancakes and toast–all done just the way he liked. When he realized she didn’t set a plate for herself, she simply waved him off. “I already ate sir.”
The moment of truth came for Ted–he knew he couldn’t just simply eat and have her sitting or standing naked before him, he might as well get something out of it. Looking at the girl and debating, he decided on his course of action.
“Alright slut, I want you to get down on your knees and give my balls a tongue bath. Once I’m done with breakfast we’ll test how well you can suck cock.”
With that he knew he was committed, his relationship with his daughter’s best friend could have survived just the way it was until this point, but the line was finally crossed. For her part, Bailey said nothing as she knelt down before him. He stood momentarily, allowing her to pull his boxers off for better access. He knew he’d been rock hard for a while but he’d never seen his cock look so angry and purple with lust. Precum was already oozing from the tip–Ted couldn’t remember the last time that had happened by itself. What he found most surprising was that Bailey didn’t seem phased by seeing his cock at all.
There was no smile on the girl’s face as she nuzzled in between his legs so her tongue could get at his balls–that was the only thing Ted found disappointing about the whole situation; he wished that she had been doing this because she wanted to, not because some creep was forcing them into it. Ted violently shook his head–what was he thinking? He didn’t really want Bailey doing this at all. Or did he? Was Ted actually letting his lust take over unabated?
A resounding yes was the answer in Ted’s brain as Bailey’s wet tongue made it’s first contact with his balls. He had completely missed that she managed to move his cock out of the way so she wouldn’t brush against it as she positioned herself. He was probably missing a lot of things as he just concentrated on the feeling as the tip of her tongue explored every ridge and every wrinkle of his sac.
Ted spent about two minutes with his eyes closed just enjoying the feeling before remembering that he had a breakfast in front of him to eat. A wide grin covered his face the entire time he ate his meal–the girl dutifully did what she was asked and didn’t stop for one second. Of course there is only so long a guy having a girl almost nearly thirty years younger licking his balls can go before he wants something more. Setting his fork down he finally looked down at the girl and said, “It’s time.”
“Shall I do it here, or would you like someplace more comfortable?”
He started shifting himself in the chair, aiming to get up when he felt it–a tightness he hadn’t felt since he was a teenager himself. Having her here, naked, tonguing his balls had built up an anticipation he hadn’t experienced in decades–Ted found himself hurting from blueballs. He could only muster, “here.”
Bailey nodded and licked her lips as she looked over his shaft. Any last chance that this was just a wonderful dream evaporated as her right hand grabbed the base of his cock to steady it. Her lips parted as she leaned forward and the head started to disappear into her teenage mouth.
He wasn’t really sure how much head she had given, but he was surprised when she got the whole head inside without actually touching it. Her lips finally made contact with the shaft just past the head–the girl pausing to look up to see Ted staring rather intently at her. The teen let go of his shaft, closed her eyes and leaned in, taking more of his rock hard cock into her warm, wet mouth.
Now Ted had never purposefully imagined what it would look like if Bailey were to suck his cock–she was too much like family for that. There were times, however, that in a dream the image came across, and her head in his lap, her perfectly-pink-lip-gloss-covered lips trailing down his shaft looked even better than his dreams ever depicted it.
There was a slight problem though that Ted quickly realized–he’d been so hard for so long that he was bursting to cum. He dug down deep, trying with all his resistance to just enjoy this feeling for what it was, to hold out as long as he could–but when Bailey flicked her tongue across the bottom of his head as she started to withdraw Ted lost any remaining semblance of control and shot the strongest wad of cum into the teen’s throat that he had in years.
Bailey was caught slightly off guard by how quickly she had made him cum, but she handled it like a champ, starting to swallow on the second shot, playing catchup as her mouth still worked the shaft. Ted’s hand instinctively reached for the bottom of the chair and he held on, just riding the most powerful orgasm he’d had in decades out.
He didn’t keep track of how many shots of cum he had just fed to Bailey, he just knew the ache of both his balls and of a cock that was ready to jump off his body had subsided. Even as he grew soft Bailey kept him just barely inside her mouth, her tongue sliding along the head to gather any remaining cum that hadn’t shot out naturally. Finally after a long minute of Ted’s breathing heavily, she removed herself from him and stood up.
Still catching his breath, Ted watched as Bailey went to the fridge and started searching through it for something. He knew he shouldn’t have been surprised when she came back to the table with a can of the energy drink that Emma and her drank a little too regularly–neither girl needed the extra energy in reality. However, he did betray a look of surprise when after opening it she handed it to him.
“I figure you’re not done yet. You have got to keep your energy up.”
Ted took the drink from her and glanced at it before finally taking a sip. Reflexively his face cringed as the vile drink hit his tongue. “I don’t see how you girls drink this stuff.”
“You’ll find we’re not picky about what we’ll put in our stomachs Ted,” she said with a wicked grin on her race.
His eyes still ran up and down Bailey’s naked form as she stood before him. She was right after all–it was rather weird to think about it, that odd little realization that his cum was in her stomach, slowly being digested by her. His cum, in the stomach of an eighteen-year-old. The euphoric high he was on was enough to quash the taste of the energy drink as he started gulping it down.
Bailey had started looking around, her eyes darting to the backyard. “You know, it’s about the perfect time of day to go out and get a little bit of sun.”
“Good idea, you’re right, I need a little time to recover anyway.” He felt a little pang of guilt. “Sorry about um…”
Bailey started laughing–she knew instantly he was about to apologize for cumming so fast. “I take it as a compliment. Besides, I’m sure once we get you rested you’ll last much longer next time.”
With a bit of relief he finally finished off the energy drink and stood up. “To the pool then.”
Bailey nodded and went over to her backpack and fished out a tube of sunscreen. With a smile on her face she confidently walked out to the pool area.
Ted and Emma’s backyard had high enough fences, and enough separation from the neighbors that the only way one could see into it would be via intentionally trying to spy. Bailey had spent enough time swimming in the pool and in the yard in general that she had no worry about privacy. Ted followed her out, watching the swaying of her hips and the wiggle of her ass as she walked. As mad as he wanted to be that he was being blackmailed into doing this to someone who was practically a daughter, a large part of him wanted to thank the blackmailers for the experience.
Once out on the patio she waited for him to sit in one of the lounge chairs. He still had his bathrobe on which alleviated the need for a towel. Looking up he wondered what the girl would do next.
“I take it you’ll want sunscreen too?” she asked rather casually. “Would you like to put it on or would you like me to?”
“You can apply it to me Ba–slut,” he told her, correcting himself.
“Any particular way?”
“Something sexy, erotic.”
Bailey nodded as she stood next to him, pursing her lips as she tried to decide how she could and should fulfil the request. The surprise Ted had that she was still doing this even without the webcam watching subsided as he thought about her experiences with the blackmailers–she had probably done enough that if they felt she didn’t do her side of the bargain they’d make her pay. He knew that if the blackmailers had been monitoring what he was watching online, then she still had a few tough challenges ahead of her.
A giant smile appeared on Bailey’s face once more as she leaned down, crawling onto the deck chair with Ted, straddling him once more. She sat naked straddling his stomach as she opened the sunscreen tube. Raising the bottle to her face, she turned it upside down and squeezed, covering her tits with the white cream. For just a moment he was confused as she was letting the sunblock pile up instead of spreading it around.
The teen set the tube on his stomach and leaned forward, her plan becoming obvious as she maneuvered her tits to his face. Very carefully she rubbed her breasts against him, trying to keep the lotion away from his very wide eyes. It certainly was erotic in Ted’s mind, the girl applying the sunscreen with her soft, supple breasts. The only problem was that the method wasn’t practical for long.
After only a minute of rubbing her breasts all over his face she retreated, bringing her hands up to finish spreading the sunscreen over his face. As she leaned back further she scooped the rest off her breasts and started applying it to his neck. The next several minutes were a new experience for Ted as she rubbed the high SPF lotion into his body. Once she got to where she was sitting she stood up and turned around, straddling him a little higher on his chest as she continued rubbing down his body–giving Ted an eyeful of her pussy and the tiny little rosebud of her anus.
Even though the girl was rubbing her hands all over his legs, he only had eyes for the sight in front of him. When she started to crawl off he was a bit disappointed until she moved into a deck chair of her own.
“Would you like me to lotion up myself or would you like the honors.”
Ted jumped out of the chair with the speed of a much younger man–there was no way he could turn down the opportunity to rubdown a teenage girl.
For her part, she laughed at his exuberance. “Front first, I’ll turn over and you can do the back later.”
He wasted no time in bending over the girl, rubbing some cream on her face–that wasn’t his real focus though. With her fair skin it was essential that he apply the lotion properly, and yes he made sure to do that. Finally though he reached her breasts and couldn’t help but grin. He squirted out a large dollop of sunscreen on each of her nipples; she shivered slightly as even in the heat of the day the lotion had a coolness to it.
His hands reached down to cup her breasts, using his thumbs to spread the protective cream over her nipples first. To no surprise he felt the pink nubs stiffen. Finally Ted had to abandon all pretense and he moved his palms to start rubbing the lotion all over the incredibly soft fleshy orbs. He enjoyed every moment feeling her nipples brush against his hands as he squeezed and toyed with the flesh, but he knew it was time to move on.
As he worked more of the sunscreen into her stomach she had to grab the chair and hold her breath in order to keep from laughing–Ted made a mental note that Bailey was ticklish, not that he’d ever get to exploit it after tonight. He kept on working his way down her body, avoiding her mound for a moment, instead focusing on her inner thigh and her legs. Once more Ted had fun as he got to rub her pussy–even though it was all about protecting her. He didn’t even really concentrate on applying coverage properly, he just liked rubbing his hands across one of the more intimate areas of her body.
Ted gave up after about five minutes, looking to Bailey a little sheepishly.
“Don’t worry Ted, I’ve never put sunscreen there myself, so it’s okay. Go ahead and relax, I’ll need more help in thirty minutes or so.”
Doing as he was told, he sat back down to watch and to wait. Eventually he closed his eyes for a power nap, figuring that any energy he could recoup would be more than worth it in the end. Instantly he woke up, unaware of how long he was out, but the shock through his system as her tongue once more licked the head of his cock made him more awake than he had been all morning.
“I’m ready for the backside now.”
Once more he was happy to honor her request as she laid down naked on her chair. As he got back to rubbing the lotion into her skin he cursed silently under his breath–a sudden wish for a jar of honey dust overcame him.
“What’s wrong?” Bailey had evidently heard him.
“Nothing, nothing at all.”
Like her front half he decided to save the best for last, working her back, arms, and legs first. His path took him back to her perfect little ass. As he started rubbing the lotion onto it he felt the contrast between the soft skin and the firm muscles underneath. Soon he was trailing the greasy sunblock between her cheeks.
Suddenly he stopped, pulling his hands back. Ted looked at his right hand, noticing how greasy it was from the sunscreen. His hands returned to her ass as his left hand spread her left cheek, and his right hand moved along the crevasse of her ass. When his index finger reached the pucker of her asshole Ted froze for a second–before finally applying pressure, forcing his finger to enter her ass.
Bailey let out a noticeable gasp.
Ted, concerned, questioned her. “You Okay??”
She hesitated for a moment. “Yeah, sorry, you just surprised me. I’ve never had anything in my butt before.”
“Okay.”
Ted couldn’t help but smile–the way she used butt instead of ass. His finger pressed further, sawing into a hole far tighter than he could ever imagine. He went slow, closing his eyes and just embracing the feeling as Bailey’s most forbidden hole wrapped tightly around his finger. After pulling out he pushed back in, slowly starting to saw his finger in and out of her ass. He listened as her breathing changed every time he pulled out and every time he sunk back in.
With his eyes closed he started picturing the rest of the day–he knew what the blackmailers would expect, and he knew he might as well get some enjoyment out of it. Finally he pulled his finger completely from her ass and got up to sit back down in his chair. As he got comfortable again, he noticed that his erection had completely returned–sure, it was flirting with growing this entire time, but finger-fucking her ass got him ready.
It was another half-hour before Bailey started to move again.
“I’m going to go for a swim, want to join me?”
Ted thought about it and shook his head. “Nah, I’ll just watch for now. But after, we’ll need to make sure to take a shower to clean off the chlorine.”
Bailey looked at him with a curious gaze, but just smiled and nodded before jumping into the pool. Ted watched her swim–not unlike how he’d watched her swim in this pool before, but never with her naked and him with a raging hard-on. He didn’t pay attention to how long she swam, but he could only smile as she came to the edge of the pool and pushed herself up over the lip and climbed out.
“Time to clean up,” she declared proudly.
Like when it was time to apply sunscreen, Ted quickly extricated himself from the chair. He followed Bailey into the house, again watching her walk. This was going to be unfamiliar territory for the girl–as far as he knew, she had never been in his bedroom, nor his bathroom.
“Should we grab the laptop?” he asked curiously.
“Would the camera pick up in the bathroom?”
“If we keep the door open and the fans on it should, yes.”
Bailey nodded and he moved back to the kitchen to grab the laptop. He followed her upstairs as she went to his room. The girl glanced around before seeing the entrance to his master bathroom. As she stepped in, Ted could see the look of surprise on his face. He never talked about it, but he was well enough off–he made sure that the house and his master bath were comfortable.
The large walk in shower with clear glass windows and multiple shower heads aimed for the body, with a very nice removable massage shower head up top. As Bailey was looking at it, Ted set the laptop down to point at the shower before heading over to the control panel next to the shower. Hitting the button, he set the temperature to a comfortable one hundred five degrees. She jumped as the jets suddenly sprang to life and the fans turned on to help remove any steam buildup.
“Wow, this is a very nice shower Ted.”
He shed his bathrobe and motioned for the teen to step in. As she stepped into the water she let out a rather audible hum.
“I wish I had something like this.”
The grin that hadn’t left his face grew just a little wider as he stepped into the shower behind her. Grabbing a bar of the soap he started to rub it along her back. She raised her shoulders, trying to provide him some easier access, and with his free hand he guided her, turning her to face the spraying jets.
“Mhmm, that does feel good,” she cooed.
While none of the streams of water were hitting her erogenous zones, it was close enough to illicit a response from her. He kept on soaping further and further down her back until he reached her ass.
“Alright slut, spread your legs and lean forward.”
She didn’t hesitate, doing as he asked her–sticking her ass out in the process. As the water from the primary shower head washed the soap down her back he brought the bar to her ass and started rubbing it up and down her crack. As the bar worked against her recently finger-fucked ass, she took a deep breath.
“Please be gentle, this will be a first for me.”
If there was any point in the process that Ted was going to feel guilty about the situation, this had to be it. As it was, that tight little hole, just inches from his cock as he lubed it up with the bar of soap was just too much for him–his lust was in control and he was about to get something he’d been dreaming about for a long while.
Ted moved behind Bailey and set the soap bar back on the tray. He reached down to her hips and his hands slipped as he tried to grab on. He let out a little laugh as he grabbed a little more firmly. He moved closer, placing his cockhead against her soaped up asshole. Looking down at the teen, he pushed forward at the same time he pulled on her hips, slipping into her eighteen-year-old ass.
Bailey let out a cry as he held the head of his cock in her ass. She started to breathe deeply, yet rapidly, using her breathing to try and reduce the pain. Sympathy was lost on Ted for the time being–he finally had done what she asked. He didn’t see the girl whose rectum he was invading as a daughter-figure, she was just some girl he had to fuck.
His newfound lust taking control, he pushed further into the teen’s ass as she braced herself against the wall. He was pulling her onto his cock as well, but for a moment he thought she might be helping. Pulling out of her ass was followed by pushing in further. He only had one goal–to bury his cock to the hilt in the ass that was tighter than anything he had previously experienced.
Stamina was finally on Ted’s side. He was so close that finally he paused with just his head left inside her ass and with all his strength he pushed forward with his hips while pulling her back onto his cock. Her cry was much louder as he buried himself completely in her most private of spots. It was heaven to him, but the cry from her snapped him back to reality.
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.
His left hand drifted to her pussy as his lips kissed down her cleavage before teasing her nipples. The soft gentle kisses and the light rubbing of her pussy were departure from earlier. Ted wasn’t too surprised that she was still wet from her recent orgasm as he moved into position. Looking into her eyes he smiled. “I know you were made to do this, but if it had to be anyone, I’m glad I was gifted with this wonderful day.”
She beamed brightly at him. “I’m glad it was you too Ted.”
He leaned down kissing her again as he lined up his hard cock at her pussy and pushed in. The wetness and the warmth of her love tunnel was a wonderful experience for him as he started thrusting in and out of her.
Ted wasn’t kidding, he truly wanted to make love to Bailey and did so, slowly thrusting in and out, enjoying his time inside her. He spent the entire time looking into her eyes, or kissing her. One hand reached up to her breast, the other down to her pussy–she decided that she was going to at least honor this by enjoying it as much as he was.
Neither of them paid attention to how much time had passed, how many songs had played, they genuinely enjoyed their time together as one. When it was finally time Ted held out as long as he could–it wasn’t quite simultaneous, but as he started to cum she was able to push herself over the edge. Ted waited until both of them were done before he pulled out and laid beside her.
“Bailey?”
“Yes Ted?”
“Please stay cuddling with me. I know you can leave at midnight, and I expect you to. But again, thank you.”
She didn’t say anything to him, but she nuzzled alongside him. Her arm across his torso they both fell asleep.
*****
Ted woke up the next morning, quickly looking to the spot last occupied by Bailey. To no surprise but much disappointment he found his bed as empty as it normally was. As he crawled out of bed he had to wonder if it had indeed happened, or if he just dreamt the whole thing. Before he could really think about it he smelled food cooking. Quickly reaching into a drawer he put on a pair of boxers and ran out of his room and down the stairs faster than he had in years.
Arriving in the kitchen he saw Bailey once again cooking breakfast, only this time she was at least wearing a little clothing–one of his button up shirts to be exact. Bailey turned and smiled to a rather dumbstruck Ted.
“Don’t tell me they’re making you continue?” he asked the girl he spent the prior day fucking six-ways-from-Sunday.
“Not quite,” Bailey said still smiling, “sit, we have to talk.”
He was used to taking orders from his own daughter, but it had been many years since he took orders from someone he slept with. Ted’s curiosity got the best of him and he sat down at the table Bailey had already adorned with food.
Bailey brought the last of the breakfast over, sausages, and put some on both plates before sitting down herself.
“So,” Ted said, unsure of what exactly was going on.
Bailey put a finger up to her lips to silence him. “I’ve got a confession.”
Ted maintained his dumbstruck look, but said nothing.
The teenager took several deep breaths before saying, “Ted, you were set up. There is no blackmailer.”
His expression didn’t change. Ted was very much confused and unsure of what she meant. “What do you mean there’s no blackmailer? What about the pictures? What about the video?”
Bailey blushed as she looked right at him. “Well, that’s the thing. We made it up. We took the video and the pictures?”
Ted looked a little more concerned. “We?” he asked.
“Emma and me. We set the whole thing up,” she replied.
“Emma and you?” Ted was slowly trying to comprehend it all–he took a sip of coffee to try and wake up.
“That’s right.”
“Explain.”
“Well,” Bailey said before a quick sip of juice, “it goes like this. Emma and I have been watching you, noticing that you’ve seemed increasingly lonely. And we’ve known you weren’t getting any.”
Ted was about to object but Bailey just held her hand up.
“So we devised a plan to get you some action. Emma had seen your browsing history on your computer and saw you went for college girls, and of course some of the other things we explored yesterday. We didn’t want to hook you up with some skank so I volunteered. We’ve seen how you’ve glanced at me at times over the years.”
It was Ted’s turn to blush and attempt to object, but Bailey was on point again in holding her hand up.
“So we decided that you would fuck me, however you wanted. But we had to figure out how to do it, so we decided to concoct the blackmail scheme. My webcam took pictures of me, and some from my phone with Emma’s help. A few videos, based off of things that you’d looked up online,” she motioned to the dvd that he still hadn’t watched, “and figured we could trick you into it. It was the only way to convince you to do it, because we both know you were way to decent to ever do so even if you wanted to.”
Ted nodded at the last bit as he sat there stunned listening to the teen’s tale.
“So here we are. Your birthday present was set in motion. We made up the letter, put in the pictures and videos and just had to wait, hoping we made it threatening enough that you’d go through with it.”
Bailey closed her mouth and looked resolutely at Ted, waiting to see what he had to say.
He had to take another sip of coffee first, digesting what she had just told him. Ted nodded a few times before talking. “Well, you were right that I wouldn’t have slept with you if you had just offered yourself to me. I know part of me should be mad that you tricked me into having sex with you.”
He paused for a moment, looking his daughter’s best friend over in a new light.
“So you knew everything that we were going to do?”
“Yes”
“You knew I’d want to spank you.”
“Yup.”
“And have you masturbate with the cucumber.”
“I suspected as much.”
“Even fucking your ass?”
She smiled wickedly at him.
“Oh yes Ted, I knew about that. I had to think about it, knowing that would come up but honestly, if I was going to lose my anal cherry, I wasn’t kidding when I said I’d rather it be you than some random guy. At least with you it was something special, that you treated it like the treasure it was.”
Ted was floored. He just stared at the teen for a long while before speaking.
“Okay, I know yesterday must not have been the easiest thing for you, and you’ve definitely awoken feelings I wasn’t sure were still there. But I have to ask, what does this mean for the future? Where do we go from here, you’re not exactly just my daughter’s best friend anymore, are you?”
Bailey smiled very warmly to him once more.
“Well, that depends on you. You’ve known my body more deeply than any other man has, but of course we could never be together in any serious way.”
Ted nodded a bit at this point–she was right of course.
“However,” she continued, interrupting his thoughts, “that doesn’t mean that until I go away for college we can’t have a little fun. Emma’s okay with it, she just doesn’t want to hear about it, you being her dad and all. But if you want, we can certainly continue exploring each other like we did yesterday.”
Ted knew he should say no, he really did, but this girl offering herself to him now was very hard to resist.
“Do you have anything in mind?”
Bailey laughed and stood up from her seat, unbuttoning the shirt and sliding it off, once again standing naked in his kitchen. The teen moved around the table and sat in his lap, putting her left arm around him.
Her soft breasts in his face, and a sly smile on her face as she wiggled in his lap, she cooed, “I definitely think you need more time in my mouth. Let’s get you fed and you can be the first guy to sixty-nine with me. Only if you want to of course.”