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.
Sam 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. Sam 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 Sam 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 Sam, 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 Sam’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 Sam 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 Sam 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.”
Sam 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 Sam 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–Sam 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 Sam 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.
Sam gave up after about five minutes, looking to Bailey a little sheepishly.
“Don’t worry Sam, 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. Sam 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 Sam froze for a second–before finally applying pressure, forcing his finger to enter her ass.
Bailey let out a noticeable gasp.
Sam, 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.”
Sam 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?”
Sam 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. Sam 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, Sam 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, Sam 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, Sam 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 Sam.”
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 Sam 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.
Sam 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 Sam 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 Sam’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 Sam. 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 Sam’s thrusting.
“Squeeze my tits,” Bailey suddenly yelled out.
Sam 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.
Sam 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.
Sam 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 Sam 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.
Sam 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.”
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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 Sam sitting on the couch wearing the bathrobe. Remaining naked, she sat down in front of him on the coffee table once more. “Everything fine?”
Sam 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 kind of a 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 Sam, 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 Sam, 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 Sam.
“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 Sam, 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. “Sam, 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 Sam.”
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.
Sam 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 Sam 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 Sam came back down Bailey was already gone.
The hour passed quickly. Sam 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, Sam 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.”
Sam 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. Sam 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. Sam 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. Sam’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 Sam 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.
Sam 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 Sam 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 Sam 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 Sam 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–Sam 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 Sam 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 Sam, 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 Sam.”
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 Sam–”
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, Sam 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.
Sam 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 Sam.
“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. Sam’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,” Sam 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, “Sam, you were set up. There is no blackmailer.”
His expression didn’t change. Sam 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?”
Sam looked a little more concerned. “We?” he asked.
“Emma and me. We set the whole thing up,” she replied.
“Emma and you?” Sam 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.”
Sam 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 Sam’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.”
Sam 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 Sam, waiting to see what he had to say.
He had to take another sip of coffee first, digesting what she had just told him. Sam 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 Sam, 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.”
Sam 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.”
Sam 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.”
Sam 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 69 with me. Only if you want to of course.”
THE END
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Story 19
The Bride
A Non-consent/reluctance story of a Blackmailed Bride.
Chapter 1
A Week Away
“Brenda, please,” Tan pleaded, “we’re almost married. Can’t we have sex now, sweetheart?”
We had been kissing on the bed for over thirty minutes and I was definitely hot and bothered, but Tan had wanted to go too far. I got up and fixed my hair, make-up and clothes, all of which had suffered in the process. Tan and I were engaged. We dated for a year, and then got engaged about six months ago. So far, I had managed to put him off, wanting to be pure for my wedding night. I admit it was getting harder and harder to resist sex with him. I was so easily aroused when we started kissing and petting one another. I let him touch my bare breasts and even my vagina a couple times, though as soon as he tried to put his fingers in me, I shut him down. It was too much like sex, but I loved him so much and wanted my first time with him to be extra special.
Tan was twenty-six and so, so handsome. Tall, a couple inches over six feet, lean and athletic, but muscular as well. All of my girlfriends drooled when they saw him, and I could not resent it, because I liked to watch him too. The way he walked, like a panther, his muscles gliding under his skin, commanding a room when he walked in, people noticing him. You might think he was rich or came from wealth, used to people waiting on him hand and foot, but though he was well to do, he wasn’t rich and didn’t expect anyone to wait on him, even me.
His hair was dark and he had dark brown eyes with lashes so long, girls envied him. He had a ready smile and shared it often, dazzling us with his wit and charm. I couldn’t believe he had fallen for me. I was two years younger than him, fairly tall, five foot, nine in my stocking feet. I had what I considered to be ugly, mousy brown hair, a rather plain, oval face, a too wide mouth and turned up nose with freckles I hated with a passion. Oh, I guess my boobs and ass were all right in the scheme of things. Thirty-six with a C cup, high and firm; buttocks kept tight with swimming and volleyball, but I felt like a plain Jane compared to all the other women I knew who lusted after him.
Why he would fall for me when he could easily have twenty or thirty lovelier women panting for him, ready to give him whatever he wanted, whenever he wanted it, I had no idea; but somehow, he did. I wouldn’t even date him the first five or six times he asked. I figured I’d be another notch on his bedpost and had no desire to join the scads of other girls who’d ended up there. If not for his persistence and light hearted efforts to keep me entertained with his attempts to woo me, I never would have started dating him. On the whole, he was a gentleman and never pushed too hard to have sex which is why I ended up loving him and engaged to be married.
“Do you love me, Tan?” I suddenly asked.
“I love you more than life itself,” Tan replied. “I wouldn’t marry you if I didn’t love you.”
“I want to wait,” I explained for maybe the hundredth time. “I want to come into our marriage as a virgin. I don’t want to have sex until our wedding night. You know I love you, but this is very important to me. I’ve saved myself for this long, I’m not going to buckle with a week left to go. Please, quit asking. I want our first time to be when we’re married, and not a second before.”
“What about a blow job, then,” Tan laughed. “Sucking my cock won’t harm your virginity, will it? All I’m asking for is a little relief.” He pursed his lips and pretended to be sucking on something cock sized in his mouth.
“Eewwwh! Technically not, but what is it about men and blow jobs, anyway? It sounds disgusting. Sucking on the same thing your pee comes out of. I hope you won’t expect it too often. Maybe on our wedding night, your birthday and our anniversary. I can’t see me doing it more often than that, and I’ll expect you to wash yourself thoroughly beforehand.”
“You should try it, you might like it,” Tan said. “Just as I expect you’ll like it when I lick your cunt.”
“Please don’t call my vagina a cunt. It’s crude and disgusting and it’s demeaning.”
“What do you want me to call it; your pussy?”
“Even that’s rude,” I said. “Why can’t you call it a vagina?”
“Because saying I want to lick your vagina doesn’t have the same impact. What do you and your girlfriends call it?”
Together, we called it a lot of things; kitty, vajayjay, sex, down there; Tiffany called it her fur pie, though why she did, I don’t know, because there was barely any fur on her. A slim little landing strip no more than a half inch wide leading to her treasure. Donna called it her man trap on occasion, and Yvonne did call it a pussy. It wasn’t as if I was naive about my vagina and it’s purpose.
I was more naive about a penis. I’d walked into the bathroom by accident once while Dad was peeing. I’d quickly backed out apologizing profusely, but the image had been burned into my brain. I’d never seen a naked erect one, though I’d felt them pressed against me on the other side of clothes, as I danced with a boy or kissed one. I hadn’t even seen Tan’s, though he convinced me to touch his under his pants once. I only touched it for maybe fifteen seconds, but I still remembered vividly the way it felt. The heat, the hardness of it, the softness, like velvet over steel. I’d pulled my hand out of his pants suddenly like it burned my hand. I hadn’t even watched porn. Dad told me porn never accurately depicted the sex act. It was designed to titillate, mostly males, not instruct.
Tan had asked me once how I’d know what to do with it on my marriage night. I told him I’d talk to people with more experience. He asked who I would talk to and I said I could talk to my parents, plus Tiffany, Donna, and Yvonne were all sexually experienced and happy to give me a word of advice.
Mom gave me “the talk” when I was fourteen. She’d been an unwed mother and didn’t want me making the same mistakes she did. My step-father married her despite a three year old child and I loved him like a real father. He’d never been anything other than good and kind to a fatherless waif. After Mom gave me the talk, Dad talked to me as well, but approached the matter in an entirely different manner than Mom did.
“Look, sweetie,” Dad said. “Mistakes happen. I will never love you less if you decided you didn’t want to wait until marriage, but I would encourage you to be careful and do your utmost not to get pregnant. I know there are a lot of things you want to do with your life, and those things become so much harder if you have a child. I will say this, however. Sex is a lot more meaningful, and even more beautiful, if it’s shared with someone you love. I can think of no greater gift you can give a man than wait for your wedding to share yourself with him and him alone. Unless of course, you fall in love with a woman, then I suppose I don’t need to have this talk with you.”
“Dad!” I complained “now you’re just teasing me. You know I’m not into girls.”
“You’re still young. A lot of things can happen before you’re an adult. It’s okay, whatever you decide. Your Mom and I will love you no matter what. It’s far more important you be the best person you can be rather than who you decide you want to spend your life with.” He hugged me then, and gave me a kiss on the cheek, and I knew he was right; my parents would always love me.
I sighed. “I would prefer you call it a vagina, because that’s what it is, but if you have to call it something else, call it my kitty.”
“Here, kitty, kitty, kitty. Would you like to swallow a little mouse?” Tan said, grabbing his penis in his jeans and holding it, molding his pants over it. It was hard. I’d felt it rubbing against me as we made out.
I laughed. “Your mouse will have to wait another week, just like the rest of you. Where are you and the boys going for your bachelor party?”
“I think Geoff has got a visit to a strip club planned. Lot’s of booze, I’m sure; and he told me to be sure I had a lot of ones, fives and tens with me.”
I kissed him. “Just remember, honey,” I said. “You may look all you want, but do not touch. You can wait another week and I’m yours.” I waived my hands up and down my body. “Everything you wanted for so long is all yours, and yours alone. I’ve never shared it with anyone else.”
“I can’t even have a lap dance?”
“You can have a lap dance,” I said. “Just keep your hands to yourself. They don’t need to wander for you to have a good time.”
“Where are the girls taking you for the bachelorette party?”
“We’re going to Tiffany’s house,” I said. “She’s throwing the shindig. I’m sure I’ll be getting some gag gifts and there’ll be drinking, of course. I haven’t heard all of what they have planned, but it will be somewhat raucous, I’m sure, since Tiffany is throwing the party. She’s not the wildest of my girlfriends, but she’s not far from it.”
“I’m a little surprised you have some friends who tread on the wild side. You’re so straight laced,” Tan said.
“I try not to judge a book by its cover,” I replied. “I’m more concerned with their loyalty, friendship and love than I am in their conduct. If I totally judged book covers, I’d never have dated you. You had a reputation as a lady killer who loved and left them. Heaven knows, every woman of my acquaintance drools over your body. You could have anyone you wanted and I couldn’t imagine you wanted me.”
“You sell yourself short all the time. You’re a tall, classy, beautiful woman, intelligent, funny, self-deprecating. You even know how to cook. The only thing I don’t know about you is how compatible we’ll be having sex.”
“I know love isn’t an indicator of sexual compatibility, but I love you a lot Tan and if love has anything to do with it, sex will be just fine.” I patted his cheek. “You’d better get ready. Your boys will be waiting for you.”
We still didn’t live together. I didn’t trust myself to behave if I had to live with Tan while waiting to wed. We had picked out a nice apartment together and Tan moved in without me. I’d given notice on my own small studio apartment and would move in with Tan after we returned from our honeymoon. He kissed me and left, still sporting a large bulge in his jeans. I wondered if he’d have to masturbate to get rid of it before he went out. He might want to do it a couple times before going to a strip club, or he might get a severe case of blue balls. He told me once being engaged to me was like being married to his hand. He said he had to masturbate all the time just to ensure he didn’t get a case of blue balls. I didn’t know what he was talking about when he said it and I asked him what he meant.
“Look it up on the web,” he replied. “You’ll know what kind of problems I have to put up with being engaged to you.”
I did look it up. It sounded painful. I apologized after reading about it, but instead of offering to help him, said he could go in the other room and masturbate if he was starting to experience pain. He asked if he could do it in front of me and I told him I might be tempted to help him out and I wanted everything to be new when we finally had sex. He did leave the room a few times afterward and I had no problem with it, not wanting him to be in distress.
He came back into the room once after leaving to take care of himself and said, “I’d like to introduce you to my new girlfriend.”
“What new girlfriend?” I asked, shocked.
He stuck out his hand and said, “I’d like to introduce you to Rosy Palms.”
It took me several seconds to figure out the joke, then I took his hand and said, “Pleased to meet you, Rosy. Please take care of our boyfriend. I don’t want him to suffer.” We both laughed and he hugged me. “You sure are a persistent cuss,” he said.
After Tan left, I showered and shaved my legs and underarms. I picked out what I was going to wear tonight. Since it was going to be at Tiffany’s house, I figured casual was fine, some shorts, a blouse, standard bra and panties, strappy sandals. I would put my shoulder blade length hair in a pony tail and add a little make-up, nothing much, a little lipstick and mascara. Yvonne was going to pick me up and take me to Tiffany’s. Since there was going to be a lot of drinking, we all planned to spend the night at her house so no one would drive drunk, so I had a some pj’s picked out as well. I even had some food to ameliorate the affects of the alcohol I knew I’d be having later, but not too much as I expected lots of snacks.
Yvonne was there at seven. “Hey, girlfriend, you ready to go?” She gave me a quick hug and a peck on the cheek.
“Let me grab my overnight bag and I’m ready.”
I snagged it off the kitchen counter and followed Yvonne out the door, locking up behind me. Climbing into the passenger seat, I asked, “Do you have any idea what Tiffany’s got planned for tonight?”
“Not a clue, honey, but I do know it will be fun. Tiffany knows how to throw a party.”
“How many people will be there?”
“I’m pretty sure it’s just ten of us,” Yvonne said. “Tiffany, and your other three bridesmaids, including moi. Let’s see, Erin and Shizuko from the volleyball team, your swimming buds, Maria and Cheyenne, Tan’s sister, Sydney and you.”
Tiffany was my Maid of Honor. She was the wealthiest of my friends, though she never lorded her money over us. She was my closest friend; I’d known her since high school. The rest I’d met in college. Yvonne and Donna had been my dorm mates my freshman year of college. They were two of my bridesmaids, along with Terence, who’d lived across the hall. When we finally outgrew the dorms, we all shared a run down house together off campus.
Erin and Shizuko played on the volleyball team with me, plus they were openly gay and lovers. Erin was a year ahead of me, Shizuko a year behind and Erin was the only one of my friends taller than I was, nearly 5-11. She was the primary spiker on my team, Shizuko, or Suki to her friends, the setter. Maria and Cheyenne swam with me in college. Maria’s family had some money, but she was as relaxed about it as Tiffany was. I suspected she might be gay, because I never saw her with any guys. On the other hand, I never saw her with women either, so maybe she was asexual. I guess the rest of us would be considered middle to upper middle class except Cheyenne, who was at the lowest end of the middle class spectrum, getting to school only because she got a swimming scholarship. Erin, Donna and Cheyenne were African-American, Suki was Japanese-American and the rest were WASP’s except for Maria, whose family was Catholic and Italian-American. It was a fairly eclectic mix of people, but we all got along well with each other, laughing and joking about our differences.
Sydney was the one I knew the least, since I hadn’t met her until I started dating Tan. She was my age, though she hadn’t attended school with us, going to Brian’s Mall. She had joined our group about two months before Tan and I got engaged and got along with everyone like she’d been with us from the beginning.
Tan’s family had a substantial amount of money too, so both he and Sydney were accustomed to the creature comforts. He had a good paying job at an architectural firm and didn’t need additional income from me, so he convinced me to quit my low level job at the accounting firm where he met me to concentrate on being a wife and mother. We’d talked it over and thought three children would be the perfect number. I figured I’d give it about a year or two to get used to married life before adding our first baby to the mix.
Tiffany had a 2800 foot condo on the top floor of a Midtown building near the Downtown CBD area. I know it had cost over 1.7 million dollars. It had two story windows and was absolutely gorgeous. When Yvonne and I got there, we were to last ones to arrive. Everyone else was there and already working on their first drinks.
“Brenda, baby. You decided to join us. Good thing, since you’re the guest of honor,” Tiffany said. “Come on in.”
I walked in to what would become the worst nightmare of my life.
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