Please read Richard's Tales: Scoring the Coach before this one. Hillary thought her cheating was done, but someone heard them.
Hillary looked at Richard as he fell asleep, she shook her head slowly as she grabbed a towel and headed towards the door leading to the locker room. She usually doesn't shower here, but after that sex session she figured she would.
She entered the shower, feeling a little bit of Richard's cum still seeping out of her. She quickly showered up, making sure to get her freshly fucked pussy clean of the cum. After she finished in the shower, she toweled off and walked back into the office.
Richard was awake, still naked and sitting on the edge of the desk, when she entered and he grinned at her, "that was the most incredible sex I have ever had." She laughed lightly, "glad I could be of assistance," speaking almost a scowl.
She quickly got dressed in her calf-length dress and blouse. She put her heels on and grabbed her jacket. She turned to Richard as she opened the door to leave, "this never happened."
"What never happened?" Came a male voice from outside of the room. Hillary jumped at the voice and looked towards the voice. Doug Jacobsen, the boys basketball coach and math teacher, was standing just outside of the door.
Doug is a 51 year old married man. He stands 6' tall, with a bald head and hazel eyes. He has a slender build, weighing about 165lbs.
"Oh hi Doug," Hillary said, looking up at him. Doug looked down at Hillary and said, "hi Hillary, so what never happened?" Hillary half smiled at him, "nothing Doug."
"It didn't sound like nothing, who were you talking to?" He asked, looking in the office and seeing Richard there, still naked. He lifted his head at Hillary, "oh that never happened."
"Yeah, so can you move so I can go home now?" She asked, trying to squeeze between him and the doorway. "That depends," Doug said, not budging. She continued to struggle with him, but stopped after he spoke, "depends on what?"
"What will you do to keep me from telling Brad?" Doug asked, grinning devilishly at her. "Nothing happened," she quickly answered. Doug lifted his head again, "that's not what it sounded like earlier, and he's still naked." She looked at him in horror, "you wouldn't dare." He nodded, "try me."
Hillary lowered her head in shame, "what do you want from me then?" He chuckled lightly, "I think you know the answer to that already." She slowly nodded, "you want to have sex with me too." Doug smiled at her, "yep and I think Richard would like to join us as well."
Richard looked at them when he heard Doug, 'he wouldn't mind having sex with the vixen again,' he thought to himself. Hillary slowly backed up into the office as Doug followed her and closed the door behind him. "So was this young girl any good Richard?" Doug asked as he took off his t-shirt. Richard slowly nodded at him as he looked at Hillary. He could tell Hillary didn't want to do this.
"This isn't right Doug," Richard said, trying to help Hillary out. "You say that after you just fucked her?" Doug responded. "It was a mistake, I seduced her," Richard answered. "Well I'm seducing her now, and you can join in as well," Doug said. "It's not seducing, if you're blackmailing her, besides you're married as well," Richard said. "Yeah to a woman I haven't had sex with in years," Doug responded, as he slid his shorts and underwear down.
As Doug stood back up, Hillary let out a light gasp as she saw his semi hard dick. Doug's uncut dick is 7 1/2" long when fully hard, but was bigger around than Richard's, almost 6" circumference. Doug chuckled when he heard her, "what's wrong Hillary?" She looked at his fat cock in awe, speechless.
Doug slowly started to stroke his dick as he looked at Hillary, "time for you to show me what your hiding now." Hillary started to unbutton her blouse as Richard glared at Doug, he wanted to help Hillary stop this, but also didn't want her husband finding out about him, so he remained silent.
Hillary removed her blouse, and unhooked her bra, tossing them aside. She pushed her dress and panties down and stepped out of them. "Very nice," Doug said as he continued stroking her hardening member, and stepped towards her. He looked down at her as he moved his other hand to cup her pussy, "so you let Richard blow his load in you?"
Hillary slowly nodded at him as her body trembled in fear. "Such a dirty girl," Doug groaned as he rubbed her slit up and down, roughly. Hillary's legs began to shake as his thumb found her clit and rubbed it vigorously, "you like being called a dirty girl huh?" He growled in her ear. She shook her head slowly as she felt herself getting turned on again.
"Ha don't lie to me, your pussy is telling me otherwise," he almost yelled as he slid his middle finger into her. Hillary let out a low moan of pleasure as she pushed her hips into his hand.
Richard watched the action in front of him as his dick slowly began rise again. He slowly stroked it as he watched Doug start fingering Hillary's pussy.
Hillary started moaning louder as she ground herself into Doug's hand. Richard didn't know if she was actually enjoying herself, or if she was just doing it to please Doug, but she was putting on a good show if she was faking it.
"That's such a dirty little slut, enjoying yourself aren't you?" Doug growled. Hillary responded with a loud moan of yes as she wrapped her hand around his dick and started stroking it. Doug threw his back as he fingered her pussy, faster and harder. As Hillary's hips started bucking into his hand, he abruptly pulled his hand away from her pussy and smiled, "not so fast missy."
Hillary looked at Doug with a want in her eyes, she wanted to cum again, but he had denied her. "You can't cum until I say you can," Doug said grinning. He pushed her hand away from his dick, grabbing her arm, and leading her to the desk.
Richard got up and move aside as Doug led her to the edge of the desk. He helped her up and laid her back, so her ass was on the edge. Doug lifted Hillary's legs up to her chest and commented, "nice and flexible still, I see." He moved to his knees and looked at the folds of her slit, glistening with her juices, "looks delicious," he said.
Richard watched Doug as he stuck his tongue out and ran the tip through her slit. Hillary's body shuttered as she moaned in pleasure. Richard moved to the side of the desk, not wanting to be left out and presented his dick to Hillary.
Hillary looked at Richard with that lusty look again and opened her mouth. Richard guided his dick into her mouth and she wrapped her lips around the head of it. As Doug started eating out her pussy, she moaned more, sending shockwaves to Richard's balls.
Richard started moving his hips into her as she took more of dick into her mouth. She pushed her mouth onto his dick, until the head hit the back of her throat. She started choking, staying there for bit, then she pulled back to breathe again.
Doug was sucking hard on her engorged clit, and flicking his tongue against it, causing her body to tremble more as her orgasm began to build.
Richard shoved his hips forward again, pushing his dick into her throat again. She gagged on it as he held her head in place for a bit with his hand. Richard normally never did this to a woman, but he was so turned on, being able to fuck her again, he didn't care.
Hillary's moans were getting louder as she pulled away from Richard, after he let go of her head. "Oh my god, I'm gonna cum, yes make me cum," she moaned as she grabbed Doug's head to pull him into her. He resisted though and pulled away from her. Hillary looked at him with a pleading look, "why did you stop?"
Doug chuckled as he stood back up, "I told you, you can't cum until I say you can." Richard noticed Doug's dick was leaking pre-cum as it bounced in front of him. Doug looked at Richard, "you want in her pussy now?"
Richard nodded quickly as he moved to the foot of the desk. Doug stepped aside and whispered, "pull out before she cums," into Richard's ear. Richard nodded as he guided his dick to her sopping wet entrance and sunk into her easily. Hillary let out a long groan as she used her pussy muscles to squeeze his dick again.
Doug moved up to her head as he offered her his dick, "show me what your dirty mouth can do," he groaned. She looked up at him and reluctantly opened her mouth. Doug guided the head into her mouth and let out a loud groan as she wrapped her lips around it. Doug started to push his dick into her mouth further, stretching it almost to the limit with his girth.
Richard started fucking her pussy slowly, sliding almost out, then sinking balls deep back into her. Her pussy squeezed his dick each time he buried himself in her. He looked down at their union, and noticed her clit was much more engorged than before. He wanted to rub it for her, to make her cum, but he didn't want Doug to kick him out. He started to move faster with each stroke, as Hillary started moaning more and more around Doug's dick.
Doug's groans were getting louder as he moved his hips into her bobbing head, "that's a good slut, suck my dick."
Hillary sucked hard on him as she felt her orgasm building again. She wanted to cum so bad now, but didn't know what Doug would do if she did, so she put hands on Richard's hips to push him away before she did.
Richard knew why she had put her hands on his hips and pushed against him. He quickly withdrew from her, his dick glistening with her juices. He looked at her hole, it making a sucking motion with the muscles, closing almost completely, then opening back up. He wanted to slam back into her and fuck het hard until she came, but Doug was looking at him now.
"Did the slut cum yet?" Doug asked, looking Richard in the eyes. Richard shook his head as he looked back to Hillary's sucking hole. "Good, now the real fun begins," Doug said, as he laid on his back on a rug in the middle of the floor. He looked at Hillary, "ok my turn to get in your tight cunt now," he said as he motioned her over.
Hillary reluctantly got off of the desk and walked over to Doug. She stood over him and slowly moved to her knees, straddling his hips. She lowered herself, until the tip of Doug's dick rubbed against her slit, she grabbed his shaft to hold it steady as she tried to work herself onto it. The lips of her pussy spread apart as the head of his dick began to enter her.
Doug let out a loud groan of pleasure as he felt his dick entering her. Hillary took deep breaths, trying to relax as she slowly lowered herself onto it. Her pussy was being stretched more than it ever had before, as Doug's fatter dick went into her fully. She rested with her ass on his thighs, giving her pussy time to adjust to Doug's dick.
Doug wasn't about to wait though, he put his hands on her shoulders and pulled her upper body to him. She tried to fight it, but gave in and laid on his chest. Doug moved his hands to her ass cheeks, pushing his hips into her, to lift her up. He held her ass cheeks hard, then without warning, started slamming into her hard. His thighs slapping against her ass hard as he lifted his hips into her, burying his dick into her.
Richard moved up behind Hillary, standing by Doug's feet, watching them. He could tell Hillary's pussy was stretched to the max, as Doug lowered his hips down, her pussy clung to it, as if being turned inside out. Doug was fucking her harder than he had earlier, really slamming into her hard. Doug pulled Hillary's ass cheeks apart every time he slammed into her pussy, giving Richard a good view of her puckered asshole. He wanted to get behind her and fuck her ass at the same time.
Hillary started moaning as her orgasm began to build again, "oh my god your dick is so big, fuck me baby, yes." Doug was grunting as he fucked her, lost in his own world of pleasure. "I'm gonna cum baby, yes let me cum," Hillary moaned in his ear as she moved her hips into his upstrokes.
Doug pounded into her even harder as he groaned, "yes, cum for me, cum all over my dick." He let her push herself up as she started riding his dick faster. She moved her hand to her clit and started rubbing it vigorously. With one final downstroke she froze in place as she moaned loudly, "holy fuck yes here I cum." Her body thrashed wildly on him as her orgasm shot through her body, her pussy squeezed Doug's dick hard as pussy juice flowed out around it, soaking his ball sack and abdomen, and running down onto the rug.
Doug tried to fight his own ejaculation, but it was useless since it had been so long for him. He yelled out as his dick throbbed and fired into her sucking pussy. Hillary felt his dick throb and ejaculate into her, setting off a smaller orgasm in her as she slowly rode his dick.
Richard watched as Doug's dick throbbed and shot more cum into her, wishing it was him blowing in her again. He watched as Doug's cum started leaking out around his throbbing dick, mixing Hillary's juices on the rug below them. He was stroking his dick vigorously as the pair in front of him started coming down from their orgasms.
Doug's dick continued to throb in Hillary's pussy. His breathing was slowly going back to normal as he looked at her and smiled, "oh my god Hillary thank you."
Hillary gave him a half smile in return as she slowly lifted herself off of him. As his deflating dick slipped out of her, some his cum clung to the head of his dick and her pussy, breaking from her as she moved off of him, kneeling beside him.
Richard quickly moved behind her, pushing her onto her hands. Without caring he quickly sunk his dick into her pussy. She felt extremely wet to him as he grabbed her hips and started pounding in and out of her. Doug's cum was leaking out of her as he slammed into her hard and fast.
Hillary didn't expect Richard doing this, but she knew he had just watched her and Doug. As Richard was fucking her from behind she turned her head to look at him, "I want you in my ass please."
Richard couldn't believe what he had just heard, "what?" She started moving her hips back into him as she repeated, "I want you in my ass. Fuck my ass please."
Richard stopped his movements staring at her in awe, "are you serious?" She nodded at him, "yes." Richard pulled his dick out of her pussy, Doug's cum and Hillary's juices covering it. 'I wanted to just do that, but didn't think she would like it,' he thought to himself.
Hillary laid her chest on the floor and reached under herself, collecting the leaking juices from her pussy. She then rubbed it onto her puckered asshole, covering it with the juices. She grabbed her ass cheeks and spread them apart, presenting her asshole to Richard.
Richard moved higher on his knees and guided the tip to her hole, "are you ready?" Hillary nodded and started taking deep breaths. Richard held onto his dick as tried to push into her forbidden hole. Her anus slowly began to open as he pushed slowly. Hillary let out a low moan as she felt the head of his dick slip past her sphincter. Inch by inch, Richard slowly pushed his dick into her bowels.
Hillary tried to relax herself, breathing deeply as Richard continued to enter her anus. Richard pushed until his lower abdomen rested against her ass cheeks, he stayed there enjoying the feeling of her sphincter opening and closing around the base of his dick, and rectum squeezing the shaft and head of his dick. This was only the second he has ever done anal, and he had forgotten how it felt.
He held on to her hips as he slowly began to withdraw, her rectum almost pushing him out of her. The head of his dick remained just inside of her sphincter, as he watched it contract and relax around it. He slowly pushed himself back into her bowels again, her rectum squeezing tight, as if denying entry.
When he was fully in her ass again, Hillary looked at him and moaned, "oh yeah, fuck my ass please." Richard started a steady rhythm, pulling out until he was just inside of her ass, then sinking back into her. As he kept moving in and out of her, Hillary started moving her hips into inwards thrust, wanting him to go faster.
Richard got the idea and started moving faster with each stroke, slapping his lower into her ass cheeks with force. Hillary started moaning louder as an orgasm wad building in her, moving her hips into him harder and harder. She held her head down as she rubbed her clit with her hand hard.
Richard knew she was close to cumming, and he felt the familiar feeling in his balls as well, as they started to tighten up. Hillary's moans were turning into screams as she yelled out, "oh god yes, fuck my ass, yes make me cum." Richard felt her ass squeeze his dick with death grip, making it hard for him to move.
Hillary screamed as her orgasm rocked her body, "ooohhhhhh." Juice came flying out of her empty pussy, a mixture of her juices and Doug's cum, flying out and soaking Richard's legs. Her rectum squeezed and released his dick, as she came.
Richard felt his cum rushing up his shaft as his dick throbbed and fired deep into her ass. He pulled back until he was just inside of her, as his dick throbbed and shot more cum into her. This orgasm wasn't as intense as the earlier one for him, but it was still satisfying, as he grunted with each shot of cum.
Hillary orgasm continued on as she felt Richard unloading into her bowels, squirting more juices out as she continued rubbing her clit.
Richard's dick continued to lightly throb as he collapsed onto her back, breathing heavily. "Oh my god," he groaned out through breaths. Hillary was breathing heavily as well, unable to talk but moaned, "uh huh."
Richard finally got the strength to push himself back up, he slipped his dick from her asshole. He looked at it, still gaping a little as it open and closed to the emptiness. A small amount of his cum was pushed out by her rectum, running down to her inflamed pussy lips. Richard smiled to himself as he stood up to gather his stuff.
Hillary was unable to move for a while, totally exhausted now. Her asshole continued open and close as she pushed herself up with her hands. She felt the need to fart now and pushed a little, a wet fart came from her ass, as more of Richard's cum was forced out, running down her pussy lips. She looked between her legs and saw dried cum on her inner thighs from Doug, as well as her own.
No more of the coach, unless I get some ideas from readers. I do have more of Richard's tales if you would like. Let me know. Constructive criticism please.