3 comments/ 17032 views/ 15 favorites Life After The Office By: wowsex "That's a wrap!" She had heard it countless times over the past nine years but this time there was some finality in it that hadn't been there ever before. That's because The Office had just shot the final scene of their series finale and now Jenna Fischer started to ponder about what she wanted to do next. Oh sure, she had a new baby and relatively new husband at home and that would keep her occupied for awhile but she knew she was going to miss the fun of being on set every day. Now the fun wasn't just hanging out with her best friend Angela Kinsey or reminiscing about the greatness of St. Louis with Ellie Kemper but it was hooking up with random temps, cameramen and even John Krasinski. The last of which had led to her divorce. Now granted when her ex-husband had filed for divorce, he didn't know that she was banging John. He had actually thought she was fucking Seann William Scott during filming of The Promotion but that had never been the case although her husband refused to believe it and filed for divorce a short time later. This had set her into a rut until she met a very nice temp when she was waiting between scenes on The Office. With restored confidence after this encounter, she had met a new man, got married, and had a newborn baby waiting at home. But now with her TV series over and approaching the Hollywood death age of 40, she knew she was close to falling into that rut again. With that mindset, she received a call from her agent who said that a new off-Broadway play in New York wanted her to audition for the lead role and they wanted her to fly to New York as soon as possible. A few days later, she gave her husband a long and sloppy blowjob, played with his balls a little, let him cum in her mouth, and kissed his dick goodbye. She had been good since she had gotten remarried but Jenna was determined to return home with the role and to do whatever it took to get it. As she sat on the plane, she pondered how far she was willing to go for the role. To get her big breakout role on The Office, she had to suck a producer's cock and even though she was married at the time, she didn't really care about cheating on him too much since her first husband was a bit of an asshole. That's why she divorced him she thought to herself "but can I really cheat on my new husband? After all, he has always been so nice and caring to me. He gave me a child and I've wanted to be a mother for the longest time. He's always quick with a joke and always backs me up with whatever I want to do. He was really Prince Charming, he was above average in every way. That is except one and that one was in the anatomy department where he was average. Now his nearly six inch penis usually made her cum but it was never earth shattering and sometimes a girl just wants to be bad and have a big cock in her. Anyway I've been good since I re-married so I can afford to have a little fun on this trip," Jenna reasoned with herself as she saw the bright lights of New York coming up over the horizon as she looked out of the window of the plane. She checked into her New York hotel at around six in the evening with her audition set for eleven the next morning. After putting her luggage in her hotel room, she figured she would grab a quick bite at the hotel bar before getting a good night's rest for tomorrow's big day. As she took a seat at the bar and ordered her dinner, she noticed a cute guy maybe ten years younger than her, stealing glimpses in her direction. She gave him a quick smile and eventually he made his way over to her. "You look like my favorite celebrity crush, may I buy you a drink?" the gentleman asked. "What celebrity would that be? Amy Adams?" Jenna replied. The guy laughed and said, "no, Jenna Fischer. I've had a crush on her ever since I started watching The Office and she still looks fantastic even after having a baby. So what's your name." She responded and after he got over his stunned reaction, Jenna smiled at him and asked, "what is your name and do you want to eat dinner with me." "Andrew," he responded "and of course but only if I can buy you a drink." "Agreed," Jenna said. After a few drinks and a fun and lively dinner where Jenna recounted why she was in New York to begin with, Jenna thanked him for a wonderful dinner but that she had better be going back to her room. Then Jenna had a thought that she hadn't had in a long time. She didn't know if it was the alcohol or the fact that a cute guy had been hitting on her all night or something else entirely but even she was a little surprised at what she did next. She leaned into Andrew and whispered into his ear, "Do you want to come up to my room for a nightcap?" Stunned Andrew replied, "If you don't care that you're married then I don't care." Jenna gave him a sly, dirty little smile and they were off for the elevator hand-in-hand. Jenna shut the door behind her as they entered her hotel room and playfully pushed Andrew onto the bed. She then proceeded to do a playful striptease for him. She took off her dress and stilettos while she gently swayed back and forth in her black lace bra and panties. The only thing going through Andrew's mind at the moment was how amazing Jenna looked in her outfit and how he wished this moment would never end. She may have had a kid but her ass still looked amazing and her boobs were probably a little bigger since she had her kid. In short Jenna Fischer looked sensational. As Jenna rocked her body, she slowly untied her bra and let it fall to the ground revealing her big breasts that only had a hint of sag. "Do you like?" She softly asked Andrew. "I love them," he said. Jenna smiled and went to kneel before him, gently undoing his belt and pulling down his pants. She slowly began to stroke Andrew's hard seven inch cock as he let out a soft moan as his dream girl was now playing with his cock in the flesh. He could see her wedding ring in the hand that was jerking him off and that turned him on even more. While Jenna continued to stroke his cock, he reached out and played with her tits, gently kneading them in his hands. This caused Jenna to moan and she leaned in and took his cock into her mouth gently sucking on it. Andrew let out a moan and lightly thrust his cock forward causing her to take more of his dick into her pretty mouth. "I never knew Jenna Fischer was such a hot sexy cocksucker," Andrew let out and all Jenna could do was let out a moan as she had nearly all of this stranger's cock in her mouth. After what seemed like forever but was probably just a few minutes, Jenna took her mouth off Andrew's cock and softly pushed him onto the bed. She straddled her lover taking his cock in her left hand with her wedding ring glistening in the pale moonlight. She slowly guided his cock into her warm waiting pussy and gently eased herself onto throbbing cock. "Oh fuck, it's been so long since a cock's felt this good in me," Jenna cooed and picked up the pace as she rode her man. "You're so warm and tight, this feels so fucking amazing," Andrew gasped as he met Jenna's bouncing pussy with upward thrusts of his own. Jenna could feel her own orgasm approaching as she rode him cowgirl and she panted that, "I'm gonna cum soon, oh fuck keep fucking me." "I'm close too, where do you want me to cum?" Andrew asked. "Cum in me, I want you to fill me up," Jenna responded not caring at that moment that she wasn't on the pill and that the dick she was riding wasn't wearing a condom. But at the moment, she was so close to a great orgasm that she didn't really give a fuck. At the moment, Andrew noticed Jenna's neatly manicured fingers were rubbing his chest and he loved seeing her wedding ring shining on her left hand. The pure naughtiness of the situation was enough to put him over the edge and his cum exploded out of his dick and into the actress's wet pussy. Jenna felt him burst into her and she screamed, "Oh shit, you're pushing me over the edge, here I fucking cum." "Oh yea cum all over my dick baby," Andrew shouted "Oh fuck yes," Jenna screamed as she gushed all over his dick. "God, I haven't had a cock that big in a long time' Jenna told me, "My husband's is really average, he was able to give me a baby but that's about all it has been good for." Jenna then rose off his cock and moved down to the other end of the bed where she licked his cock clean. She then returned to his side and cuddled in his arms. As they both drifted off to sleep naked in each other's arms, Jenna realized that she had just let a stranger cum in her unprotected pussy but she couldn't be bothered to care at that point. And besides what they had just done was so hot and naughty that nothing could ruin the high she had just experienced with some guy she had just picked up in a hotel bar. The next morning Jenna awoke Andrew with a kiss and took a long hot shower. After she was finished she toweled off and returned to her room where Andrew was just getting dressed himself. "Thanks for the wonderful night and hopefully the next time I'm in New York we can meet up again," Jenna said to her lover. "I'd like that,' he responded "How do you feel about your audition?" "I feel pretty good but I'm still pretty nervous," Jenna admitted. "Why don't I help you with that," Andrew said as he reached for her towel and took the only piece of fabric between him and Jenna's MILFy body. He gently laid her down on the bed as she cooed gently and put one hand on her breast and a finger in her rapidly moistening pussy. He started putting gently kisses on the side of her neck while rubbing her tits and fingering her wet pussy. He heard Jenna beginning to moan as he moved from her neck inching closer to her pussy while planting soft kisses as he went. He soon reached her pussy and licked her pussy slowly up and down. "Faster," Jenna cooed and he not only did that but put two fingers in her as he licked her cilt with his tongue. Soon her juices were flowing out of her pussy as she moved her body toward Andrew's tongue while her pussy starting pulling in his fingers. "Oh my God, oh fuck, oh yes, don't stop, I'm almost there, YES!!!" Jenna screamed as she exploded all over his fingers and tongue. As Jenna started to come down from her high, a sense of ease came over her. "Thanks for that, it's been a long time since anyone has eaten me out like that," Jenna told Andrew "I know you're going to kick that audition's ass," he said while giving his phone number to her as he got up to go. "Thanks again for everything," Jenna said and she gave him a nice kiss goodbye. With that, Jenna got dressed and set out for the theater. She walked into the theater with a renewed self-confidence and she knew she was going to nail this audition. Inside the theater, she met Neil who was the writer/director/everything of the play and he gave her the scene that he wanted her to act out. As she got up on the stage, she looked out at the theater and couldn't wait to be onstage for opening night looking out at the packed house that would be cheering for her and her cast mates. But for now there was just one man that she had to impress and she looked right at him as she started to act out her lines. As she recited her lines, she knew by Neil's facial reactions that she was knocking it out of the park. Once she was done, Neil asked her to step into his office. "Listen, your audition was great and I want to bring you into the cast but there have been other good auditions and I need to know you are going to be a team player," Neil told her matter-of-factly. "I will be a team player and I can prove it," Jenna said sultry letting down a strap on her dress and moving around to Neil's side of the table. With a smile, she removed her dress and sat down on Neil's lap. They began to make out with their tongues exploring each other. Soon, Jenna reached for Neil's cock and she took it out from his pants. She stroked it up and down and soon Neil's penis stood seven inches erect. They continued to explore each other's bodies for some time with Neil taking a particularly liking to Jenna's boobs after he had removed her bra. The married 50 year old father of two soon picked Jenna off his lap and gently made her kneel in front of him. She knew exactly what he wanted never taking her stroking hand off his cock as she removed his pants and began to gently play with and suck on the playwright's balls. After doing this for a couple minutes, she moved to his dick and slowly started to suck on the above average penis. Eventually, she was able to deep throat his entire cock and Neil let out a huge sigh, "no one has been able to take all of my penis in years." Since she had been a teenager, she had always had a huge thing for writers. She had lost her virginity at 16 to her high school drama teacher who of course had written the play she would be in. She had sucked just about all the dicks of the writers, she had worked with in college when she was majoring in theater at Truman State. Her ex-husband had been one, her current husband was one, and the man whose cock she currently had in her mouth was one too. Jenna was really proud of her cock-sucking skills and even more proud that she almost had a new job. She greedily sucked on his dick for another minute as she played with her pussy. Then Neil lifted her up giving her one more deep kiss before he commanded her to sit on his cock. His hands grabbed onto her firm ass as soon as sat on his dick and they looked into each other's eyes as they moved in for a kiss. As their tongues entwined, Jenna began to slowly ride the dick of the man who was going to save her career. As Jenna picked up bouncing, she thought of her family and wondered if everything she had done on this trip was worth it. If her husband found out what she was doing, she would be shamed for life and her son would know that his mother was a cock slut. No different from Paris Hilton or Kim Kardashian. She was soon slammed back to reality as Neil picked her up by the legs with his dick still in her soaking pussy and carried her over to his couch. Yes it was worth it Jenna thought to herself as long as the men fulfill me more than my husband and my orgasms this satisfying then I don't care who knows what a slut I am. "Oh fuck, your cock feels so good inside my pussy," Jenna shouted between their kissing and this just caused Neil to pound her harder "Cum for me babe," Neil ordered Jenna, "Cum all over my cock." "Oh yes babe, keep pounding me, I'm gonna cum all over your big dick, oh fuck!" Jenna screamed as she dug herself deeper into the comfortable loveseat as her juices squirted all over the dick that was filling her up and making her feel so good. Once Jenna came slightly down from her orgasm, she noticed Neil staring at her asshole. "You want to put that big dick in my tiny little asshole, don't you, lover." Jenna giggled, "It's been a long time since someone's put their cock up in my ass," Jenna commented as she seductively waved Neil over with her finger. "Well if you want to guarantee your lead role, I want that amazing ass of yours," Neil told her as he lay on top of her and began to play with her breasts. "Tell you want if you want a chance at my incredible little asshole then you're going to have to cast me first and then I'll think about letting you fuck me up there," Jenna said as she planted some delicious wet kisses on the playwright and she knew that with his dick in the state it was in, she could get him to agree to just about anything right then and there. "And if you agree to that then I'll let you finish in my unprotected pussy," Jenna continued with a sly smile as she felt Neil's dick grow against her leg. "Deal," Neil agreed and they sealed it with an open mouthed kiss. Neil laid Jenna back against the couch and lined up his dick with Jenna's leaking silt. He couldn't believe one of the hottest girls in the business not only wanted to work with him, not only blew him, not only let him fuck her but was going to let him explode his seed into her and had also maybe agreed to let him fuck her in the ass. He rubbed his cock against her pussy which drove Jenna wild and he soon had Jenna going mad demanding he ravish her once again. He pulled Jenna closer to him and raised Jenna's smooth silky legs over his shoulders and eased his dick into Jenna's pussy. As he picked up the pace, Jenna instivectly wrapped her legs around Neil's waist which had the effect of pulling the cock that was already in her warm velvety pussy even deeper into her. Neil continued to pound her and he soon felt close to exploding. Jenna could feel his cock expanding in her pussy and also knew that he was about to cum. Neil lowered his head at the same time Jenna raised hers and as their lips locked, Neil exploded in Jenna's pussy coating it over and over again. This caused Jenna to cum again as they moaned into each other's mouths. They lay there for a few minutes as Jenna let Neil explore her body when Neil said, "You were fantastic Jenna and as soon as I finish my last casting cou... interview, the part will be yours" Jenna gave Neil a nice wet and long open-mouthed kiss and thought to herself that while that was awesome, she had heard stuff like this before only to lose a role she really wanted to that final person interviewing and besides she thought that they had had a deal. "I thought we had a deal," Jenna said slightly perturbed. "I have to do this final interview, it's a favor for a friend," Neil commented. "Well who is the last interview?" Jenna inquired. "Leslie Bibb's coming at three," Neil said. "I got this, Neil, Leslie won't do anal ever," She winked at him. Jenna hadn't done anal since she had remarried but she figured a guarantee of anal instead of just a vague promise would be a great way to seal the deal. As Jenna walked out she turned to look back at Neil and she saw his jaw hit the floor and she smiled to herself as she turned to leave for the airport. As she waited for her 6PM flight to board, she received a phone call from Neil. "Leslie was fantastic and I gave her a role but you were right and you got the main part babe," he said "Then you can expect a lot more of what we've already done," Jenna replied and with a little laugh she continued, "and I always follow through on my promises. As she hung up the phone and got ready to board the plane, Jenna had a huge smile on her face and she couldn't wait for the new adventures that a play in New York would bring. She would have to practice anal with her husband so she could work her way up to the bigger cock she had promised would be up her butt in a few short weeks. She hoped her husband wouldn't suspect anything since she had always adamantly refused to do anal with him and now all of a sudden after a trip to New York wanted dick up her ass as often as possible. "I'll just have to be careful," Jenna muttered to herself as she started to fall asleep on the airplane, "after all no guy's going to complain about hot sex with a woman. Life after The Office is going to be fun and exciting, I think my worn out pussy would attest to that. Maybe being a near 40 year old woman in show business won't be a such a death sentence after all." Life After The Office Ch. 02 "Oh fuck yes, shove your fucking cock deep in my fucking ass," Jenna Fischer wailed. It was a few days before the opening of Reasons To Be Happy, a new play which Jenna would have the lead starring role in. She was currently at her New York home in her bed with her husband's cock penetrating deep into her ass. To get the starring role in the play, she had promised to have anal sex with Neil, the producer of the play, among other things. This had awoken a deep wanton desire in her because she had loved anal sex in college and now wanted it as much as possible going forward. Unfortunately this created a problem for her since she hadn't had anal sex since college and Neil's cock was pretty big. The problem was her husband had pushed for anal before and since she had always steadfastly refused to let him into her tight bunghole and since he was the one she fucked most often, she was going to have to fix this. Her husband's dick was about average size so she figured that would be a good starter cock for anal loving. She didn't think her plan had to be all that elaborate since he begged for it probably at least once a month over the nearly three years that they had been married. And she wasn't that bad of an actress either she reasoned to herself, "after all I've been nominated for an Emmy. A little acting on my part will sell any plan I come up with." So Jenna came up with a plan with the first part being simply taking her husband out for a nice dinner after dropping her son off at the house of her best friend, Angela, for the night. She also made sure she kept her wine glass filled throughout the night which of course didn't go unnoticed by her husband Lee and offered to drive home. On the way home Lee brought up the idea of anal like Jenna knew he would and Jenna played along. "You want my ass don't you babe," Jenna purred as she rubbed her husband's dick through his pants. "Well since The Office ended I've wanted to try new things like the play in New York and I think anal fits into that nicely," she continued as she pulled down the zipper on her husband's pants and pulled out his cock rubbing it slowly with her hand. "Oh fuck yea," her husband moaned from a combination of Jenna's playful hand and the realization that he was finally going to have his wife's virgin (he thought at least) ass. Jenna put her husband's cock back into his pants as they pulled into their driveway. Lee practically jumped out of the car and picked up his wife carrying her upstairs to their material bed. Jenna smiled to herself as she knew her plan had succeeded and her cheating adventures were just beginning. Her husband threw his pants off and pretty much threw his wife onto bed turning her onto her front in the process. Just as he was preparing to enter the hole he had always wanted to experience but never had, Jenna threw up her hand and said, "Hold on there fella, let's get some lubrication on there first." "But my dick's already covered in pre-cum from your sensational handjob in the car babe," he pleaded. "No ifs, ands, or buts, mister," Jenna commanded sternly but playfully. She turned around, pulled her husband close to the bed, and took his almost six inch cock into her mouth as she lay on the bed. She teasingly sucked her husband's ball and slobbered all over his cock. She gave his cock one long deep suckle before she panted, "Put that dick in my pussy and make me cum then my ass is all yours." Jenna's husband lined up his cock with his wife's vagina and quickly buried all six inches into his wife's wet pussy. Lee pounded his wife as Jenna lay back on the bed with her head raised just a little so she could see her husband's dick pound her. She slowly played with her clitoris as her husband continued fucking her and she was soon nearing an orgasm. The all day and all night anticipation of a cock in her ass had gotten her close to orgasm and as she had so often done in the past when being passionate with her husband, her fingers had pushed her over the brink of orgasm. As she watched the cock piston into and out of her pussy, Jenna slightly shuddered as she came with her head gently shooting back, her eyes slowly rolling back into her head and her mouth hanging slightly open. She continued rubbing herself until after the orgasm had rolled through and then she brought her fingers up to her mouth with her wedding ring glistening in her cum juices. "I tasted pretty good if I do say so myself," she thought to herself as she licked her fingers. "Wow, I think that was one of biggest orgasms I've ever seen you have," Lee commented as he slowly pulled of his wife's pussy. "You're right babe, I think it was a combination of the fact I'm about to have a cock in my ass but mostly the amazing fuck you just gave me. It was one of the biggest ones I can remember ever having," Jenna lied to her hubbie although it was probably the biggest one her husband had given her, it paled in comparison to most others she had received including the ones she recently had in New York. "Come here babe," Jenna cooed as she grabbed her husband by the tie and pulled him closer to her giving him a deep kiss, "It's time to fuck the ass that you've always wanted to have." Lee removed the the rest of clothes as Jenna flipped over onto her stomach eagerly anticipating a cock in her ass. He slowly rubbed his dick which was still covered in his wife's juices up and down along his wife's asshole. "Don't be messing with me, Lee. If you want this ass you better stick in it before my buzz wears off and I sober up," Jenna ordered him. "Just having a little fun since you've been making me wait to do this forever," Jenna's husband responded with a smile on his face and with that he accessed the hole that had been forbidden to him for all these years. He slowly pushed his dick all the way in and took in all the sensations he was feeling now that he was finally buried balls deep in his wife's ass. "How does it feel babe?" Lee asked. "I'm not sure if it's the alcohol but it feels really, really good," Jenna answered knowing that her plan had worked and her husband would never wonder why she wanted so much anal in the future ever again. "Yea you like my cock in your virgin asshole?" Lee asked not knowing that Jenna had experimented with anal in college and love it tremendously. "Oh yea my virgin ass loves her new visitor," Jenna sighed. "That's awesome, hopefully we can do this a lot more moving forward," Lee said as he began to thrust in and out of his wife's ass. "I think I'd like that," Jenna moaned her plan now finished and with her ass adjusting to the cock invading it, she wailed, "go faster!" "Will do," Lee heaved as his desperately tried to hold off from cumming too soon although with his fantasy finally fulfilled, it wasn't going to be easy. "Oh fuck yes, shove your fucking cock deep in my fucking ass," Jenna Fischer again wailed. This was probably the first time she was glad her son wasn't home while she was getting fucked since this was definitely the first time her screaming would have woken him up. "Oh fuck yea honey, I'm about to cum, I'm about to cum," Lee gasped. "Oh baby pull out and pour all your hot cum over my asshole" Jenna shouted as she felt another orgasm approaching as she played with her pussy again. "Fuck yes" Lee said as he pulled out and came all over his beautiful wife's ass finally fulfilling his fantasy. As her husband finished on her ass, Jenna pushed herself over the edge as she rubbed herself to completion. Once their breathing calmed down and their composure regained, Lee said, "I can't wait to do that again." Neither can I, honey, neither can I,' Jenna answered. Her husband completely oblivious to the fact that Jenna was thinking her next anal experience was almost definitely going to be with someone else and not him. They drifted off to sleep in each other's arms. The next day Jenna awoke and got herself ready to make good on her promise to Neil. She douched, took a shower, and made herself up into one fine looking woman. She knew that after today's rehearsal, Neil would call her into his office and drive his cock up into her ass again and again. She got wet just thinking about and couldn't wait to experience it again. She left her sleeping husband lying in bed and went off to the playhouse. At the playhouse, she saw Leslie Bibb shamelessly flirting with Josh. Leslie and Jenna had been flirting with their male counterparts since play rehearsals had started but had generally kept it in their dressing rooms. There hadn't been any fucking yet or at least Jenna hadn't been aware of any but she hoped things would progress to that point and Leslie moving the flirting to out into the open could only be construed as a good thing. Jenna had been slightly worried to flirt out in public since she wanted to keep her own indiscretions as quiet as possible but was more than happy to see Leslie doing it. "Leslie can I talk to you?" Jenna asked. "Sure thing," Leslie answered, "I'll be back for this fine butt," She said to Josh and gave it a playful little slap as she walked over to Jenna. "I see you're moving things forward with Josh," Jenna said. "I am and I think that stud will soon be mine and I'll gladly share him with you," Leslie deadpanned causing both girls to giggle gently. They suddenly heard Neil shout, "Places everyone," and the day of practice had started. After a great day of rehearsal, Neil asked Jenna to meet him in his office in a few minutes. "Don't worry I know I'm your alibi for this. If your husband wants to know where you were just have him call me," Leslie said gesturing to Neil's office. "Thanks honey," Jenna responded with a slight smirk. "Enjoy that throbbing dick in your ass," Leslie whispered. "Oh you know I will," Jenna said with a smile. "God I can't believe you love anal sex so much. Well that's why you're the lead and I'm the sidekick. I only let Neil fuck me and give me a creamy facial, you promised him everything," Leslie said. "Honestly last night was the first time I had anal in a long time and it felt so amazing. I'm getting wet just thinking about Neil putting his thick cock in me. "Well have fun. It just feels so wrong and unsexy to have someone put his dick up my poop shoot so I'm going to work on getting Josh to put his sweet cock in my wet pussy," said Leslie leaving Jenna by herself. Jenna opened the door to Neil's office and walked in. "I see you've been getting ready for me. I've been getting wet all day waiting to have your long thick cock in my ass." Jenna purred to Neil who was sitting on his sofa with his pants down at his ankles. "Let me see how good you taste Jenna. I haven't been able to get your amazing body out of head since your audition and whenever I think of your promise, I get hard. My wife is way too religious to try anything but the same old same old," Neil said as Jenna stepped out of her dress leaving her clad only in her bra and panties. Neil slowly removed Jenna's panties gently kissing down her inner thighs in the wake of Jenna's disappearing undergarment. "Smooth, beautiful legs. Just like I remember," Neil said. "Thanks babe but I really need to have my pussy eaten right now," Jenna playfully said. Neil raised his head to Jenna's already wet pussy while placing his hands on Jenna's magnificent 36C tits. He roughly took a breast in each hand kneading her tits between his fingers causing Jenna to moan. While this was going on, he flicked Jenna's clit with his tongue again and again. The contrast between Neil roughly playing with Jenna's boobs and gently playing with her pussy brought Jenna to the edge of orgasm. "I'm so close Neil, make me cum and then I'll let you stick your big cock in my ass," Jenna moaned as she reached out and took Neil's cock in her left hand slowly stroking it up and down. As Jenna slowly jerked off the playwright, Neil took his right hand off Jenna's breast and slid two of his fingers into Jenna's cooch. At the same time, Jenna played with Neil's balls gently massaging them in her hand before rubbing her open palm against the head of Neil's penis causing her hand to become covered in Neil's pre-cum which Jenna used to lather up Neil's penis as she returned to slowly stroking Neil's seven inch penis. Jenna could feel her orgasm building from everything that Neil was doing to her and when Neil slowly breathed onto her clit and licked it one more time, Jenna came all over Neil's fingers. "God you really know how to treat a girl," Jenna rasped in her post-orgasmic bliss, "but now it's time to make good on a promise." Neil gave Jenna a quick kiss on the lips and spun her over lining up his hard throbbing cock with Jenna's ass. "God I've been dreaming of this," Neil said as he slowly pushed himself into the actress. "Take it slowly at first but after I get used to your big cock, I want it really rough and hard," Jenna commanded with a smile. "You want it rough?" Neil repeated somewhat quizzically "Yes I want it fucking rough. I practiced with my husband last night and now I want it really hard and really fast. I want to be treated like the cheating slut I am," said Jenna with a sexy teasing smile knowing exactly what the playwright wanted to hear. Jenna got comfortable after a few minutes of Neil's cock invading her anal passageway and soon moaned, "pick up the pace honey. I want it really hard now." Jenna felt Neil's cock expand after her moaned lines and was feeling really good at the moment. "Oh fuck yes. This is so amazing," Neil shouted. "First time in a woman's ass, huh?" Jenna asked thoroughly enjoying her anal experience even more now that she knew she had the honor of having the first asshole that this cock had been in and which was giving her intense pleasure right at that moment. "Yes it fucking is. My wife is so damn plain in the bedroom. This is so much fun and it feels so fucking good," Neil cried moving one of his hands from holding Jenna's side and placing it on Jenna's pussy where he began to play with Jenna's clit. "That feels nice, keep doing that," Jenna breathlessly said. With that encouragement Neil rubbed Jenna's pussy faster and soon felt the cum begin to boil in his balls. "I'm gonna cum soon. Where do you want it?" Neil said as his relentless pointing drew him close to the point of no return. "Cum in my asshole. Fill me up you've earned it. Just hold off as long as you can, I want to cum with you," Jenna squealed as a big orgasm slowly began to build in her. "I can't hold it any longer," Neil groaned after a minute and his cum spewed into Jenna's waiting asshole. As his cum filled Jenna's ass, his right arm held Jenna close and his left hand continued to rub Jenna's slippery pussy. Jenna soon panted, "oh fuck I'm cumming again." And she did cum all over Neil's fingers again although this one was much more powerful than her first. Neil filled Jenna's ass with his cum and it came out of Jenna's ass with a loud plop as a long trail of his cum followed his cock out of Jenna's ass. They spooned each other for a few minutes carefully caressing and kissing each other before Jenna sighed, "I need to get home to my son and husband before they wonder where I am. See you tomorrow for opening night." "Can't wait til we can do this again," Neil replied as he moved to the side to let Jenna up. "Me too, stud, me too," Jenna answered as she got dressed, fixed her messy hair, and left. "Great job everyone!" Josh one of the play's actors and the guy Leslie had been flirting with earlier exclaimed as the curtain dropped signifying the end of the play's opening night. As the cast waited for the curtain to rise again to give a bow for the audience, Jenna thought she noticed Josh lightly playing with Leslie Bibb's rear end but she knew that Leslie had a huge smile on her face though. "I'll have to see what that's all about later," Jenna thought. After Jenna had signed autographs for the theater goers, she was still feeling great due to the high from the play and wanted to keep it going. It was then that she noticed Andrew whom she had picked up in a bar when she was previously in New York to audition for the play waiting for her with a bouquet of roses in his hands. "Are these lovely flowers for me?" asked Jenna. "Only the most beautiful flowers for the most wonderful woman," Andrew responded. "Oh I'll see if I can find Leslie around," Jenna joked and they both shared a laugh. "Why don't you stick around for a couple minutes and I'll give you the code to get into the back entrance," Jenna replied with a mischievous smile, "Let me go and make sure the dressing room is clear, I don't want anyone interrupting our fun and I have to share a dressing room with the other three actors in the play. So wait like fifteen minutes while I go get everything ready," Jenna said as she gave Andrew a quick peck on the check. Andrew waited while Jenna walked into her dressing room, she immediately noticed that Leslie was gone. "That's good," Jenna thought. "Let's hope that the boys are gone too." She walked over to the pocket door that divided the room between the girls and boys. She noticed the door was open slightly and when Jenna peaked around the corner, the sight she saw astounded her. There was Jenna's friend and costar Leslie Bibb on her knees sucking the cock of the play's lead actor, Josh. "I thought he was married and had a newborn baby. Oh wait, what the fuck does that matter, that describes me to a tee," Jenna thought. "Oh yea suck that cock baby," Josh pleaded. "I'm glad I could finally get this thing in my mouth," Leslie said between licks. "Well there's only so much a man can take of you and Jenna behaving like sexy rowdy sorority girls next door every single night," Josh panted. Jenna felt herself getting wet as she watched Leslie slowly blow the seven and a half inch cock that was dangling in front of her. "I want this monster in me," Leslie demanded before long. "Hope on," Josh responded pointing to his dick. Before long Leslie leaned back while still impaled on Josh's cock and whispered in her lover's hear, "Look over by the door." There was Jenna complete lost in her own world as she lay against the wall playing with herself. "Hey Jenna," Leslie shouted which bolted Jenna back to reality, "get your pretty little ass over here". "You like that don't you Josh?" Leslie asked as she felt his cock expand in her pussy, "You can't wait to have a threesome with me and Jenna." "Oh fuck yes," Josh enthusiastically said. "I thought you were married with a baby at home," Jenna said as she walked over and put two hands on Josh's naked chest while giving him a sexy kiss. "You and Leslie keep acting like dirty sorority girls every time we hang out in here together and Leslie's been quietly seducing me during all of our rehearsal scenes. A man whether married or not, with a new kid or not, can only hold out so long when two pretty girls want his cock. And once Leslie walked in her after the show tonight and dropped her skirt and took off her panties, it became impossible to resist. Besides aren't you married with a new born kid too," Josh said. "Yea but I've found out I'm just a slut for cock," Jenna responded as she removed her skirt leaving her in just her bra and panties. "I like the sound of that," Josh said as he resumed fucking Leslie's moist pussy. "And hopefully you'll be a slut for pussy specifically my pussy soon," Leslie sighed loving the pounding she was currently on the receiving end of, "Get over here, babe." Jenna moved over the Leslie and soon found herself deeply kissing a female for the first time in her life. It felt different than kissing a man not necessarily better but different. Leslie's lips were a lot softer than all the men she had been kissing lately and that seemed to make them more welcoming as well. Life After The Office Ch. 02 "I've never done it with a girl before," Jenna admitted to Leslie. "Well then you are in for a treat. First you're gonna eat me out then I'm going to eat you out and it's going to be the most wonderful thing you've ever felt in your life. Josh, I'm going to hop off this delectable cock of yours but don't worry because Jenna cheating pussy is going to hop right back on " Leslie told Jenna and Josh. "That sounds good," Josh and Jenna said in unison. Leslie got off Josh's cock and gave Jenna one last deep open-mouthed kiss with their tongues intertwining as their lips came together before Leslie positioned herself on a nearby sofa. Josh led Jenna over to the same sofa massaging her pussy on the way. "Wow you're really wet babe," Josh said. "This is really naughty and exciting. How can a girl not be wet?' Jenna responded as she placed her head between Leslie's legs and stuck out her backside in Josh's direction. "I know you've wanted this tight married pussy since we first met," Jenna cooed. "You're right babe but I was content with keeping that a fantasy. I never would've acted on it but you two ladies are so damn seductive," Josh answered as he lined his cock up with Jenna's waiting hole. "Well recently when I see something I want I take it. It doesn't matter if I'm cheating on my hubbie or not or if the guy or I guess now girl is married or not," Jenna moaned as Josh plunged his cock into Jenna's wet pussy. "Quit talking honey and start giving me an orgasm," Leslie said slightly perturbed. "Sorry babe," Jenna responded lowering her head into her new friend's pussy. Jenna spread Leslie's labia and and gently began to lick her pussy. "Oh fuck that's good, Jenna,' Leslie moaned. Jenna spread Leslie's little wet pussy apart and earnestly tasted Leslie's flowing juices. While she was doing this, Jenna also used one of her hands to massage Leslie's breasts while using her other fingers to rub Leslie's clit. She went slowly at first as if to tease Leslie but gradually picked up the pass as Jenna heard Leslie's breathing becoming more and more ragged. At the same time, Josh had sunk his whole cock in Jenna's cheating pussy. He had to go softly at first so Jenna could get accustomed to the new intruder in her hole but her pussy soon welcomed the strange dick invading it and enveloped itself around it pulling it deeper and deeper into her. Leslie soon neared orgasm between Jenna's skillful manipulation of her body. "You're making me cum Jenna. You may have never done this before but you're a fucking expert at it. Oh fuck," Leslie wailed as Jenna sucked down on her pussy and Leslie came all over Jenna's cute pretty face. Between the pounding Josh was giving her pussy and the satisfaction she was getting by bringing another woman to orgasm, Jenna was also approaching a mammoth orgasm of her own. And as Leslie exploded all over her face, Jenna knew she couldn't hold back any longer. "Oh shit, I'm fucking cumming too. Oh yea Josh, keep pounding my pussy while I cream your cock. Oh fuckkk," Jenna wailed and with one last thrust Josh held his cock in Jenna's orgasmic pussy. After Leslie came down from her high, she exclaimed, "oh shit, I have to meet my boyfriend Sam for dinner soon," she exclaimed quietly as she looked at the clock. "Make sure you each cum again for me," Leslie said as she gave Jenna a deep kiss on the mouth and made her tongue dance with Josh's as she got dressed and hurried out the door. Jenna then raised herself off the couch with Josh's still hard cock in her pussy and gave Josh a deep tonguing of her own and she took a few minutes to explore the married man's lips with hers. Jenna cooed as she felt Josh's cock expand in her pussy and she asked him what she wanted to do next. "Well my wife always says this is dirty and you can say no if you want to but I want to fuck you in the ass," Josh said matter-of-factly. With a smile Jenna said, "that's my specialty, just go slow until I get used to it." With one more kiss, Josh pulled out of Jenna's sopping pussy and aimed his cock for Jenna's asshole. As Josh was slowly working his hard cock into Jenna's ass, he heard Jenna moan, "hey babe, I thought you'd never get in here. He looked up to see a man that he had never seen before and hoped that it wasn't her husband. Jenna turned and looked at Josh, "Don't worry this is Andrew, he's a 'friend' of mine, so you can keep fucking my asshole. Andrew bring that big hard dick of yours over to me. Andrew walked over the couch where Josh had his right knee on one of the seats while he stood with his left leg and was gently fucking Jenna's asshole. Jenna herself had both knees on the couch and had glazed look in her eyes. Andrew stood in front of Jenna and lowered his head to lock his lips with the girl of his dreams for the second time. He continued to kiss her passionately while he took off his clothes. "hmm, I missed this big dick," Jenna grinned as she took Andrew's thick cock in her left hand and slowly began to stroke it with her wedding ring glistening with her sweat. She soon took it into her mouth and gave Andrew a nice wet blowjob, sucking on his cock while playing with his balls with her left hand and playing with her pussy with her right. "After I get this cock nice and erect, I want you to put it in my pussy and you two are going to fuck my ass and pussy at the same time. I've always wondered want double penetration would feel like and with two nice long cocks here, now's a good a time as any to try it," Jenna said as her ass had just started to get used to Josh's invading dick. Soon Andrew's cock was erect thanks to Jenna's amazing mouth and Andrew lay down on the couch with his dick in the air while the other two got in position. Jenna lay on top of Andrew and took his dick with her left hand and lined it up with her moist pussy. She gave Andrew a nice kiss as she moved it in and unexpectedly moaned into Andrew's mouth as Josh had moved behind Jenna and plunged his dick back into her ass. Jenna continued to moan as Andrew moved his right hand to Jenna's clit and slowly began to rub it while moving his left hand behind Jenna's head and softly pushing her lips even closer to his as they kissed even more passionately. Both Andrew and Josh went slowly at first as they had to get used to each fucking Jenna's pussy and ass respectively. But they picked up the pace as they got use to each other and soon Jenna raised her head and wailed, "Oh fuck yes this is fucking amazing, Keep fucking me and rubbing my clity. This is so fucking amazing. Oh fuckkk." Jenna screamed as she came all over Andrew's pistoning cock. "I'm cumming too babe, where do you want it," Josh called out as soon as he felt Jenna cumming. "Fill up my dirty asshole, you know you want to," Jenna demanded and that's exactly what Josh did. After Josh finished cumming he pulled his cock out of Jenna's gaping asshole and he too realized he had to get home to see his significant other. After he got dressed, he gave Jenna a nice kiss goodbye as she was now bouncing on Andrew's cock. As he left Jenna called out to him, "Josh make sure... hmm... you kiss your... hmmm... wife when you... hmmmm... get home with that... hmmmmm... dirty mouth of... hmmmmmm... yours," Jenna wailed as she again came on Andrew's dick. Josh could only smile as he went out the door. "Now where were we?' Jenna asked Andrew as she returned her attention to him. "How about you turn around and let me fuck you reverse cowgirl," Andrew responded to Jenna as she gently grinded on her lover's erect cock with her hands around his head. "That sounds like fun lover," Jenna said as she gave him a light kiss and slowly turned herself around. Jenna slowly lowered herself onto Andrew's engorged cock and moved lightly up and down at first so her pussy could get accustomed to the new position. After a few minutes she got used to it and began to move faster and harder and was soon slamming herself down on his cock while also furiously rubbing her clit. "Here let me do that," Andrew said as he removed Jenna's hand and put his on her clit, "a girl shouldn't have to rub herself while she's riding me as amazing as you fucking are." "Oh fuck yes I love when my men play with my pussy while they have their dick buried deep in me. It's so fucking hot,' Jenna moaned as she slammed herself down onto Andrew's cock as hard as she could go. When Andrew rubbed Jenna's clit as fast as he could, Jenna wailed, "oh fuck I'm going to cum all over your dick, I want you to cum with me." As soon as she finished saying this Jenna gripped onto the couch with both hands, leaned back, tensed up and shuddered as she exploded all over the cock in her pussy. At this moment Andrew exploded into the hot mom's pussy as Jenna shouted, "That's it cum in my married pussy with your big thick cock. Make me a cheating whore. Oh fuck yea." As they came down from their mutual orgasms Jenna put her left hand over his hand that was now slowly massaging her pussy to help him rub her. At that moment Andrew happened to look up and see their reflection in the dressing room mirror and he noticed the wedding ring on Jenna's hand that was helping him massage her clit and shot a little more cum into her pussy. "My husband never helps me get off, maybe that's why I have your dick in my pussy," Jenna looked back at Andrew with a smirk just before she put her right hand behind her lover's head and brought their mouth's together for one long french kiss to finish their fantastic fuck session. "I didn't even have this much sex in college" Jenna thought to herself, "and it certainly wasn't this crazy or intense. Yep my life couldn't be better."