My Boss, My Anal Slut Ch. 05-08

Chapter 5

"Oh, Dios mio ... fuck, yeah ... fuck me ... fuck me ... fuck my ASS, papi ... fuck my culo!" Angelica proved yet again how hooked she was on my sodomizing ways.

"You really do love this, don't you ... you're addicted to anal," I taunted her as I rode her, while Shawn impaled her with the utmost of his own vigor.

"God, yes ... I love it ... I love it ... I need it! I love it in both holes at once! It's my favorite thing ... to have both of you inside me at once! I know that we can't do this daily ... it's like ... dessert. A special treat now and then. Fuck ... yes!" Angelica creamed herself on Shawn's cock before clenching on him like a vise.

Shawn gasped as he spilled his seed inside Angelica's juicy twat, after which she squeezed my prick. I flooded her bowels as I admired her lovely buttocks. I cupped her cheeks while Shawn played with her tits for a bit. We all collapsed together and fell asleep. I must have slept at least three or four hours before I rose to hit the john. After washing my hands and sitting on a bar stool in the kitchen, I checked my voicemail and caught a message from Caroline, despite having warned her in a text just before eating the float that I wouldn't be home.

My call went through right away and Caroline answered it, "Damien, honey, is that you?"

"Yes, I got a voicemail to call you right away. I didn't see it until just now. I sent you a text earlier last night, telling you that I wouldn't make it home. I've been ... with my boss since getting off work. Well, with her and her fiance. Shawn, who also works with me. We kind of had to resolve some relationship issues ... and sealed our understanding with a few threesomes. The devil's kind, that is," I explained.

"Oh, sorry, I didn't have my cell phone on for a while and didn't check my texts before sending that voicemail, because I frankly didn't have the time. Damien, your mother was rushed to the hospital last night. James finally had enough of trying to handle her without help. It seems that his love for her finally overcame his religious convictions.

"Damien, she went into diabetic coma and hasn't come out of it. Her untreated diabetes might very well kill her and soon. I don't know if she will get out of it any time soon. The coma, that is. Damien, honey ... your mother's dying. She was no prize, not in my book, since she damn near let Alexis die. But she was still your mother. I wouldn't have you without her.

"In any case, I just barely turned on my phone when you called ... and yes, now I see the text. I guess that if we hadn't had this crisis, we would have been more worried about your absence, or else saw your text and found ways to divert ourselves. There is ... something else. Your father and I have talked. We ... discussed you. And our affair.

"I must confess that ... it was a set-up. Your father and I got together on this. The issue was how to ... satisfy me properly whenever your father was with Svetlana, since your father had to recover from his heart attack and couldn't use ... any potency medication. He doesn't have ED, of course, but he has limits. His testosterone levels are higher than normal for his age, but he is still an older man. You ... know ... middle-aged. And he's had one heart-attack, though actually sex helps with his heart and reduces the risk.

"Svetlana has been great in a number of ways. She has really put him on a diet and exercise plan that works for him ... including regular sex with me and her. They have grown really close, of course. But she also steered him away from patronizing bars as often as he once did, convinced him to drink less, eat less bar food, that kind of thing. Which has meant far less time bedding bar flies, you know.

"That being said, she's ... got him on those gym nights and that's at least two or three days a week. And she's a rather younger woman than I. I'm only ten years her senior, but those ten years are in some ways a lifetime. All well and good, but I need a man, too. Hence why ... you and I became an item. We both agreed that you'd be discreet, that you'd take care of me if something happened to him, and that if I got pregnant to you, it would be easier to handle.

"Hence the affair. The one between us. The point is that ... how do I put this delicately ... we would like you ... to ... for lack of a better word ... inherit me. Your mother's declining health just shows how rough things can be and how quickly things can go downhill. In the event that something bad should happen to him, we don't want to be caught off-guard.

"We ... came up with a plan. It's kinda crazy, but here it is. You can't marry your own former stepmother, of course. That would instantly raise suspicion. Should something happen to your father, Svetlana and I will tie the knot. He's discussed this with and we've all agreed on a lesbian wedding. That's fine with me, but she's not my main relationship and both of us know it. She and I have never even slept with each other ... at least not yet.

"Here's the deal. She would move in, yes, but you would become my main man. You'd also inherit her. Yes, that's right. You would bed both of us. And you would continue your own relationship with the girls ... you know, your sisters. Alexis and Daisy. And, of course, we would accept your ongoing workplace affair with your work wife aka your boss. Angelica, right?

"But we do need you to ... start sleeping with Svetlana sooner rather than later. Yes, you heard me right. You need to have an affair with your father's mistress as well as his wife. That way, she's already familiar and comfortable with you if and when your father should pass away. So, yeah, anyway, that's gonna hit you when you come home. Also, your father is now fully retired as of tomorrow. He's turned in his paperwork for his pension and for Social Security, too. Early retirement, you see.

"Any news from your side of things, babe?" Caroline inquired now.

"Yes, Angelica wanted me to tag along for a honeymoon cruise of hers, but that's rather sadly been ... postponed. Maybe it's for the best. Her fiance is set to begin training for the United States Secret Service, and evidently, that would be a schedule conflict, but it's an opportunity that he may never get again. Maybe ... just maybe, this delay happened for a reason," I said, my phone on speaker, "by the way, this phone's on speaker because Angelica might get up and I wouldn't want her to miss the chance to speak to you."

"It sounds ... almost providential, in fact. I was able to get credit that I can use again later, and maybe purchase extra reservations later. You must be Caroline, eh? The stepmother. Yeah, I was listening in on your convo this whole time. I'm Angelica, his boss ... and lover. Yes, I'm engaged to a great guy named Shawn. He's up, too, now. Say hi, Shawn, honey. This is my Damien's stepmother, who is also his lover," Angelica introduced Shawn as well as herself.

"Oh, hi, Angelica, Shawn. I'm ... Caroline. Would you like to speak to Bruce, Damien's father, too? And to Alexis and Daisy, his sisters? Technically, Daisy's his stepsister, but you wouldn't know it from how close they are. Oh, and here's Svetlana. She's crashing for the night, part of a little experiment. Say hello, guys!" Caroline announced herself and introduced the rest of my family.

"So, now ... worlds are colliding! Me and George Costanza!" I cracked that old Seinfeld joke.

"Oh, I don't think that you have an 'independent Damien,' dear. Just more than one 'relationship' version. You're like the bigamist whose wives have just met each other and decided to just get along. You caught a lucky break, babe," Angelica teased me now.

"Yeah, well, he didn't exactly lie to anyone, so that helps. He just compartmentalized and never let those worlds interact that much. Same thing with Bruce and his affair with Svetlana, except that I knew about that from the beginning. I approved of it, just as Shawn clearly approved of you and Damien. Just as you knew and approved of me. Just as Bruce knew and approved of Damien with me. Just as Bruce and I knew and also approved of his ongoing three-way relationship with Alexis and Daisy.

"So ... everyone's on the same page, right? Oh, and if and when something happens to Octavia, you're welcome to attend the funeral. It's likely to be hosted by James and follow the dogmas of the Christian Science quackery, but we'll have to just deal with that. He's a weird guy, but he loves her immensely. They treated her quickly, but fear some possible complications, since she still hasn't regained consciousness," Caroline explained now.

"Faith healing nearly killed Alexis. Now, it's killing Mom. Faith healing is murder," I declared, my mood much darker than hours earlier, while in the midst of a threesome with Angelica and Shawn.

"I love her ... I never stopped loving her, but I couldn't live with her and let her kill my children," Dad remarked, "that was what killed our marriage. And I still can't fully forgive her for putting Alexis in such danger. That's OUR DAUGHTER and she put religion over maternal instincts!"

"Excuse me ... there's a text from James," Alexis finally spoke, "yep ... guys. Mother ... just died. I'll never ... forgive her ... but she was my birth mother. She was never Mom to me. Caroline ... she's Mom to me. From day one."

"That's how I feel about Bruce ... he's ... Daddy," Daisy spoke, "sorry for your loss, Daddy ... Damien."

"Thank you ... I think that it's best if I go to bed ... and then on home in the morning. If that's okay with everyone. I'm in no condition to drive. Be sure to comfort each, girls ... and to comfort Dad," I said in a strained voice, "this ... this will take some ... adjustment. It's a sucker punch. One always held out hope of reconciliation, but it's never gonna happen now ... and I've got to try to sleep and make my peace with that ugly truth."

"Night ... nice to meet you guys. My condolences. Wish that things had been under easier circumstances," Angelica told my family.

"Very sorry for your loss. I will pray for her soul, for what it's worth," Shawn crossed himself, a sincere, if inconsistent and hypocritical Catholic.

"Amen," Caroline answered, being an Episcopalian herself, albeit lukewarm most of the time.

"Love you guys," I said as I hung up ... and burst into tears.

I somehow ended up in the master bed with Angelica and Shawn the former kissing me like a lover and the latter getting me some sleeping pills. I faded into dreams, uncertain of what to face. I just knew that I was luckier than James, who had no one to console him as a widower. I didn't care for the man, but we would all have to reach out to him and not leave the man alone.

Chapter 6

I awoke to Angelica riding me with her ass ... and she wasn't taking no for an answer. My hands were tied, too, much to my shock. What time was it, I wondered ... and why was I bound? Hell, I was gagged, too, I discovered as I tried to speak. She winked at me and kept riding me harder, taking me further up her butt. It was extremely intense and I worried that I might cum too fast for her, but I needn't have concerned myself too much.

I damn near passed out more than once as Angelica tightened up on me, using me both cowgirl-style and reverse-cowgirl. I tried to warn her, but she must have sensed it, anyway. I came in buckets up her culo, shooting rope after rope of accumulated jizz from my balls into her bowels. It was the most extreme release ever for me, made it even more invigorated when she wiped down my dick and stroked me before removing my gag.

"Shh ... just relax, papi. Sorry, but I had to assure everyone at work that you were a little 'tied-up' and couldn't make it in today. As you can see, I didn't lie, did I? My baby just lost his mother. I can't expect him to go to work and try to focus on the job, can I? Shawn's at work, it's just us for now, but we won't be alone for too much longer. I invited your sweet stepmother, sister, and stepsister over, for instance.

"Yes, I'm using some of your personal time, and applying it both today, tomorrow, and possibly the day after that. My being your boss comes in handy that way, wouldn't you say? Of course, I will work part of the day and such, but I will be here for the morning, going to work after lunch and surprising Shawn with ... well, you can guess. He thinks that I took the whole day off," my sultry supervisor stunned me, but this was hardly her last surprise for me.

Before I knew it, I heard voices coming closer from another room. Into my field of vision entered none other than my stepmother, Caroline, my sister, Alexis, and my stepsister, Daisy. My girls all kissed my flesh as Angelica joined them in bed with me, making me feel incredibly aroused from so much feminine attention. My skin never felt so alive, that much I knew. The ladies began sucking me in turns, even as Angelica waved her tits in my face to add to the excitement.

"I know that you're eager to be free from those bonds, and I promise that you'll be doing most of the tying up in our relationship. But today is about ... pampering you. We're all agreed on that. Alexis doesn't grieve Octavia's passing as you do. She was younger and didn't really view her as much as being her mother, not as you did for a critical time of your life. Caroline is her only real mother in every way that counts.

"Daisy, of course, doesn't know her all that well. She has no reason to grieve, either. But you, my dear, must have torn feelings. You need some ... catharsis, some way to release your pain and move forward. What better way to vent than through sexual healing, with apologies to Marvin Gaye, of course? You can indulge the flesh and enjoy the kisses, caresses, and bodies of your ladies today ... all of us," Angelica encouraged me, being part boss, part life coach, and part lover that morning.

"The wipe was so that you could fuck your stepmother's sweet pussy next. She really wants it now, don't you, dear?" Angelica declared, getting a nod from Caroline.

"Even more than usual. My sweet stepson needs comfort ... solace. He didn't get closure, but at least I can console him. Isn't that right, honey?" Caroline was even warmer and more ardent in her affections for me than she tended to be.

Given how loving my stepmother already was, that was saying a lot. Her long, wavy brown hair, her sleek, slender, graceful body, her small, but perky breasts, her lovely ass and hips that were perhaps a little wider than expected on such a slight frame ... those were all used to maximum effect on me. So were her soft, baby blue eyes and her wet lips which tasted faintly of pussy. Whose pussy, I didn't really care right then ... it was juicy and sweet, that was all I knew.

Then my stepsister, a plumper, slightly more tanned young lady with sandy hair, helped guide me into her mother's slippery snatch while my platinum blonde sister kissed my face repeatedly. Meanwhile, my sultry boss kissed my neck, shoulders, and chest. I wasn't sure where Daisy got her curvier body with a mother whose figure better resembled that of Alexis, but I was glad for each of them. I didn't mind the variety at all.

Of course, Alexis had started filling out since that nasty exchange with Mom and her firm decision to inquire about her lungs. It turned out that she had asthma that contributed to some chronic bronchitis, for which she was prescribed a fast-acting inhaler. She also got her yearly shot of pneumonia vaccine and that helped as well. Her only real health issues had been her lungs and the resulting thin physique that had slowed her development by a year or two.

"What's Dad doing, other than retiring today?" I asked once I had a moment to catch my breath and speak.

"He's spending part of the day with James, working out some details for the funeral and such. It turns out that the Christian Science faith doesn't really hold funerals in the formal sense. Of course, why would they? That would require some acknowledgement of grief and mourning, not to mention the reality of the body. He's setting up a funeral home for your mother with James. I think that she's going to be cremated, though, so that none of you guys have to look at her face in a casket.

"They hope to make it hurt less. We'll see. I think that the real issue is that Octavia never truly resolved her quarrels with anyone, since that would mean admitting that she was wrong about something. That just wasn't her style, baby. Anyway, the rest of the day will be spent in the loving arms of sweet Svetlana, enjoying her tender mercies. Well, that might be a misnomer, since she's not that merciful with her workout regimen. Word of warning, she's gonna likely try to rope us into it in time, including you," my sexy stepmom warned me as she rode me good and hard.

"Just so you know, breakfast is coming, and then we'll find ways to kill the time until you're hard again. Once you are, it's Daisy's turn, and then that of Alexis. I think that your sisters want to get pregnant by you ... and sooner rather than later. I can't say that I blame them. Part of me wouldn't mind if this first baby is yours. The other part still worries that Shawn would leave me if it was. If he ever does, I'll just move in with you. Try and stop me!" Angelica warned me.

"More fool him if he does. You're gonna be one helluva wife to him! And I don't think that he will leave you. I think that you two are perfect for each other. Not saying that he satisfies all of your needs, but no marriage or partner has to do that. That's why you have me. I'm just saying that he complements you well and vice versa. He's yin to your yang or something like that," I said while Caroline began really humping me with abandon.

"Yeah, I got him right where I want him. He's not gonna go. My only real worry is that pregnancy issue. But so far, he's content to assume that it's his, and he has a plausible reason to do so. After all, half of your spunk whenever we fuck tends to go in ... other holes. Less so with him. If anything, his favorite oral action is cunnilingus, though he's more open to rimming than he used to be. But yeah, that boy is ALL about the pussy!" Angelica relaxed a little more while parting my stepmother's cheeks to tongue her ass a little, "sorry, just got a little curious. I guess that means a hall pass for me from the box. I knew that was likely, though, so I stocked up on those hall passes."

"I can't blame either of you. Your pussy is delicious and so is Caroline's ass ... and yours, for that matter. You should try my stepmother's slit, too. You'd love it, if you enjoy her bottom so much. But yeah, I've seen how Shawn is about you. He has a very strong fondness for your gash. It's a pretty one, too, so he has great taste in it. It's a slick one as well. Very juicy, very wet. Though for my money, my favorite part of you remains your culo," I admitted freely, even as Daisy freed my left hand and Alexis my right, kissing my wrists afterward.

"No more bondage play for now. You've already told them that he's 'tied up' and he was ... for a little bit there. We just prefer his hands to be free, so we can do this to him," Alexis announced as she impaled her pussy with my right hand.

"My sentiments exactly," Daisy agreed while taking my fingers as far inside her own snatch as she could.

"Oh ... fuck, yeah ... God damn!" I cursed while Caroline rode me harder by the stroke.

Every last thrust of Caroline's hips, especially with Angelica's tongue lodged in her butt-crack, became more vigorous. Her breaths became more shallow by the second, her small, but lovely breasts heaving as she kissed my face repeatedly and bounced on my pole. My stepmother was sweet as peach cobbler, but at times like this she was downright wicked in the best sense of that term.

"Fuck me ... fuck me ... fuck me ... baby! Fill me up with your seed! Fucking breed me already! I'll tell you a little secret. Your father and I have a pact. I can deliberately get knocked up by you on the condition that he can intentionally put a baby in Svetlana. She needs an anchor baby and he wants to oblige her. My only price was getting to have your spawn inside me, a move that really doesn't bother him since you're family and would continue his line, his legacy," Caroline told me breathlessly, "and so I'm highly fertile right now. Probably just take one spurt or rope of your jizz to put a bun in my oven."