Sisterhood of Sin 13 The Cousin Who Isn t
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Sisterhood Of Sin -- 14 -- The Courage Jars free porn video
"Get naked now, you naughty boy!" My husband is already hard by the time he's finished undressing. I remain dressed in my business suit, but I made a point of letting him see that I was removing my panties as he came into the bedroom after coming home from work, and I deliberately wore sexy red panties to work that day.
"Over here. Hands on your knees." I like this position, me standing over him as he bends and waits for it. I land the single hard smack on the opposite ass cheek from the last time I gave him one of the spanks that I owed him.
"Sixteen!", he shouts. My hand stings a lot, but I think the pain helps to wake up my pussy. Seeing the bright pink hand print form on his white ass sure does. But this was the last spank that I owed him. Our weekday sex has gotten much better since I discovered this method of arousing us both, and since we knew this day would come, Dan had already lined up a replacement plan. He called it 'A Spank for a Spank'. Since I like to play the submissive role, too, we will alternate. Since I added one to the spanks he originally agreed to, he now owes me one, and he will order me to get naked while he stays clothed. He'll probably order me over his knee. And then will come the best part.
"Lick my cunt, slave." I sit in the straight-backed chair and spread my legs. As Dan fulfills my command, my hands roam into my blouse and pleasure my stiff nipples. I've become less reticent about coaching him as he licks me. "Down the hole. Now up. Faster. That's a good boy. Harder." I come as I hold his head against my crotch, smearing his face with the evidence of my lust."
I'm ready to please him now. "Take me. I'm yours." He impales me on his hard cock and shows off his strength, lifting me out of the chair and carrying me to the bed. Sometimes he orders me to ride him cowgirl style, but tonight it's missionary. I come again as he pummels me and then he comes, painting me white on the inside. He withdraws and I feel the wetness ooze into my ass crack and then down onto my half slip. Suddenly I smell the Chinese takeout that he brought home and I'm ravenous. "Let's eat."
I've told the tales about Dan, Celine, and Maritha, and the one night when their time together did so much to shape their futures apart, because the French Canadian Roman Catholic culture they sprang from, the culture I share with them, is both a culture of shame and a culture of interconnection. Family matters. Celine's comment about being owned and disowned was spot on. I emotionally disowned Dan after the second infidelity, even though we had the open marriage re-nup giving him permission for it. I've felt that loss since then. At times it hasn't been so bad. At other times it has been like a fresh open wound. We make a great team as co-habitators, but our sex life tends toward routine if I let it. Pretending that I own him long enough to drive us both wild with desire hasn't failed us yet. And now I will be letting him pretend to own me.
I think that I finally understand what went wrong with our sex life before I joined the sisterhood. The only sex we had was boring sex. It was loving sex, and that has its virtues, but there was nothing naughty about it. We were quiet, to keep the kids from hearing. We didn't do anything kinky, because we either weren't aware of the possibilities, or were just too inhibited to suggest them to each other. We didn't explore our dark sides. We didn't grow as sexual partners. We only grew as employees, the parents of our children, and postponers of gratification until the distant days of our 'Golden Years'. And now the sisterhood has both liberated us and damaged us further, well damaged me at least. But I have learned the rules that allow me to forgive myself. I can go to the edge, but no further, and have good sex. I only need to learn where the edge is.
Unfortunately, I think that I'm becoming addicted to Internet porn. When I think I'm safe from prying eyes, surf through images of men and women in chastity, or bound, or even wrapped in cling wrap with only their genitals exposed. I see them stimulated to the edge of orgasm and then denied the final push over that edge. Or sometimes I seen them hit with whips or canes.
I ask my shrink about my viewing habits, but she thinks it will pass as each of my quirks is 'rationalized', and she thinks I'm making great progress. The chronic masturbation has abated quite a bit. I still get inappropriate fantasies at inopportune times. I can be listening to any of my male coworkers during a business meeting and get a sudden disturbing image of him naked on the conference table with his cock caged and with two of my latex-gloved fingers in his ass or with his face buried in my pussy and his tongue licking Gabe's cum from it. One guy in particular has my attention. He's an arrogant prick who thinks he's God's gift to women, but I had no dominating carnal desires toward him until I heard office gossip that he is cheating on his wife with one of the younger women in Accounting. Now I visualize making him beg to be pegged with my strapon.
I alert Kyra about his cheating and she puts a team on it. They confirm the gossip and that his wife is a "good girl", a devoted mother who may think she has a happily-ever-after marriage. She looks like a good candidate for the sisterhood and we want to keep him employed with my company, so Kyra positions a 'friend' to monitor her and pick up the pieces if his wife detects his infidelity. If they were worth more to us, we might arrange to cause that detection, but so much can go wrong that we prefer not to intervene until she needs us.
But at least I've stopped sneaking into the ladies room at work and rubbin' my nubbin. My shrink has helped to alleviate much of the guilt I felt and she continues to encourage our special nights, which we've switched to Fridays. To keep from masturbating during the weekends, I wear my chastity belt except when I sleep or when Dan wants sex, or unless I have to go somewhere risky or meet someone.
I spend much of my weekend time either writing or enticing Dan away from his hobbies to molest me. We've had morning and afternoon sex and because he's getting enough and I'm holding off, he lasts longer and I come quicker. We've gone out to dinner at Pierre's, dressed elegantly, with me wearing my chastity belt under my dress and with his cock caged. We had really great sex that night.
Unfortunately, the Earn an Orgasm game quits working for us. We run out of new ways to try to get the other to remove their hardware. I tell my shrink that the chastity play has become routine and isn't naughty enough now. She suggests that I try a game that she calls 'the kink jars'. When she's done explaining it, I'm excited by the possibilities. I get a package of blank business card stock from a stationary store and begin writing every unusual sexual act and kink that I can think of, one per card, on them. She recommends that I even write the really sick stuff that I've heard about. "It's good to have stuff that you mutually agree to throw out."
I soon have a stack of kinks that is larger than expected. Per the shrink's suggestion, I don't use words like cunnilingus or fellatio. I write 'Pussy Licking' and 'Cock Sucking' on those cards, to make them seem more naughty. I separate the cards into two jars, one for situations where I will be the pleaser, and one for Dan to be the pleaser, to be alternated weekly, once we have trimmed the contents down by mutual agreement. Of course, chastity is on one of the cards in each jar, but each says 'Draw another card and add chastity'.
I present the concept to Dan and I call them 'courage jars' to challenge him to accept them. He agrees to contribute cards to both jars. After his initial reaction to the Earn an Orgasm game, I expected to hear, "Why are we doing this?", but he's either excited about the possibilities or resigned to letting me find ways to spice things up. Faun, his new mistress, has begun fucking him, so maybe his confidence is simply high enough that he doesn't mind doing whatever I want in the interest of keeping me happy. Whatever his reason, I'll take it. He also comes up with a larger than expected stack of cards. Many are duplicates of mine and as we go through them, some of each of our ideas move from one jar to the other.
By mutual agreement, many of the options are thrown out. Fortunately we both agree to throw out the really sick ones. Also by mutual agreement, some of the options are modified. Some have 'mock' or 'faux' qualifiers added to them, because we want to role play the scenarios without actually doing some of the deeds. For example, he wanted to throw out 'Cock and Ball Torture' but agreed that we could fake it if I wanted. I wanted to throw out 'Bondage', but changed it to 'Mock Bondage with Penalty' because I saw that as a way to stretch the boundaries in the way that the chastity devices did. One of those cards ended up in each jar.
Finally, we each had our jars. We took a few days to think about what we had left in the jars and what we had thrown out. Before our kinky date night, we had made additional changes. When 'Freaky Friday' finally arrives, Dan tosses a coin and I call 'tails'. It turns out to be prophetic, because he wins the toss, or loses it, depending on how one looks at it. He is the first to pull a card from his jar and submit to what it says.
I am very surprised that this particular card stayed in his jar at all. When he first read it, he thought about it for a long time as I waited. The card had said 'Pegging'. I expected to have to explain it to him, but he hadn't asked what it meant. Given his aversion to anything with other males and any sissification, I expected to be disappointed when he threw it away. Instead, he had modified it to, 'Sensual Pegging', and then I had to ask what that meant.
"It means I'm willing to do this, but I don't see myself as your 'bitch-boy'. I'll be passive for sensual anal lovemaking. I'm curious about my prostate and how it would feel to have it stimulated. It supposedly produces amazing orgasms. I also want to let you experience this, if you want, I just... want to show you that I support what you're doing here. This is naughty, and naughty can be fun."
His description could have ruined the fun for me. I had had visions of being very dominant and borderline abusive in fucking his ass with my strap-on. I had seen so many captioned photos of women dominating their cock-locked husbands with really big strapons and really rubbing in the humiliation they were dishing out. I had watched many short videos of huge dildos stretching men's asses. I had masturbated to fantasies of doing that to my husband.
But Dan was offering something else, something that could be good for him without being too negative to his self-image. When I thought about it, the power-transfer aspect that many women seemed to crave from pegging their husbands, had already happened when I forced him into the re-nup agreement. I had won the option of cuckolding him and now I wanted to go much further beyond humiliation with him. Why was I fantasizing about becoming like Mrs. Fuscia, a woman I despised? I had been telling myself that I wanted to find out what kind of man Dan is. I had been thinking along alpha or beta male lines, but my shrink has warned me that those are silly ways to pigeonhole complex creatures. In her words, "Those are fine for stupid, simple men, but it sounds like Dan is smart and complex. He was raised within the same abusive culture you were. You should allow him to be a 'switch', just like you are. And even that is too simple to describe you both."
So I had warmed to the idea of 'making love' to Dan's ass in the same way that I would use my strap-on to make love to Kyra or Claire. We had left the card as Dan had modified it, and I am happy that it is the first card that Dan drew. Dan does not look so happy. The future of 'Freaky Friday' hinges on how this plays out and he looks very uncomfortable and anxious. In terms of submission, this is way beyond a short chastity session. It is potentially very humiliating. I have to play this carefully, to choose correctly between Cate Confidence and Sister Cate. I choose Cate Confidence. Maybe I can graduate him to Sister Cate the next time this card comes up.
"Sir, I promise I will make this as good as I can for you. I want you to enjoy this. I'm willing to do whatever it takes to make it enjoyable. I can help you prepare. I can wear whatever you want me to wear. I can do whatever you want. You can have as much control as you want."
"Do you even have the uh... necessary equipment?"
"Yes, Sir. I've never done this with a man, but I have what it takes."
I want him to have a mental image of me fucking a woman with a faux cock.
"I want to make sure that it isn't too big."
"Certainly, Sir."
I bring him my strap-on and put it in his hands. He sees that I did not supersize it when I bought it. The dildo is about the same size as his erect cock. My plan is to point out the similarity if he claims it is too big, but he doesn't seem alarmed by it. He also sees that my end of it will penetrate both my pussy and my ass while I'm wearing it.
"Where did you get this. I've never seen one like it."
"One of the sisters is very creative. She works with metal, wood, plastic, latex, leather, and glass. She also made my chastity belt."
He wraps his fingers around the post that goes in my ass. "So you will need to prepare, too?"
"Yes."
I don't like to talk about the cleansing steps, but of course we both go through them. I think that helps ease his anxiety, because we both laugh nervously as we prepare. When we return to the bedroom, I give him a tube of lubricant.
"Sir, would you like the honor of fitting this into me?"
"Sure."
By doing this, I let him penetrate me with the posts that I use to grip and hold my cock. It seems to ease some of his anxiety. He lubricates the anal post and gently pushes it in. The other post slips easily into my pussy, lubricated with my natural juice. I use my anal and vaginal muscles to make my cock move without moving my hips. He seems fascinated by it. I decide not to clip the metal balls on, this time. I don't want to seem too masculine. As he ties the straps behind me, he says, "You're already very wet. You're enjoying this."
"Yes, but I'm also very nervous. I don't want to abuse your generosity."
"That's a good name for it. My 'generosity'. I'll probably think of this in my ass whenever somebody says generosity in the future. I hope I don't regret it."
"I won't give you reason to. I think it is an honor, Sir. Now, do you want me to wear any special clothing?"
We're both completely naked and his cock is limp. The difference in size between our cocks makes up for the advantage he has in height and I do feel what Kyra's husband referred to as 'the power of the cock'.
"No, Cathy, and you don't need to call me 'Sir'. I think I would like to make love to my wife tonight."
That is such a sweet thing to say that I almost forget that he's the man who sent us both on this strange journey by screwing the babysitter. "Thank you, Dan. That makes me feel so... loved. What position do you think will work best?"
"I think you need to be poking your uh... forward toward my prostate. How about we try laying on our sides with you spooning behind me."
It's not the position I wanted to try. It's really not a position of superiority, dominance, or power. But it is good. After using a lubed finger to relax his tight hole, I smear some gel on the dildo and succeed in penetrating him. He squirms around a little to position my thrusts so they push toward his prostate at the base of his cock. I give him a 'reacharound' stroking his cock slowly with my hand as I slowly thrust into him. When he gets hard, he removes my hand from his cock.
"Let's try it without that. Just keep going like you are."
I move my hand up to his nipple instead, circling it slowly with just a fingertip. He has said that playing with his nipples does nothing for him, but I'm not so sure. It's certainly doing something for me. I'm giving his ass short strokes, slowly getting faster and faster as he moans. I listen and use his sounds to help me take him to the edge. I keep him there, for a while by slowing and lengthening my strokes, letting his desire build and hoping mine will. When it seems right, I increase the speed and force of my strokes and he comes, spraying it out onto the towel he positioned there, with nothing touching his cock.
"That was... intense. Did you come, Cathy?"
"Um, no. It's okay though."
"Can you come from using that?"
"Yes, in the right position."
"What would that be?"
"Um, doggy works best. But that's okay. You don't have to."
"Do it. It's okay. I can tell you want to."
I pull my cock out of him and he gets up onto elbows and knees. Getting behind him, I put more lube on my dildo and push it back into him. For a short time, I just stop and look down at his ass with my cock buried deep in it. I've obviously seen women, both their front and back sides, as I've fucked them with my dildo, but this seems so much naughtier.
"Go ahead, Cathy. It's not so bad. I can take it."
I place my hands on his hips and start ramming, long strokes that end with my thighs connecting hard enough to rock him forward. I clench my pussy and ass muscles around the posts of my dildo and that makes it rub my clit just the right amount. I start thinking a stream of obscenities that I dare not say.
'Take my cock in your boy-cunt you little butt-whore. You fucking ass-slut, you're my bitch now.' I don't know where these thoughts are coming from, but as I look down and watch my cock stretching his pink, gaping hole, I start slapping his ass with my hands and I come. I imagine myself pumping cum into him as my muscles clench and relax around the posts of my dildo. I ram his ass until I'm spent and then pull my cock out and collapse on the bed. My cock is pointing straight up, wobbling around, but unlike Dan's, staying hard.
Dan flips onto his back. He's breathing almost as hard as I am. He looks over at me and smiles. "You really got into that."
"Yup. Sorry. I guess I got a little carried away. Not very sensual."
"That's okay. The first part was very good for me. And I could tell that the second part was important to you."
"Yup. You know how I am about inequality. Sometimes I like to feel inferior and it's good that you let me balance that out by playing the superior role. I guess I've felt unequal ever since I let you fuck my ass. Now we're equal. I think my ass will be more receptive in the future, like, as soon as you're ready again."
"Really?"
The look of eagerness on his face is almost comical. I had planned in advance on rewarding him with anal sex, to soothe any bruised ego. It's easy to be generous with something I want anyway, to feel irresistible. I nod my head.
"I know what you mean about inferior and superior. Giving pleasure and taking pleasure. I like both Sister Cate and Cate the pleaser. Maybe we could incorporate that into the jars."
"I don't know, Dan. Do you think you could handle Sister Cate wearing one of these?"
"I would do it to please you, Cathy."
It isn't an answer I expected. He would submit to Sister Cate to please me, not to please himself, or at least he isn't admitting it would be to please himself. But I'll take what I can get. First I need to consolidate my gain.
"That's so sweet. I think Sister Cate would like that. She might say some nasty things to you, but I won't really mean them. They're just part of the role play. But for now, Sir. Please help me out of this rig, so I can please you again."
I think it was a good decision to go with Cate Confidence this time. We take a break and have a drink. When Dan gets hard, he lubes his cock and buries it in my ass, but he doesn't start fucking me right away. I'm on my knees on the bed, almost upright with my hands on the top of the headboard, leaning a little of my weight forward on my arms. Dan nuzzles his nose into my hair, nibbles my ear, and kisses and gently bites my shoulder. I'm getting almost no stimulation of my pussy, nothing on my clit, and I soon find myself amazingly close to coming. I'm not getting all the way there, but when he starts to caress my nipples with a double reacharound and then drops one hand down to cup my pussy, I cross that gap and start to come. His fingers find my clit and his cock starts with very short thrusts, slowly increasing until he's almost pulling out with each stroke, but not going faster. I'm coming almost the whole time, a different kind of orgasm, short periods of low intensity between longer highly intense periods of orgasmic bliss. Multi-coming. It's extremely satisfying and I want it to last forever.
Dan starts to come and a deep rumbling growl comes from him. He's pumping his hot cum into my ass, feeling the squeezing of my tight muscle milking his cock as it slowly strokes in and out. When it shrinks and pops out, I can feel my anus still pulsing, but it soon closes. I put my hand over his and help him give me a few more strokes on my clit before lifting it away.
"That was amazing, Dan."
"Did you come?" For some reason, I did not make much sound while he fucked me so perfectly. Maybe focusing on the exquisite sensations from the slow stokes and the multiple locations turned my vocal cords off. I know I gasped and had my mouth open a lot.
"Yup. It was... I can't describe it. It was very special and I hope it happens again. I want more of this." I silently vow to try this upright slow fuck technique on him the next time the Sensual Pegging card comes up.
"Over here. Hands on your knees." I like this position, me standing over him as he bends and waits for it. I land the single hard smack on the opposite ass cheek from the last time I gave him one of the spanks that I owed him.
"Sixteen!", he shouts. My hand stings a lot, but I think the pain helps to wake up my pussy. Seeing the bright pink hand print form on his white ass sure does. But this was the last spank that I owed him. Our weekday sex has gotten much better since I discovered this method of arousing us both, and since we knew this day would come, Dan had already lined up a replacement plan. He called it 'A Spank for a Spank'. Since I like to play the submissive role, too, we will alternate. Since I added one to the spanks he originally agreed to, he now owes me one, and he will order me to get naked while he stays clothed. He'll probably order me over his knee. And then will come the best part.
"Lick my cunt, slave." I sit in the straight-backed chair and spread my legs. As Dan fulfills my command, my hands roam into my blouse and pleasure my stiff nipples. I've become less reticent about coaching him as he licks me. "Down the hole. Now up. Faster. That's a good boy. Harder." I come as I hold his head against my crotch, smearing his face with the evidence of my lust."
I'm ready to please him now. "Take me. I'm yours." He impales me on his hard cock and shows off his strength, lifting me out of the chair and carrying me to the bed. Sometimes he orders me to ride him cowgirl style, but tonight it's missionary. I come again as he pummels me and then he comes, painting me white on the inside. He withdraws and I feel the wetness ooze into my ass crack and then down onto my half slip. Suddenly I smell the Chinese takeout that he brought home and I'm ravenous. "Let's eat."
I've told the tales about Dan, Celine, and Maritha, and the one night when their time together did so much to shape their futures apart, because the French Canadian Roman Catholic culture they sprang from, the culture I share with them, is both a culture of shame and a culture of interconnection. Family matters. Celine's comment about being owned and disowned was spot on. I emotionally disowned Dan after the second infidelity, even though we had the open marriage re-nup giving him permission for it. I've felt that loss since then. At times it hasn't been so bad. At other times it has been like a fresh open wound. We make a great team as co-habitators, but our sex life tends toward routine if I let it. Pretending that I own him long enough to drive us both wild with desire hasn't failed us yet. And now I will be letting him pretend to own me.
I think that I finally understand what went wrong with our sex life before I joined the sisterhood. The only sex we had was boring sex. It was loving sex, and that has its virtues, but there was nothing naughty about it. We were quiet, to keep the kids from hearing. We didn't do anything kinky, because we either weren't aware of the possibilities, or were just too inhibited to suggest them to each other. We didn't explore our dark sides. We didn't grow as sexual partners. We only grew as employees, the parents of our children, and postponers of gratification until the distant days of our 'Golden Years'. And now the sisterhood has both liberated us and damaged us further, well damaged me at least. But I have learned the rules that allow me to forgive myself. I can go to the edge, but no further, and have good sex. I only need to learn where the edge is.
Unfortunately, I think that I'm becoming addicted to Internet porn. When I think I'm safe from prying eyes, surf through images of men and women in chastity, or bound, or even wrapped in cling wrap with only their genitals exposed. I see them stimulated to the edge of orgasm and then denied the final push over that edge. Or sometimes I seen them hit with whips or canes.
I ask my shrink about my viewing habits, but she thinks it will pass as each of my quirks is 'rationalized', and she thinks I'm making great progress. The chronic masturbation has abated quite a bit. I still get inappropriate fantasies at inopportune times. I can be listening to any of my male coworkers during a business meeting and get a sudden disturbing image of him naked on the conference table with his cock caged and with two of my latex-gloved fingers in his ass or with his face buried in my pussy and his tongue licking Gabe's cum from it. One guy in particular has my attention. He's an arrogant prick who thinks he's God's gift to women, but I had no dominating carnal desires toward him until I heard office gossip that he is cheating on his wife with one of the younger women in Accounting. Now I visualize making him beg to be pegged with my strapon.
I alert Kyra about his cheating and she puts a team on it. They confirm the gossip and that his wife is a "good girl", a devoted mother who may think she has a happily-ever-after marriage. She looks like a good candidate for the sisterhood and we want to keep him employed with my company, so Kyra positions a 'friend' to monitor her and pick up the pieces if his wife detects his infidelity. If they were worth more to us, we might arrange to cause that detection, but so much can go wrong that we prefer not to intervene until she needs us.
But at least I've stopped sneaking into the ladies room at work and rubbin' my nubbin. My shrink has helped to alleviate much of the guilt I felt and she continues to encourage our special nights, which we've switched to Fridays. To keep from masturbating during the weekends, I wear my chastity belt except when I sleep or when Dan wants sex, or unless I have to go somewhere risky or meet someone.
I spend much of my weekend time either writing or enticing Dan away from his hobbies to molest me. We've had morning and afternoon sex and because he's getting enough and I'm holding off, he lasts longer and I come quicker. We've gone out to dinner at Pierre's, dressed elegantly, with me wearing my chastity belt under my dress and with his cock caged. We had really great sex that night.
Unfortunately, the Earn an Orgasm game quits working for us. We run out of new ways to try to get the other to remove their hardware. I tell my shrink that the chastity play has become routine and isn't naughty enough now. She suggests that I try a game that she calls 'the kink jars'. When she's done explaining it, I'm excited by the possibilities. I get a package of blank business card stock from a stationary store and begin writing every unusual sexual act and kink that I can think of, one per card, on them. She recommends that I even write the really sick stuff that I've heard about. "It's good to have stuff that you mutually agree to throw out."
I soon have a stack of kinks that is larger than expected. Per the shrink's suggestion, I don't use words like cunnilingus or fellatio. I write 'Pussy Licking' and 'Cock Sucking' on those cards, to make them seem more naughty. I separate the cards into two jars, one for situations where I will be the pleaser, and one for Dan to be the pleaser, to be alternated weekly, once we have trimmed the contents down by mutual agreement. Of course, chastity is on one of the cards in each jar, but each says 'Draw another card and add chastity'.
I present the concept to Dan and I call them 'courage jars' to challenge him to accept them. He agrees to contribute cards to both jars. After his initial reaction to the Earn an Orgasm game, I expected to hear, "Why are we doing this?", but he's either excited about the possibilities or resigned to letting me find ways to spice things up. Faun, his new mistress, has begun fucking him, so maybe his confidence is simply high enough that he doesn't mind doing whatever I want in the interest of keeping me happy. Whatever his reason, I'll take it. He also comes up with a larger than expected stack of cards. Many are duplicates of mine and as we go through them, some of each of our ideas move from one jar to the other.
By mutual agreement, many of the options are thrown out. Fortunately we both agree to throw out the really sick ones. Also by mutual agreement, some of the options are modified. Some have 'mock' or 'faux' qualifiers added to them, because we want to role play the scenarios without actually doing some of the deeds. For example, he wanted to throw out 'Cock and Ball Torture' but agreed that we could fake it if I wanted. I wanted to throw out 'Bondage', but changed it to 'Mock Bondage with Penalty' because I saw that as a way to stretch the boundaries in the way that the chastity devices did. One of those cards ended up in each jar.
Finally, we each had our jars. We took a few days to think about what we had left in the jars and what we had thrown out. Before our kinky date night, we had made additional changes. When 'Freaky Friday' finally arrives, Dan tosses a coin and I call 'tails'. It turns out to be prophetic, because he wins the toss, or loses it, depending on how one looks at it. He is the first to pull a card from his jar and submit to what it says.
I am very surprised that this particular card stayed in his jar at all. When he first read it, he thought about it for a long time as I waited. The card had said 'Pegging'. I expected to have to explain it to him, but he hadn't asked what it meant. Given his aversion to anything with other males and any sissification, I expected to be disappointed when he threw it away. Instead, he had modified it to, 'Sensual Pegging', and then I had to ask what that meant.
"It means I'm willing to do this, but I don't see myself as your 'bitch-boy'. I'll be passive for sensual anal lovemaking. I'm curious about my prostate and how it would feel to have it stimulated. It supposedly produces amazing orgasms. I also want to let you experience this, if you want, I just... want to show you that I support what you're doing here. This is naughty, and naughty can be fun."
His description could have ruined the fun for me. I had had visions of being very dominant and borderline abusive in fucking his ass with my strap-on. I had seen so many captioned photos of women dominating their cock-locked husbands with really big strapons and really rubbing in the humiliation they were dishing out. I had watched many short videos of huge dildos stretching men's asses. I had masturbated to fantasies of doing that to my husband.
But Dan was offering something else, something that could be good for him without being too negative to his self-image. When I thought about it, the power-transfer aspect that many women seemed to crave from pegging their husbands, had already happened when I forced him into the re-nup agreement. I had won the option of cuckolding him and now I wanted to go much further beyond humiliation with him. Why was I fantasizing about becoming like Mrs. Fuscia, a woman I despised? I had been telling myself that I wanted to find out what kind of man Dan is. I had been thinking along alpha or beta male lines, but my shrink has warned me that those are silly ways to pigeonhole complex creatures. In her words, "Those are fine for stupid, simple men, but it sounds like Dan is smart and complex. He was raised within the same abusive culture you were. You should allow him to be a 'switch', just like you are. And even that is too simple to describe you both."
So I had warmed to the idea of 'making love' to Dan's ass in the same way that I would use my strap-on to make love to Kyra or Claire. We had left the card as Dan had modified it, and I am happy that it is the first card that Dan drew. Dan does not look so happy. The future of 'Freaky Friday' hinges on how this plays out and he looks very uncomfortable and anxious. In terms of submission, this is way beyond a short chastity session. It is potentially very humiliating. I have to play this carefully, to choose correctly between Cate Confidence and Sister Cate. I choose Cate Confidence. Maybe I can graduate him to Sister Cate the next time this card comes up.
"Sir, I promise I will make this as good as I can for you. I want you to enjoy this. I'm willing to do whatever it takes to make it enjoyable. I can help you prepare. I can wear whatever you want me to wear. I can do whatever you want. You can have as much control as you want."
"Do you even have the uh... necessary equipment?"
"Yes, Sir. I've never done this with a man, but I have what it takes."
I want him to have a mental image of me fucking a woman with a faux cock.
"I want to make sure that it isn't too big."
"Certainly, Sir."
I bring him my strap-on and put it in his hands. He sees that I did not supersize it when I bought it. The dildo is about the same size as his erect cock. My plan is to point out the similarity if he claims it is too big, but he doesn't seem alarmed by it. He also sees that my end of it will penetrate both my pussy and my ass while I'm wearing it.
"Where did you get this. I've never seen one like it."
"One of the sisters is very creative. She works with metal, wood, plastic, latex, leather, and glass. She also made my chastity belt."
He wraps his fingers around the post that goes in my ass. "So you will need to prepare, too?"
"Yes."
I don't like to talk about the cleansing steps, but of course we both go through them. I think that helps ease his anxiety, because we both laugh nervously as we prepare. When we return to the bedroom, I give him a tube of lubricant.
"Sir, would you like the honor of fitting this into me?"
"Sure."
By doing this, I let him penetrate me with the posts that I use to grip and hold my cock. It seems to ease some of his anxiety. He lubricates the anal post and gently pushes it in. The other post slips easily into my pussy, lubricated with my natural juice. I use my anal and vaginal muscles to make my cock move without moving my hips. He seems fascinated by it. I decide not to clip the metal balls on, this time. I don't want to seem too masculine. As he ties the straps behind me, he says, "You're already very wet. You're enjoying this."
"Yes, but I'm also very nervous. I don't want to abuse your generosity."
"That's a good name for it. My 'generosity'. I'll probably think of this in my ass whenever somebody says generosity in the future. I hope I don't regret it."
"I won't give you reason to. I think it is an honor, Sir. Now, do you want me to wear any special clothing?"
We're both completely naked and his cock is limp. The difference in size between our cocks makes up for the advantage he has in height and I do feel what Kyra's husband referred to as 'the power of the cock'.
"No, Cathy, and you don't need to call me 'Sir'. I think I would like to make love to my wife tonight."
That is such a sweet thing to say that I almost forget that he's the man who sent us both on this strange journey by screwing the babysitter. "Thank you, Dan. That makes me feel so... loved. What position do you think will work best?"
"I think you need to be poking your uh... forward toward my prostate. How about we try laying on our sides with you spooning behind me."
It's not the position I wanted to try. It's really not a position of superiority, dominance, or power. But it is good. After using a lubed finger to relax his tight hole, I smear some gel on the dildo and succeed in penetrating him. He squirms around a little to position my thrusts so they push toward his prostate at the base of his cock. I give him a 'reacharound' stroking his cock slowly with my hand as I slowly thrust into him. When he gets hard, he removes my hand from his cock.
"Let's try it without that. Just keep going like you are."
I move my hand up to his nipple instead, circling it slowly with just a fingertip. He has said that playing with his nipples does nothing for him, but I'm not so sure. It's certainly doing something for me. I'm giving his ass short strokes, slowly getting faster and faster as he moans. I listen and use his sounds to help me take him to the edge. I keep him there, for a while by slowing and lengthening my strokes, letting his desire build and hoping mine will. When it seems right, I increase the speed and force of my strokes and he comes, spraying it out onto the towel he positioned there, with nothing touching his cock.
"That was... intense. Did you come, Cathy?"
"Um, no. It's okay though."
"Can you come from using that?"
"Yes, in the right position."
"What would that be?"
"Um, doggy works best. But that's okay. You don't have to."
"Do it. It's okay. I can tell you want to."
I pull my cock out of him and he gets up onto elbows and knees. Getting behind him, I put more lube on my dildo and push it back into him. For a short time, I just stop and look down at his ass with my cock buried deep in it. I've obviously seen women, both their front and back sides, as I've fucked them with my dildo, but this seems so much naughtier.
"Go ahead, Cathy. It's not so bad. I can take it."
I place my hands on his hips and start ramming, long strokes that end with my thighs connecting hard enough to rock him forward. I clench my pussy and ass muscles around the posts of my dildo and that makes it rub my clit just the right amount. I start thinking a stream of obscenities that I dare not say.
'Take my cock in your boy-cunt you little butt-whore. You fucking ass-slut, you're my bitch now.' I don't know where these thoughts are coming from, but as I look down and watch my cock stretching his pink, gaping hole, I start slapping his ass with my hands and I come. I imagine myself pumping cum into him as my muscles clench and relax around the posts of my dildo. I ram his ass until I'm spent and then pull my cock out and collapse on the bed. My cock is pointing straight up, wobbling around, but unlike Dan's, staying hard.
Dan flips onto his back. He's breathing almost as hard as I am. He looks over at me and smiles. "You really got into that."
"Yup. Sorry. I guess I got a little carried away. Not very sensual."
"That's okay. The first part was very good for me. And I could tell that the second part was important to you."
"Yup. You know how I am about inequality. Sometimes I like to feel inferior and it's good that you let me balance that out by playing the superior role. I guess I've felt unequal ever since I let you fuck my ass. Now we're equal. I think my ass will be more receptive in the future, like, as soon as you're ready again."
"Really?"
The look of eagerness on his face is almost comical. I had planned in advance on rewarding him with anal sex, to soothe any bruised ego. It's easy to be generous with something I want anyway, to feel irresistible. I nod my head.
"I know what you mean about inferior and superior. Giving pleasure and taking pleasure. I like both Sister Cate and Cate the pleaser. Maybe we could incorporate that into the jars."
"I don't know, Dan. Do you think you could handle Sister Cate wearing one of these?"
"I would do it to please you, Cathy."
It isn't an answer I expected. He would submit to Sister Cate to please me, not to please himself, or at least he isn't admitting it would be to please himself. But I'll take what I can get. First I need to consolidate my gain.
"That's so sweet. I think Sister Cate would like that. She might say some nasty things to you, but I won't really mean them. They're just part of the role play. But for now, Sir. Please help me out of this rig, so I can please you again."
I think it was a good decision to go with Cate Confidence this time. We take a break and have a drink. When Dan gets hard, he lubes his cock and buries it in my ass, but he doesn't start fucking me right away. I'm on my knees on the bed, almost upright with my hands on the top of the headboard, leaning a little of my weight forward on my arms. Dan nuzzles his nose into my hair, nibbles my ear, and kisses and gently bites my shoulder. I'm getting almost no stimulation of my pussy, nothing on my clit, and I soon find myself amazingly close to coming. I'm not getting all the way there, but when he starts to caress my nipples with a double reacharound and then drops one hand down to cup my pussy, I cross that gap and start to come. His fingers find my clit and his cock starts with very short thrusts, slowly increasing until he's almost pulling out with each stroke, but not going faster. I'm coming almost the whole time, a different kind of orgasm, short periods of low intensity between longer highly intense periods of orgasmic bliss. Multi-coming. It's extremely satisfying and I want it to last forever.
Dan starts to come and a deep rumbling growl comes from him. He's pumping his hot cum into my ass, feeling the squeezing of my tight muscle milking his cock as it slowly strokes in and out. When it shrinks and pops out, I can feel my anus still pulsing, but it soon closes. I put my hand over his and help him give me a few more strokes on my clit before lifting it away.
"That was amazing, Dan."
"Did you come?" For some reason, I did not make much sound while he fucked me so perfectly. Maybe focusing on the exquisite sensations from the slow stokes and the multiple locations turned my vocal cords off. I know I gasped and had my mouth open a lot.
"Yup. It was... I can't describe it. It was very special and I hope it happens again. I want more of this." I silently vow to try this upright slow fuck technique on him the next time the Sensual Pegging card comes up.
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