30 Days: Nov. 16th (Patreon)

As I ponder over what might be within the unopened envelope in my hand I reflect again on the events of yesterday.

It killed me to admit it, but I was enjoying this. On some level this was striking some deep unfulfilled need inside of me. It was a need I neither wanted nor wished to encourage, but it was there whether I liked it or not. In the madness that seized me I had cum so fucking hard and so fast imagining Sarah bent over and taking her big dildo to the balls that it was impossible to deny that something was going on.

Unlike the first time though one breaking of my chastity challenge hadn’t been enough. As I stewed on it afterward I found myself obsessing over the owner of the big cock that had reamed my wife’s pussy. The more I focused on it the more my manly pride demanded that I do something, anything, to reclaim my place as the man of the house. For some fucked up reason what those thoughts eventually turned into was me watching that damned porn video of the older stud fucking the maid again. With my hand lubed up and his replica phallus laying in front of me I once more tried to go stroke for stroke with the man in some vain effort to outlast him. As I masturbated all I could see is my wife as the maid he was ravishing. The second round against him didn’t go much better for me as I was busting ball butter not even halfway through the scene. And god damn if this nut wasn’t just as good as the earlier one. Not only was it just as powerful but as I watched them carry on fucking with no signs of stopping, his stamina besting me even more than his impressive size, my orgasm seemed to draw out extra long as well.

I was beginning to worry. A hotwife kink was one thing but this seemed like something more. Was I a cuckold?

I decide that I wasn’t. Or at the very least I wouldn’t let it get that far. Not for real. No way. Dad didn’t raise no cuck! Dildos and stories and movies and even some risque flirting would be fantasy enough for me, and for Sarah. Fantasies we could explore together within the sanctity of our vows. Nobody had really seen her yet or touched her yet or done anything with her yet. As her husband her body was still mine to enjoy and nobody else’s.

Deep down I still held the faith that Sarah would know where to draw the line on her own and I wanted to give her the chance to get there herself. I did not want to stifle her or control her and I still was curious as to just how close to the line she would get. But whether it was her or I the time to call it quits was very close now. Probably today or maybe tomorrow or the next day, it would depend on what was in this letter.

As I tore the envelope open I wondered if she had figured out that I had broken my NNN challenge again. I’d been more careful this time not to act any differently. It turned out that it wasn’t so hard to act frustrated and ready to burst. Whenever I looked to my sweet, beautiful, blond haired, blue eyed wife all I had do is imagine her taking that porn star’s thick 8 inch cock up her tight cunny and I felt plenty pent up.

***

Dear David,

Well, I think last night did wonders for work morale! Ha ha ha! Talk about a team building exercise!

After giving my hard working man a kiss goodbye I was soon out the door myself. Tonia and James had invited me to their place for a little after work get together. I’ve found out that they have these quite regularly but I’d never been invited before because they are only for the ‘cool’ guys and gals. I feel like I’m suddenly part of some super secret club or something! I didn’t exactly know what to expect. I knew this wasn’t a normal social gathering but the details were left vague. Tonia assured me that I wouldn’t be pressured into anything and that there were no expectations. I simply had to show up with an open mind.

I was a bundle of nerves when I arrived. I was both excited and apprehensive. Color me surprised when I showed up to see Casey and Maria, one of our volunteer mom’s, already there. With Maria I was stunned because she had always seemed like such a traditional, wholesome, conservative kind of woman. I never expected her to be ‘cool’. Turns out that she and her hubby Javi were regular partners of James and Tonia. Javi couldn’t make it that night but normally he would have been there. And Casey! Oh my goodness. You could have knocked me over with a feather. You know how you joke about how her favorite color must be beige? Let me tell you, that girl is hiding some surprises under her frumpy exterior. At first I didn’t even recognize her. She had her hair all slicked back, heavy make up on, and the outfit she had on had come straight from the racks of that boutique! She had on high stiletto boots, long gloves, a mini skirt, corset and a collar, all of it a bright and shiny red vinyl. She made quite an impression! Ha ha ha!

It was SO WEIRD chatting with these people who I knew so well in such a strange and charged environment. But they were all very welcoming and kind, and every single one of them were excited about you possibly joining the cool gang in the future. Don’t worry. I didn’t make any promises on your behalf. I know how you hate it when I volunteer you for things. We can talk about it next month. Between you and me I’m not sure my jealous heart could bear it. I am such a hypocrite! And I’m not secure like you are. But we’ll talk in a couple of weeks. Maybe I’ll chill out about it by then. I never thought I’d ever get this far so who knows where I’ll be in a another two weeks.

The ‘event’ of the evening ended up being strip poker. I was told that because I was new I could ‘cash out’ at any point and either stay to watch the rest of the game or leave and there would be no judgment on me either way. They had their own kind of special variant of the game. Each round the person with the lowest hand had to take off a piece of clothing while the person with the winning hand could either put a piece back on or make one of the other players take off a piece as long as it wasn’t their last. Once someone was completely naked they lost and joined ‘the pot’. Alternatively they could ‘all in’ for one more hand. If they won that hand they could put three items back on and continue to play and if they lost they had to masturbate right then and be eliminated from the pot, but still had to stay to watch. The game ended when there was one person remaining with any clothes. The winner could then choose anyone who was in the pot and those two would have sex in the way the winner wanted while the rest watched.

Well, you know me. I was blushing SO HARD and wanted to just shrink and hide away in a hole and never come out. They all had a good laugh at my embarrassment and explained again that I only had to go as far as I was comfortable with. The fact that they were all so nice and that the group was mostly women who I knew and trusted really helped me find my courage. And so, believe it or not, your bashful wife entered her first game of strip poker. Around James and Tonia’s dining room table the cards were dealt and the five of us began.

You’ve heard about beginner’s luck? It’s a lie! Ha ha ha! Oh my God, David, your wife had the worst luck ever! Before I even knew what was happening I had lost the first three hands and I was wishing that I had worn a lot more clothes than I did. HA HA HA! They took it easy on me and allowed me to count my earrings as clothes but I was already planning my escape. Thankfully lady luck showed me some mercy and I actually won the next hand and put back on the sock I’d removed.

After that we settled into a regular rhythm of winning and losing all while continuing to chat and joke. It was the strangest combination of high tension and laid back conversation I’d ever felt. Very gradually the clothes came off. I was darned embarrassed for sure, but I didn’t feel nearly so freaked out once I saw the others losing theirs as well.

Two things quickly became evident as we played. The first was that Casey had the luck of her Irish heritage and the second was that Maria must have crossed paths with a black cat on her way there. Ha ha ha! Poor Maria hit a bad streak and couldn’t win a hand! Needless to say she was the first one out. The others immediately began to hoot and laugh and say saucy things while Maria gave us quite a show as she removed her panties then plopped back down on her seat as proud as could be. I was giggling like a crazy person and blushing so hard my face burned at the whole spectacle. It was so wild sitting next to her with her just sitting there completely naked. She was so confident and comfortable with her body! She’s a bit on the hefty side but I tell you that her good natured confidence made her even MORE sexy than those women in the adult movies. I never realized how much attitude could make a difference.

Maria going out ended up being bad news for yours truly. I’d been holding my own until then but, David, try as I might all of a sudden the cards just weren’t coming my way. Bit by bit by bit my clothes were coming off. I started with my socks, then my watch, then my necklace, and then things got serious. James won the round with two pair, I lost with a Jack high, and I had a decision to make. It was either blouse or jeans. Tonia suggested my wedding ring but I told her flat out that the ring stays on. In the end I chose my jeans as my legs could be sort of hidden by the table. GAH! Peeling out of my pants with all those eyes on me!? Just staring at me!? OH MY GOD! I felt even more naughty than with Bradley the other night.

As it turned out my big decision between jeans or blouse was made moot by James choosing me to strip another piece! HA HA HA! I told him that he was bullying the newcomer and that he should really put something back on himself as he was down to his briefs but he was adamant and the girls backed him up. Again Tonia reminded me that I could back out, no questions asked, but seeing Maria beside me in the buff…I don’t know. I didn’t think it fair. And so, off went the blouse. They always wait for the strip before dealing the next hand and so everybody sat there watching as I undid each button of my blouse. My heart was going crazy and I got that tingly feeling again. For a few seconds they just looked at my body then they started saying the nicest things about how I was really hot and about how lucky you were to be married to me. Maria even joked that Javi was going to be one happy man if I was joining this group permanently! Ha ha ha! They were so nice. Made me feel sexy.

James picking on me ended up coming back to bite him as the very next hand he lost, big time. I was so full of nervous energy that when he slipped out of his undies…I pointed and giggled! AHHH! The whole table roared with laughter. Casey darn near fell of her chair she was laughing so hard. I was SO embarrassed. I felt awful! I didn’t mean to do it. I swear I didn’t. I told them that it was just such a surprise at seeing another man naked and the way his penis popped out like it did. Thank goodness James and the rest took it all with good humor. Don’t you dare breath a word of this but I actually giggled because he was small! Not super small or anything, I would guess around 5 inches or so and skinnier than yours, but smaller than any I’d seen. I just hadn’t expected it. It was kind of adorable in its way.

James then shocked the table by going all in! He said he wasn’t about to pass up on the opportunity to welcome the new girl properly. I’m still not sure if I was flattered or aghast at the lewd way he said that comment. Tonia reminded him that I might bow out at any point but he said he was willing to take that chance. Long story short, Casey won and he lost.

And that’s when things really got surreal. By their rules we couldn’t deal until the last round was done and so the four of us ladies sat there and watched James masturbate. He pushed his chair back to give us the full view then started stroking himself right there in the dining room. It was kind of funny, kind of pitiful, and kind of hot all at the same time. Without the other women there I never could have sat through it but since they were I was able to sort of blend in with the crowd like I had with the strip show. His own wife teased him for letting his dick rule his head and said that he was getting what he deserved. Meanwhile Casey kept saying ‘faster, faster, keep going’ and never let him slow up for an instant as we still had a game to play. Maria texted her husband to let him in on the fact that James lost an all in and he quickly got back to her saying that he was glad that he wasn’t the only one who would have to resort to his hand tonight! Ha ha ha ha! That Javi always was funny.

I had never watched a guy pleasure himself before. It was so interesting and arousing though I can’t say precisely why. For awhile James tried to play it cool and crack some jokes and stuff but it was completely obvious to see how excited he was getting. He kept looking at Maria’s naked body and mine in just my bra and panties then around at the four faces watching him all the while his face was getting redder and his breathing quicker. Casey started to tease him and say things like ‘tick, tock Jimmy, we’re all waiting’ and stuff like that while the other two started saying all this super sexy stuff. Maria even began to moan as if she were the one pleasuring herself. His orgasm came pretty quick and we all let out a big cheer like it was a touchdown! He he he!

It was all quite funny in a way but oh my goodness, as I watched him lose control all I could think about was you! Why hadn’t we ever done this? I knew that you masturbated, why hadn’t I ever asked to watch? I wanted so bad to see my man lose control like that! I want to see that! And I want you to see me like that too! That would be so sexy! You and me were missing out on so much and I knew why. Because of me and my limitations. Well the new Sarah won’t be like that. You’ll see Papa Bear, you’ll see.

The others all gathered around him to give him kisses and tell him he did great. He chuckled and huffed and soaked up all the attention with a big smile on his face. It was all very sweet and wholesome in a kinky sort of way. As he cleaned himself up we carried on with the game. It was only then that it hit me that there were only women left in the game and our one man had taken himself out of the pot. When I brought this up the others just looked at me and chuckled. These people didn’t just swing, they swing both ways! They carried on as normal but I have to confess that I was flummoxed.

With James out my luck turned sour once more. My panties came off the next hand and my bra on the one after. A part of me wanted to bow out but with two people already naked I felt pressured not to chicken out. I can’t even describe what I felt like sitting there in another house without a stitch of clothes on my body as all these people stared at me. I tried to act confident. I tried to act like Maria. But sitting there, totally exposed and painfully conscious of it, I would unconsciously cross my legs or cover my breasts with my arm then force myself to relax again. My whole body was on fire. I just can’t describe it.

The game continued on with just Tonia and Casey but all I could focus on was my own nudity. Hyper aware of my state I caught every glance and every ogling look from the others and it drove me wild. They could see me. All of me. Every bit of me. I was so ashamed yet so turned on! Even writing this I am blushing, but I was so wet that I was starting to leave a little puddle on the seat of my chair! And then I became paranoid that they might see it, which made me even MORE horny! AHH! They were all looking at my naked, married body. A body that I had saved for you alone like a good girl all this time but was now putting myself on display like a very bad girl. They saw your wife David and I let them see me. It was so sinful and so hot! I was burning up! Had I gone all in and lost right then I would have orgasmed faster than ever!

I couldn’t take it anymore. David, I just couldn’t take it. I knew Casey was probably only a few hands from winning and I was curious about watching what happened after but I blurted out that I was going to go. Trying to be sneaky about it I used my panties to dry the seat as I got up then hurriedly got dressed, not even bothering with my underwear. They paused the game and all thanked me for coming out. They said that they hoped they’d see us soon and that they’d see me in the morning.

I drove straight home, ran straight for the room, and made straight for Mr. Purple. When I took them off I discovered that the crotch of my jeans were damp! I was so wet! I’d barely gotten the vibrations going and I was curled up on the bed in one heck of an orgasm.

Whew! What a night! And now I’m about to go face those women in half an hour. Ha ha ha! I can already hear the kids asking ‘Why is Sarah so red?’.

Another long one and now I’m running late. Dang it. Love you! Miss you! Thinking about you A LOT! Supper in the fridge.

Lucky in love but unlucky in cards,

Sarah

Nov. 17th