30 Days: Nov. 22nd (Patreon)

Dear David,

You are the best husband ever! Period. Oh my love, you made me feel like a queen last night. Flowers? Foot massage? My favorite take-out? And cuddles galore? Ohhh, David. It was wonderful. What did I ever do to deserve the perfect man? Whatever it was I’m glad I did. That’s you in a word David. Perfect. Perfect…but with room for improvement. He he he!

Hold on. Don’t make that grumpy bear face. Let me tell my latest story and you’ll understand what I mean.

I was one happy woman when you left the house last night. Not just happy, but horny too. Being treated like a queen will have that effect on a girl. I wanted to jump you so bad last night but I stayed strong. Granted, it was easy to stay strong when I knew that I’d be getting some nookie as soon as you left. LOL I wasn’t about to let all those good feelings in my pussy that you’d worked so hard for just go to waste now, was I? He he he! So as you headed off one way I was soon in my car driving the other.

Earlier that day Casey and I had been chatting about what happened with Richard and she suggested that if really wanted a ‘friends with benefits’ arrangement that I ought not to rely on the ‘weaker sex’. Ha ha ha! Yeah, she called men the weaker sex! Now that I’m really getting to know her I am learning that she is quite a character. She doesn’t seem to have much nice to say about males or even their ‘snotty’ kids for that matter. Don’t ask me why she chooses to work in a daycare!

Scared isn’t quite the right word for it but I was feeling uneasy as I drove to her condo. I’d never been with a woman before and I really didn’t know what to expect. I’d decided the week before that it was something I was going to do before Naughty November ended but once I was actually going to do it, with one of my coworkers no less, the nerves were rising. But I’d had nerves before and seen it through so I knew that I could do this too.

She buzzes me up to her suite and then puts me on the back foot right away by greeting me wearing only a smile and a leather bikini! The whole inside of her place was all blacks and reds with erotic art and photography all over the walls. I tell you, that girl is two different people. Her work self and her home self. I never would have guessed such a wild woman had been hiding beneath that bland facade all this time. Blushing as usual I enter, not knowing what to expect.

The evening starts out normally enough. She makes us some virgin cocktails then we lounge awhile in the living room and share some small talk. She was very excited by the fact that you and I were now cool as well as the opportunity for her to get me before James had a chance. I get the sense there’s a bit of a rivalry between those two. After awhile there was a bit of flirtation by her but it was more to make me comfortable than to woo me. It was both flattering and WEIRD to have this woman that I knew so well in a different context come onto me. Once she had me comfy and laughing she then casually asked, ‘Ready?’. Not wanting to slow things down or give myself the opportunity to chicken out I answered yes.

She takes me by the hand and leads me down the hall to her bedroom. If the art in the living room was erotic the stuff in her bedroom was downright pornographic! With not one male body in sight. And on the bed, oh my goodness! Ha ha ha! She had this harness, she called it a strap-on harness, with a whole line of dildos in a rainbow of colors laid out from small to humongous! Or I really ought to say medium to humongous as the smallest one she had was about your size, not one of them was down around James’ size.

As I blush and sputter and cover my face Casey doesn’t waste any time before she asked me to ‘choose my pleasure’. Giggling like a nut I stood there not sure what to say. She then assured me that we’d warm up to it and that she wasn’t about to just throw my down and ‘bang away’. Eventually she calms me down and starts asking basic questions like how big yours was and how big the biggest one I’d had was and how they each felt and stuff like that. The way she spoke it reminded me of a kindly teacher or something. But it did the trick. On this particular adventure I was grateful to have an experienced guide.

So I show her your size and the size of Mr. Sticky, she actually knew the exact model, and then tell her that I enjoy both in their own ways. She grinned and said something like, of course you do. Eventually she cajoles me into choosing one. I chose a nice pink one roughly size down from my own dildo and what does she do? She grabs the glossy black one two sizes larger and says it’ll be perfect. When I protest she tells me that married girls never admit to what they really want and that I should trust her. It was intimidating but she seemed the expert so who was I to argue?

She puts away all the other toys then hooks the chosen one up to the harness which she then sets on the dresser beside a little pump bottle of lubricant. And then she turns to me!

The next thing I knew I was in her arms being held and caressed in such lovely ways. She begins to kiss me on my cheeks and down my neck as she softly stroked my hair. Being touched like that by a woman was SO different than I was used to. There was no stubble or extra hair or anything like that. Her body, her hands, her lips, everything was softer and gentler. Like silk compared to wool. She smelled nice, felt nice, just was nice. And soon she was unfastening buttons. She peeled me out of my shirt and tenderly kissed my cleavage as her hands roamed all over my body. Again it was different than with a man. She didn’t go straight for the boobs, butt and coochie but took her time to give all of me attention. Shoulders, arms, belly, everything. It was so sensual. And the ways she would run her nails up my inner thighs? Ohhhhh. She had me swooning.

So caught up in the ride she had my bra and skirt off before I even really knew what was happening. She took off her top and she nibbled at my ears our breasts smooshed together. I’m a lot bigger in the bosom than she is and her sort of got engulfed in mine. Her nipples are a lot bigger than yours and puffed up stiffer. It was all such a new sensation! The next thing I know I am naked and on her bed. With a burning look of desire in her eyes she slowly, teasingly, kissed down my flesh until at last she finds my pussy hot and wet.

And THIS is where I talk about room for improvement. OH MY GOD! The way Casey ate me out was…I can’t even. She was so good! Not just with her tongue either. She used her lips, her teeth, her chin, her fingers, everything. She got into every fold and sucked every ridge and had this way of fingering me that had my toes curling. She knew just how and when and where to touch and for how hard and how long to do it. I’d never had such incredible foreplay before. She made me orgasm in the most natural and gradual and effortless way that I glided into it as easily as dipping into a warm bath. Magical!

Now she’s got an unfair advantage as she knows what it feels like to be a woman, but still. If you want to give me oral as good as her you’ve got some learning to do baby! You’re not going to let a girl do better than you, are you? Ha ha ha! I’m just teasing.

When she came up after my climax she quipped that I was ‘easy to please’ and that we were going to have some fun.

I lay there all flushed as I watched her don her harness. I actually laughed when she pulled it on and suddenly there she was with the big boner sticking out. She shot me a wink as she stroked on a bit of lube and said that I wouldn’t be laughing for long.

She was right!

With her phallus she teased my coochie as she played with my breast with her free hand. She had me moaning and squirming and begging her to fuck me. I couldn’t believe the words coming out of my mouth. This wasn’t you or Richard, this was my coworker! But like a shameless little hussy I begged her for her cock.

Oh David. When she finally put that big cock into me I darn near climaxed on the spot. A little bit thicker and a little bit longer than my toy hers actually ached as it stretched me out and went in deeper than I’d had before. But it ached in a good way! Yeah, I wasn’t laughing any more.

She fucked me from the top then had me ride her for awhile so she fondle my big breasts and then, at my request, took me doggy for good long while. It was different seeing a woman over me with her breasts and everything, but it was undeniably arousing. And just like with her oral she just had this sixth sense of when to go hard, when to go slow and deep, and when to back off again. And oh my goodness, the things she made me say! She would wait until she was going at me really hard and I was on the cusp of climax and start asking me things like if any man had ever fucked me so good and if my husband’s cock ever got so deep then said things like ‘David’s little pecker will never make a little slut like you feel this good’ and all sorts of wild things. I blush to say that I screamed all sorts of answers back. All the stuff she wanted to hear. Stuff I normally would never say. Stuff I didn’t even mean. Not in the way she meant them at least. But I said them to her. I couldn’t help myself. I was putty in her hands. And oh my God did I cum for her!

By the time she was done with me I was DONE, period. I apologized for not being able to return the pleasure but she said it was all cool and that she got what she wanted out of me. She said something like ‘good luck to James in following that’ and laughed. She’s a strange one that Casey. After a little while of holding each other as I recuperated I asked that she apologize for some of the things she made me say. And she did. She said that in the heat of passion that sometimes things got said and that I should take it so seriously. She’s right of course. It’s just sexy talk to make the moment spicier. Yet another thing I’ve got to loosen up on.

After that we had a really nice long conversation about sex. She really opened my eyes on some things. She suggested that we try a cock sleeve on you when I was in the mood for extra thickness. Ever heard of them? She also suggested we buy a strap-on to use on each other. I laughed at that one. A strap-on on guys!? But she swore a lot of men liked it. James for example. And then she said the strangest things. She said that if we like No Nut November that we ought to try ‘Locktober’ next year and that she would be happy to ‘cucksit’ you while I’m out having my fun. I didn’t have a clue what she was on about. I was so tuckered out by that point so I just sort of hummed and nodded along.

Oh my goodness. My coochie was so tender as I got dressed for home. I felt sore but so good as well. She chuckled as she saw me hobble along, looking quite proud of herself, and saw me to the door. It was a surreal moment when for a moment she turned back into the regular Casey that I’ve known all these years and said that she’d see me at work in the morning, then with a smirk added at the end ‘my little slut’. And now I’m about to go see her at the daycare. WEIRD!

Looking back at the experience I’m not sure how I felt about it. Her foreplay was some next level stuff. And the strap-on sex definitely made me orgasm good. Really good! And yet…honestly? I enjoyed it but I didn’t like it. Does that make sense? I would do it again but I’m not going to seek it out. To put it plainly, I like men. I like being the soft one. I like being the princess. And I like seeing a man feel me as I feel him. The big strap-on was great but it lacked that physical connection I crave. Casey was too in control the whole time. She couldn’t feel me like I felt her. And I never got to see that wonderful build up and moment of surrender I get with men. Besides, Casey for all her efforts just didn’t have that ‘oomph’ of a big strong man.

Anyway, it was a learning experience. I had a great time with Casey and I’m glad I did it. I’m still feeling it this morning! Ha ha ha! That girl is wild.

I still can’t believe you have to work tomorrow. It’s Thanksgiving for goodness sake! Can’t they not have gasoline delivered for ONE DAY? Don’t they know that they have to share you with your wife sometimes? I know we’ve already talked about it, but it still sucks and I wanted to say so. Speaking of Thanksgiving, I think I’m going to take that day off from our challenge. You’ll get a letter tomorrow but not the next day. It’s a day for family. You had that one little lapse so I think it’s okay if I have one too. Besides, I could use the break! A girl can only take so much! Whew!

Sore but satisfied,

Sarah

***

Still sore this morning? I’d never heard her say that about me. Or Mr. Sticky. Damn that cock must have been big.

Last night I’d been cucked by a drab, boring, plain-looking woman named Casey. I’d been cucked by a woman! I didn’t know if that made it better or worse. Not just any woman either, but a woman that my wife saw every Monday through Friday. A woman I would be talking to every time I popped into Sarah’s work and every time she got invited over for a barbecue or what have you. Bradley only rolled through town every now and then but Casey was one of Sarah’s close contacts. I could already see that knowing gleam in her eyes the next time that she and I saw each other. The gleam that would say ‘I fucked your wife and I did it better than you’.

“Fuuuck.” I push down the erection straining my pants and feel a copious smear of precum already wetting my underwear.

Casey hadn’t just cucked me. She had overtly and purposely cucked me. Husband never got so deep? David’s little pecker? Better than any man? Cucksit!? My wife’s coworker had set out to fuck Sarah better than I could and she’d succeeded. And Sarah, Casey, and I knew damn well that she had. The tendrils of this challenge were spreading wider while also creeping closer to home.

I should be insulted. Furious! Scared for my pride and worried for our reputation. This stuff was really happening. With real people. Out there in the world. It wasn’t contained to these little square envelopes like it seemed like through my current lens. Again I knew I ought to stop this. And yet… And yet… And yet…

“Hahhh.” I take the letter and stand to make my way upstairs. I couldn’t think clearly when I was this horny. A nice long fap session would cure that. Well…with the hair-trigger way I was feeling right now, nice and short would have to be good enough.

Nov. 23rd