Ep. 02 - Wees 3-7 of the Game

Below is an abridged series of text messages following the discussions from after week 2.

M: "Glad to share a great night with this very special lady"

A: "Thank you for making me feel sexy for a few hours before I go back to normal me"

M: "That's what this is all about, making you feel confident in who you are. If we can do that it's worth it. Just happy we can talk and share and have fun together. I'm smiling more for sure - it was nice to be having fun sexy kinky conversations with you more and more"

A: "I'm glad we opted to work on our connection. It was what we needed and I think it'll pay off for years to come"

M: "Absolutely. I've always been very compartmentalized so this hasn't been easy for me to say the least. Much easier to close myself off than to take some risks. But I felt like we needed a change as we were moving in directions that weren't great for us and you being more comfortable and open than I was expecting helped so much"

"I've had fun slowly opening up windows into me. This game has helped make it more measured release and a better framework for sharing when we are both ready for it. Like there are some risks in there for sure but they could come up in 1 week, 1 month, or 1 year - it's all up to chance. And that keeps me on edge a bit, but in a good way. Like if I was directing the order of events it would be in a specific sequence but I know in reality it will actually be anything but, so I submitted my cards and now I'm just along for the ride"

"Thank you for making this easy and I love you. I never thought we would get to this place so you are already blowing away my preconceived notions. Kind of the 'I've accepted that we'll have fun but only in a purely vanilla way long ago.' I know you've had father to come than me and I respect you so much. Love you and I hope you have an amazing day."

A: "Thanks for being vulnerable. I've had farther to come just because I've never felt conventionally 'hot'. Part of that is growing up as a woman in the early 2000s when curvy Jessica Simpson was considered a "fatass" and everyone wanted to look like they were Eastern European teenagers with a heroin addiction. I think making being modest and understated kinda my "brand" was my defense against feeling less-than in that environment - but I don't really need those defenses anymore"

M: "You are a beautiful lady. Embrace it."

A: "I love you. Thank you for making me feel like this"

M: "But seriously right now it feels more like the summer when we met. Conversations are more fun, playful, and with us putting in more effort than the last few years and I think we are both enjoying it. Kind of like start of dating again."

"That initial period when txts and conversations could be about getting to know the other person, when and what to share, and playful back and forth more than 100% real life boring stuff."

"For instance I'm actually excitedly looking to see what you say next and riding edge of my seat again. That's not a feeling I've had in a while."

A: "I was thinking the same thing. I loved the exhilaration of trying new things and the confidence that comes from sharing a secret with you."

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Week 3 of the game A rolled a 5. This was the first time that M had a card come up.

If we are keeping score it's 2 cards for A, 1 card for M thus far.

The card had a drawing of anal beads that specified they were to be used on A and that M would eat her out at the same time.

A took it in stride and agreed to the suggestion. A was surprised that M had beads already and even more so that they had been his for a while. Given all the heavy Thanksgiving meals we put it off for a bit until we got back on our normal routine. Waiting for the right time vs forcing was a key discussion point for M&A and a healthy communication to have during any anal play. M showed A the beads so she could better understand the device (pretty small) and do her homework.

A few days later, A signaled she was in the right place. A expressed concern about losing focus with oral sex too but M thought it would be a good distraction vs focusing only on her ass, particularly given it was her first time letting M play down there (previous butt plug usage was put in by A and taken out by A).

M sat down on the bed and A climbed on top to make out. Shortly thereafter, M laid fully down and helped slide A further up to where her hands were on the headboard and her pussy was over M's face. M had been pushing the boundaries on cunnilingus for a while but this was the first "facesitting". A seemed a touch surprised but once M signaled he comfortable there A began to get into it.

After a few minutes of pre-game warmups, M slid out and put A on her back. M started licking her folds again and then put a generous amount of lube on his fingers and warmed up her ass. This was quickly followed by the first bead. A felt that first bead and her tightness began to fade, quickly replacing with eagerness as she began fingering herself and asking for more oral.

M slowly worked in bead by bead, generally getting prepped for the next one and waiting for A to request it. The toy has ~9 beads of graduating sizes M&A played for a while with the first 3 moving in and out before M suggested that A switch to the ride on attachment to the Jackhammer. At this point, A was fighting off an orgasm and trying to savor it as much as possible before it hit. M focused on using beads 4 and 5 at this point and A went past the point of no return and came hard.

After A came down from her high, M slowly pulled out all 5 beads which almost re-triggered A. At this time M began fucking A and came hard in short order, particularly after A got on top and began thrusting her hips hard. After finishing, M suggested A finish off with one more Jackhammer before getting out of the cowgirl position, and lifting herself off of his cock.

A remarked that she had fun and would definitely try beads again so M&A decided to keep that in the deck.

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A rolled a 9 which was 2nd week in a row that it would be M's suggestion. For those keeping score it was now 2 for A and 2 for M.

The card read:

"She's a powerful warrior lady"

Let's try the amazon position. There are several variants so come prepared what you think is best.

M had seen this position many times in online videos and really liked the concept. Given A's love for getting on top, this felt like a natural extension that put A in the drivers seat with even more control. M had suggested this once before while having sex but given that it was foreign for A and she is more of a visual learner it was quickly abandoned in favor of the known positions.

To hopefully have a more successful 2nd attempt, M sent A a few videos in advance and got a discussion going. M sent a few from a popular porn site but this was an epic fail as A was too overwhelmed between a longer length video and all the ads and banners. Rather than trying to change her viewing habits, M suggested A try and do her own research and she chose to look at the r/amazonposition subreddit. This was more typical of A's research and she quickly discovered that the short clips and lack of ads kept her focused.

After watching several including from u/AmazonCouple and u/TabbyNoName, A told M that it looked fun and that she understood the general concept. A was quick to point out that many of the versions required a level of flexibility that we might not have right now and M agreed, signaling that it was more important to him to try than to succeed. With that the stress level decreased and A was more willing to experiment.

The first attempt A tried for a more traditional position with her feet flat on the bed and knees bent - this felt really good but both M&A were exhausted after only a few pumps. That night we quickly pivoted back to the old standards.

While M agreed that the card had been fulfilled, he suggested that A try again during the week with a standing position and sent a video specially of that. A agreed to try and a few days later was attempt #2. A put on some Quim lube and M put on a vibrating cock ring, both which would have given A maximum stimulation. M scooted to the end of the bed and angling up while A mounted while standing next to the bed. A got a few pumps in putting one leg on the bed for a hybrid Amazon/cowgirl. That seemed to work best for us and we enjoyed that position for a while before defaulting to regular cowgirl to finish. Afterwards, M suggested a pillow might have helped more to push his pelvis up even more which sparked a good discussion about sex wedge pillows.

Morale of the story, not all suggestions will be winners right out of the gate. Some might come with time and some might not be repeated, but M&A both enjoyed getting out of the standard comfort zone.

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For week 5, A rolled a 3. Another suggestion from M.

Let's go to Tokyo Valentino together and shop for something of your choice. Commentary encouraged while browsing.

(For those not familiar with Atlanta, Tokyo Valentino is the fancier local chain of sex toy stores, though lots of people go there not for shopping...)

A got pretty excited about the prospect. While A had the beloved Jackhammer and a smaller rabbit before M, the toys have really grown in the last few years, especially after the introduction of Sexy Christmas in 2022.

We decided to browse through all the rooms first. The first room was very vibrator heavy and A took interest in the bigger rabbit vibes and was curious about the thrusting rabbits but decided she needed more research.

The next room was a lot of dildos. A couldn't believe the size of many of them and audibly doubted that people actually could take several. M used that as an opportunity to share a bit more about a previous relationship where an ex had multiple very large dildos for personal use. "Big Freddy" which was probably a 10" long white dildo, and then the infamous Bam Dildo which was approximately 13" long and coke can girth. A was surprised and impressed yet also made clear that wasn't her idea of a good time. But the vulnerable sharing helped break some tension.

The 3rd room was more bondage focused and one where we lingered a few times with various commentary. A seemed quite interested in a Liberator wedge, especially after recent challenges getting the right angle in our play. The last room was a lot of costumes and lingerie.

Ultimately, M&A decided to go with the Liberator Ramp/Wedge combo but opted for the Black Label version with a blindfold and beginner handcuffs. A had previously laid out hints that she would enjoy some light bondage play so this seemed like the best opportunity to knock out two birds with one stone.

Later that night, M took charge and directed A to get naked and lay on the ramp. M said that he was going to periodically squeeze her hand and if A squeezed back twice he would proceed. Consent is important and making sure that both partners are comfortable.

A was very receptive and after making out for a while, M attached the first wrist cuff, clipped it to the ramp and checked in with M. Two squeezes and he proceeded to make out and attach the next cuff. Same check in and response. Next was the blindfold and A gave her consent.

At this point, A's upper body was relatively immobilized with her hands clipped up by her head and her eyes blindfolded. M got off the bed and took some time to get prepped and ready. M got the Jackhammer, the dildo attachment for the Jackhammer, and plenty of lube. M ran the jackhammer slowly all around A's body which sent shivers and then focused on her nipples. After a bit, M spread A's legs and then started to stimulate her clit and put a finger on A's asshole. As A's breathing got heavy, M pulled away the Jackhammer and attached the dildo head while A cooled down. Next was dildo jackhammer and a pinky in A's ass (first time insertion). A got really close from this and then begged for M's cock and it wasn't long at this point.

M&A thoroughly enjoyed the evening and loved that this card really helped open up a lot of options for the future by introducing bondage.

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On Week 6, A rolled a 15. This was the 4th M suggestion in a row.

*Whether I should call you Miss, Goddess, Mistress, Lady, Queen, Princess, Empress, Mommy, Daddy, Your Grace, Your Majesty, Teacher, My Love, or My Darling...whatever you say goes. *

As with some of the other bigger/spicier challenges, A took a bit to process it. M reassured her, indicating that it was a role play.

A announced she was considering different things every day or two but didn't indicate much else. Finally during date night, A said she likes it when M calls her Baby. M pushed back a bit that it would be nicer to have a bigger difference from normal nights but A insisted. M was a bit dejected but ultimately agreed to all of A's wishes without pushback, always saying "Yes Baby". A didn't seem sure how to approach that, though her willingness to accept the reins grew over the course of the night.

M have A several options for A to choose to get her making decisions, including offering up a few different plugs for her to select for him. In bed, A grabbed the Liberator Wedge and had M lay back against it. This gave a considerably different angle when she jumped on top for cowgirl, partway between laying down and sitting up but very comfortable for a long ride. A was the aggressor and initiated lots of hard thrusts and kept M on edge for a long time before she came. After rolling off and cooling down, A suggested that M jerk off while watching her use the Jackhammer on herself. As M got close, A indicated that she wanted him to cum on her tits. Quickly thereafter A came and then M came in rapid succession blasting A.

In the shower after, M leaned down and kissed A's cum covered chest and then gave her a passionate kiss, though A indicated that wasn't her jam.

As the night ended, A mentioned she isn't sure Baby is the fit she really wants and is going to think about a new title.

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Week 7, A rolled a 2.

* You pick the outfit, ill wear whatever you want*

This was the first repeat card, but it was a great one. M had an idea almost immediately, but didn't reveal his hand.

Kinky play slowed down during the holidays and travel so it had to wait a week. On the way home from the holidays, M leaned over and said that his request was for A to wear her dirndl. M had had a thing for women wearing that corseted German dress, but that really accelerated after attending Oktoberfest in Munich several years back. A was very excited.

That night, M asked A if she wanted him to hang out downstairs or watch her throughout her outfit prep. She told him to watch. After a sensual shower, M got on the bed, inserted the Aneros prostate butt plug and slowly rubbed himself as A proceeded to get dressed.

A hoped onto the bed, straddling M and starting to make out. After a few minutes, M slid down and encouraged A to slide up and onto his face. This was the most face sitting we had done to date and M really enjoyed being under the dirndl's skirt. A got close, but then demanded M's cock and M&A flipped over into missionary with the wedge.

M's long, slow, hard strokes brought A to the edge before she wanted to finish on top, this time in Reverse Cowgirl. A rode hard while rubbing her clit, and it didn't take long before M came very intensely, bringing A over the edge. A had a leg shaking, screaming orgasm unlike ever before and remarked how she was going to be feeling that tomorrow and will remember that feeling for a while.