Chasing Me Chasing You

An uncollared submissive struggling through depression, motherhood, and the constant craving of her next orgasm.

California Dreamin’

Jack and Jill fucking on their bed.
Jack and Jill giving me a lovely show.

If you missed the begining of the day – Meeting Jack

First Volley – ‘May I kiss you?’

We weren’t naked for long before we couldn’t keep our hands off one another. As nervous as I had been waiting for him at the airport, I wasn’t embarrassed to be naked with him staring at me. We admired each other between orgasms and our mutual astonishment at how well we fit together. As we lay in a post-coital stupor we began realizing how much we had in common. Nothing is sexier to me than having similar ideologies to talk about.

The only thing that kept throwing me as we cuddled for awhile and then took a lovely shower together, was his concern. He would ask if he could kiss me or if I was doing okay. Don’t get me wrong, it was beyond sweet. It practically made me gooey whenever he would ask me. I think it just threw me as Sir doesn’t usually get around to checking in unless I safe-word. If a whip isn’t involved, he usually doesn’t mind if I’m whimpering with tears streaming down my face. Jack must of thought I was deaf with the number of times I responded with, ‘What?’ whenever he would ask. At least Jill said that he does the same thing to her, so it wasn’t a horrific facial expression I was making or something.

Unsuccessful Oral – ‘I probably should have mentioned…’

So, sexually, I pride myself on two things. One is my boobs. I have no control over their size or shape, really, but I think they look pretty good most of the time and quite a few others agree. Two is my skills at giving oral sex. I had a not-so-pleasant first experience with oral and basically refused to do it until I met Sir. He was patient, but really wanted me to give it a try again under his tutelage. I’m sure he wouldn’t say that I was awful to begin with, but I think he would say that I’ve come along way since we met. And, given the few partners I have been able to practice on since, no one has complained.

Needless to say, I was eager to give my skills a thorough test on Jack. And I ate humble pie, my friends. I pretty big piece of it. The first day I was there I went down on him. I used all my best technique. Not quite the same things I generally do for Sir, but everyone is different. Even though I did coax the occasional moan from him, I just wasn’t getting him there. After about fifteen minutes my legs were numb and my mouth had stopped producing saliva in protest. I had to stop. And I nearly cried. I couldn’t believe that I wasn’t able to get him off. He told me that it usually takes him longer than other guys; that he should have told me that. But at that point I thought he was just placating me.

I told Sir about it that night when we talked. He could tell I was disappointed, but told me to take what Jack said at face value. He was proud of me for trying so hard. And he knew I would try again and do my best. It felt a little like I was talking to my old gymnastics coach, but surprisingly, it helped a lot.

Breather – ‘Don’t put your dick in crazy.’

After several rounds of lovely orgasms (after oral didn’t work he was able to use my pussy for its intended purpose) we decided to take a breather. We took a ‘real’ shower and begrudgingly put on clothes. I checked in with Sir as we curled up on the couch. The chance to chat about politics and family was nice as a break. Sharing child rearing tips and my position on teaching my boys sex ed (see above quote) was very calming. We were both trying hard not to get too turned on again before Jill got home so we could save our energy for after dinner. Mostly, it worked, though I was pretty gooey by bedtime.

I’ll admit it felt a bit weird as I listened to stories (all of them entertaining) of Jack’s relationships with other women. His wife (obviously), other couples, random hook-ups. I wasn’t necessarily comparing myself to them, but I was worried about how he would compare me to them. Only in the last few years have I really started to enjoy sex and embrace my inner slut. And my other non-monogamy experience didn’t go so well. So I didn’t want to become a negative story for him to tell future lovers (who does?). And, as much as I have put nude photos of myself on the blog and sent him photos and video by DM, I didn’t want him to be too let down by the reality that is me.

The fact that he kept calling me hot and sexy almost threw me off guard. Not that Sir doesn’t say it, but I guess I don’t really believe him when he says it either. I don’t know if it’s body image (probably), or they are just saying it to get me into bed. Though I guess for both of those people I was pretty much a sure thing, so I guess back to body image.

Jill’s Arrival – ‘Get that poor woman a drink.’

Jill had run to the grocery on her way home to get supplies for dinner. When she did get home we could both tell pretty quickly that she had had a rough day. I’ll admit I was a little out of my element. I wasn’t sure how to help while also sort of feeling like a third wheel. Even tired she still let us relax while she made a fabulous dinner. We ate while joking and sharing still more stories.

After dinner they each had a drink. I think it helped Jill feel more comfortable considering that Jack and I had already spent the entire day together. When we couldn’t take the tension anymore they pulled me down the hall to the bedroom. They undressed me and let me enjoy Jill’s soft skin. With her being so upset after a long day, I let them focus on each other for awhile. I was so intrigued by their connection that I took several pictures of them.

I just wanted to watch them for awhile, but that would hardly count as a threesome, would it? Instead I enjoyed massaging and kissing Jill’s body while Jack fucked her. It was nice to be ‘eased’ into my first threesome experience. Just watching them was amazing.

Sleeping Arrangements – ‘On the floor is fine,….please.’

When we got around to go to bed my nervousness returned. I had written a post about my unease and how to bring up the topic of where I would be sleeping. We had talked in DM on twitter quickly about it and then nothing else was said. So after a quick play session with all three of us on Tuesday evening, we all brushed our teeth and wandered around to get ready for bed. Jack decided we were all sleeping in the bed, sure that we would all fit fine. And, realistically, we did.

The submissive part of me wanted to ask/be told to sleep on the floor. But him deciding that we were all going to fit on the bed was decision made. After we were all settled under the covers he rolled over and cuddled with me for awhile. It was so nice. It’s not Sir’s fault, but he can’t cuddle with me and sleep. He overheats in an instant and laying on his side too long will mess with his back. So admittedly I wasn’t prepared for when he held me and then started to snore lightly. It was so cute (in a very manly way). He said later that he sort of went back and forth cuddling with Jill and I. It wasn’t a ton of room, but there were plenty of blankets and I think everyone  managed to sleep okay. Admittedly, my first night on the couch in L.A. I slept like a rock, but waking up alone dampened that pleasure.

Wicked Wednesday for post Stockpiled Cravings

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4 Responses to “California Dreamin’”

  • Jack (and Jill)

    I am big on checking in with my partner(s), especially when one has traveled unaccompanied across the United States for the purposes of letting me fuck her. Over time as my partner and I figure out a rhythm and pick up on nonverbal cues, this sort of thing lessens somewhat. It’s all part of that whole “not wanting to be someone’s bad experience” thing I mentioned. I’m glad it wasn’t a turn-off.

    Your advice about not putting one’s dick in crazy is spot-on, and something I wish I’d been advised as a much younger man. While I don’t judge the women I dated/fucked for their idiosyncracies – I’m far from perfect myself – even as a teenager I was annoyed by drama, and it would have been nice to know how to avoid it. Sad how ill-equipped I was for my relationships back then.

    If you really wanted to sleep on the floor I would have let you. Jill would have likely misunderstood, thinking I had forced you to sleep on the floor, and would have been mortified. Still, I enjoyed naked spooning time, and kissing your shoulder and neck the first thing upon waking.

  • Miss Scarlet

    What a fun and exciting account.

  • Marie Rebelle

    It sounds like you had a brilliant time together. Hope to read a bit more of your time together 🙂

    Rebel xox

  • Molly

    it is sounds absolutely magical… and ‘don’t put your dick in crazy’ is one of Michael’s mantras so that made me chuckle

    Mollyxxx

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