[cshorts] My (our) journey

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Re: [cshorts] My (our) journey

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VERY interesting conversation during post-play cuddle time this morning.

SL asked me to read her an erotic story as we were getting things started (not uncommon for us). It was about a male-female couple, the female of whom found women attractive but had never acted on it. Her partner was more sexually open and confident and supported her as she agreed she wanted to go to a strip club, then get a lap dance, then get more.

I asked SL if she had enjoyed it — there were parallels to our situation (she’s expressed interest in women before but never acted in it). She said she did and found particularly interesting the woman’s thoughts recognizing that she hadn’t tried before because she thought she would get too jealous of her male partner playing with the woman too (they were only talking about threesomes). SL said that’s a problem for her — that she has desire but thinks seeing me kiss and touch someone else would ruin it.

I told her that for me, it was fine: I am confident in her love and have found from chastity, even more than I realized it before, that I love seeing her experience pleasure and it would be a major turn on for me to see her with someone else. She said that didn’t solve her jealousy problem.

I then offered that if it were easier to bring a man in that would be fine (I’m pansexual but not romantically attracted to men so perhaps less threatening). She said not so much. Then I said that if she wanted to be with a women or a man, it would be fine with me if I didn’t touch them — that it could just be both of us for her (or me absent). She asked if I was being snarky or serious and I assured her I was 100% sincere. I pointed out how much I enjoy her pleasure, which she knows and I said, “sure, I might be frustrated, but what else is new since you’ve had me locked up?”

I see this, it it ever were to happen, as more of a threesome but focused on her — maybe formally cuckolding but I can’t see her getting into the version that involves humiliation — can barely see it as possible that she might someday engage in a “vanilla” relationship with someone else.

I was quite startled by this conversation— yet another major surprise in this weekend of surprises. We’ve occasionally chatted about her attraction to others before but she’s never wanted to have any serious conversation about possibly making it real. I still doubt it will ever happen, but this was the first time I started to think it *might* happen. Wow. What has gotten into her this weekend???
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Re: [cshorts] My (our) journey

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Wow. Just...wow. [Warning: wall of text. And, not uncommon for me, quite graphic -- I write this for me and for SL, to remember and relive. Feel free to not read.]

We had talked about spending all day in bed. I'm still here after 2pm...SL is taking a bit of a break to shower.

I got up early as I do on designated play days. Headed right out to the new NY-style bagel shop nearby ... it's been such a hit since opening last month that there is always a long line, and they've been running out of bagels around noon. I hoped if I got there close to opening on New Year's Day, maybe the crowd would be less -- and it was. So for the first time stayed to find out if they're as good as everyone is saying (l'm from NYC and there's a truism in California: "You can't get a good bagel out here"). These turn out to be excellent!

Then home to shower, anally douche, and shave. Anally douche because she promised about three or four months ago that she would try pegging me sometime, and I keep hoping today is the day and prepare just in case. Today, being New Year's, with a plan to spend all day in bed, I was especially hopeful, thinking I might even ask he directly -- which I've not been doing because I don't want to push her. She's only pegged me once before in 25 years. And then, inserted a butt plug to loosen up and prepare me -- and because it feels good, even if there was no additional action.

Then I finished preparing breakfast. Delivered to SL on trays in bed.

After eating I vaped (cannabis) before settling in for a foot rub. (Comment after all of this: "You should get high before every foot rub. It lasts twice as long!" Turns out I was going for two hours.) After, I slipped into the bathroom for a pee, and to remove the butt plug -- which SL had seen in me earlier.

Then SL pulled out the key and removed the cage! First time off since 3 November. Then, cuddling, kissing and hugging....until SL started torturing my nipples. Oh jeez ... for a mostly vanilla girl she can be quite deliciously vicious with my nipples. She gets me to the point where I start to wonder if I'm enjoying the pain or it might be too much, then keeps me on the edge for a while during which I learn that it's not too much ... I'm such a pain slut. This time she took advantage of my free cock to also tease it with her other hand, bringing me close to the edge down there, too. With some breaks to scratch her nails down the very sensitive side of my torso. Rinse and repeat. I think i as crying out more loudly than I have in a while. When I'm wound up like this, especially so orgasm deprived, I never feel like she goes at me long enough -- of course, that's not fair because as long as I don't have an orgasm I probably *never* want her to stop! But this morning, in any case, she kept at it for a delicious, fabulous period. Thank you my love.

But that was just the warmup. She got up and came around to my side of the bed... and got out the harness and Vixskin Buck. Had me help her strap up, then took my head and pushed me onto her cock as she stood by the bed. I enthusiastically gave her a blow job, almost able to believe it was the real thing - the vixskins are quite lifelike, and i had prepared (for using on her!) by leaving it in a tall cup filled with hot water, so it was roughly human body temperature. After a nice long BJ, she had me put a condom on -- to keep "second cock" (which she loved having in her vagina) clean. I also found the placement of the lower hole in the Spare Parts harness very handy -- I slipped two fingers in, found her completely drenched, and stroked her to her first small orgasm of the morning.

She pushed me back and told me to get on my hands and knees. She lubed up her cock and my asshole thoroughly with the boy butter I had standing by, waiting for this day. And then, she slowly but firmly entered me. No problems with entry -- felt great from the first movement. She could tell from the sounds I was making and started thrusting without a pause. Oh lordy...bliss. She fucked me hard, then let me fuck myself back onto her, then more thrusting, on and on. Much of the time the angle was right to massage my prostate and every time it got pressed there was an extra jolt of pressure. She regularly buried herself to the hilt -- it was so hot feeling her hips pressing up against mine. She slapped my ass a few times -- not hard or often, just enough for me to know if love it if she really smacks me some other time (no surprise there -- I always love it when she spanks or crops me, neither of which happens nearly often enough for my taste :)

After a few minutes, I guess as my moans and cries were rising in pitch and excitement, she said "don't you dare cum". I told her it wasn't a problem, at least yet: this felt amazing and was stimulating me deeply, but I didn't feel any sense of an orgasm coming. Very exciting... but in a different way.

All good things must come to an end. She slid out and I collapsed face forward on the bed ... spent, but not "spent".

Some more cuddling time, then as I slid my hand over her thigh, she spread her legs and invited me to caress her. I started with slow, gentle stroking, bringing her to two orgasms, enough to make her clench and pant, but not big enough to take the edge off her excitement.

Then she told me yes, indeed, she wanted my uncaged cock inside her. First she had me place the Liberator wedge I'll ow beneath her hips to put her in what we've discovered is her optimum position for my cock to hit her g-spot. Lube, then entry. Oh my! It's been two months since I've been allowed into her garden: being welcomed back in was heavenly. So warm and wet, so enveloping.

A quite vigorous fucking ensued. She had her wand going on her clit throughout, and started coming almost right away. It has been a while, but I hadn't forgotten my way around her inner geography: I played with the ring of muscle at her entry that she loves: rapid shallow thrusts just barely inside. I rubbed the top of my cock against her g-spit, a bit further in, which really drove her wild. And, something we've been doing more just in the past 6 months or so, I spent some time pounding all the way in, fairly hard. We've avoided that for years because of risk of banning her cervix (which hurts her like hell) but we recently re-discovered that she really likes me deep, some of the time, if I *don't* hit her cervix, and I guess we've been lucky. (Mid-depth, rubbing and pressing on her g-spit, still seems to be her favorite).

After a few medium build-up Os (I lost count!), she had one of her huge, explosive, yelling and eyes popping out of her head Os. And major squirting. Yum ... I love making her feel so good.

As she was heading up to it she told me "now" which was a clear order for me to cum with her. But, much to my surprise, given I haven't had a regular orgasm since 3 Nov (and no ruins since she told me to stop touching myself thru the cage several weeks ago) I wasn't on a hair trigger, and though I tried to join her, I wasn't able. Fully hard, very much enjoying myself, but the point of no return was not present.

I stayed inside her but stopped moving and collapsed onto her chest, where we lay panting and kissing. After a few minutes I thought I heard her say "do now what I told you to" -- that is, cum, so I rose up to my knees again, with her feet on my shoulders and hips raised by the Liberator, and started fucking again, very pleased to enjoy my uncaged cock lost in her warmth again. My excitement rose, but again, I didn't feel things heading to the boiling point. Meanwhile, with no external clitoral stimulation at all, just cock on g-spot, she took me by surprise as she quickly rose to another massive O, purely vaginal. She ejaculated much more this time, too, soaking both the Liberator and the bed sheet. Even more than 20 years since she learned to be mutil-orgasmic, I am in awe of how quickly, powerfully and multiply she cums.

But then she really was ready to collapse, and I didn't feel close, so I stopped thrusting and gently pulled out, collapsing next to her and taking her in my arms. We were both surprised that I didn't come -- quickly even. I thought it might be, in part, the long, multi-phase nature of this play session: SL got me worked up to a fevered, near-orgasmic pitch early on with the nipple and cock teasing, then things quieted down for a while while we transitioned to setting her up for pegging, then the pegging which was very exciting but didn't directly engage my cock, then a slow transition to PIV. I've trained myself through the years to have great endurance, nearly perfect control in delaying my orgasms to attend to my love's pleasure, so despite the long two months of denial, the old training may have kicked in and I was by this point of the proceeding operating (unconsciously) in endurance mode. (It has not been I frequent in the past that during a long session I fail to cum during PIV.)

The other thing: SL grabbed the boy butter to use as PIV lube after the pegging. I pointed out to her it was de-sensitizing: did she want that in her vagina. She said "let's give it a try and see what happens." Well, as described above, it appeared to have no effect on *her* sensitivity or responsiveness (jeepers!). But while I was feeling great sensations of pleasure, it was a bit muted (as it is in "endurance mode") and the benzocaine in the lube might well have been enough to prevent my O.

So, long, fabulous session. First pegging in some 20 years, and what a pegging it was! First cage release and PIV in 59 days. And still, despite orders, no orgasm. So I continue to ride the horny wave, and will continue in full attentive service to my love, and wonder when I might get to O again...
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Re: [cshorts] My (our) journey

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Ok then.

SL woke up feeling really crummy from her cold, asked if we could put off play session until late afternoon (she generally feels better as the day goes on). Sure. But then she proceeded to start teasing me in the cage, got me all swollen and straining against the bars...and stopped.

End of the day she said she wanted attention. Started by taking my cage off. I read her a story; she spent part of the time teasing me and torturing my nipples, part of it jilling off with her wand (and the fingers of my hand not holding the reading device working it inside her). Then she climbed on and rode me, with her wand, to another O (for her). Rolled off, onto her back, and told me to get between her legs and do my thing. (Missionary-ish is her favorite set of positions: we get the best contact between my cock and her g-spot in those variants.)

As I started thrusting, she looked me in the eye and said "don't hold back." So I didn't. Paced myself enough (and worked her g-spot enough) for her to have a big one first, but as she was peaking, mine began...and I didn't hold back. Oh my. First in 64 days. A bit overwhelming ... I lay in her arms for some time coming down to earth again.

No obvious post-O drop, a least emotionally. We'll see if my attentiveness or horniness slack in the coming days, but I feel very content and very loving this evening.

After dinner, she looked down at me (we're still doing CFnm) and said "time for you to go back in."
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Re: [cshorts] My (our) journey

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SL came back from a week long trip at midday. I made her lunch, then we vaped and I gave her a long foot rub. After, I asked: "What would you like now, a nap?" (She takes one most afternoons.) She shook her head: "I want your hard cock inside me."

She finished getting naked. We snuggled and kissed, then things heated up. She tortured my nipples, I jilled her off (fingers). Went down on her for the next three Os. More cuddling and fingering. Then she unlocked and removed my cage, and said "Now!". I asked if I should put on a condom (with desensitizing cream on the inside) to help me be sure to last long enough. She replied, "If it helps. You need to last until I'm done. You're not cumming."

I suited up while she grabbed her wand. I moved between her legs and we devoted both toys (cock and wand) to her pleasure. Two tremendous orgasms for her, then a short break before I re-entered and she had one more loud, thrashing O.

I lay alongside her to cuddle again, stripping off the condom as I moved next to her. She teased me a bit more. I said, "I haven't cum yet." 'Damn straight, and you're not going to. It's only been two weeks since you had one." A bit more teasing, an order that I wasn't to touch myself, and then she rolled over for her nap.
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Re: [cshorts] My (our) journey

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We'll be with our son Sunday morning, so won't have that regular play session. Today's sort of a work day for me, but away from office on a business trip and no scheduled meetings so ... flexible. SL (came on the trip with me) decided she wanted to play. Had me read (really hot) story to her. Midway through she started torturing my nipples and stroking my caged dick. She went further on the biting than she ever has ... I actually started crying, at the same time as I came as close to an orgasm as I ever have from nipple torture. This went on in variations for some time, all the while pushing me away whenever I tried to touch her. Finally she said this morning was just about me....which just made the teasing worse. Normally I at least get the satisfaction of making her cum. "No! You have to learn, I'm in charge now!" Now, as she showers, I'm lying here frustrated, my balls covered in leaked pre-cum, no hope of my release (it's been a month since the last, and I'm pretty sure she didn't even bring the key on this trip), and at least this morning not even her release. I'm going to spend all day distracted, daydreaming that she might tell me to go down on her tonight.
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Re: [cshorts] My (our) journey

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(Sunday 9 Feb)

Long foot rub this morning (these seem to now be running about 90 minutes). She then popped out to pee, and when she returned removed my cage. I had promised a neck rub next, but urged SL to lie back and spread her legs for oral — but I just teased. Got her heated up then stopped. She tried to keep me in there, and asked what was up, and I said I was just warming her up before neck rub, but that she was in charge and could order me to continue if she wished. She didn’t say anything, but rolled over for her neck rub (she woke up with a very tight, sore neck). After, we snuggled and made out for a little while, then she pulled me on top and between her legs.

After some more making out in that position I started to slide down to give lick her pussy, but she told me she just wanted intercourse today. I asked if I should use a condom to make it easier for me to last long and not cum — she said no, just see what happens, I could come or not, I wasn’t under any orders. I had in mind that I would hold back — it’s “only” been 5 weeks since my last orgasm. As I lubed her, I used the opportunity to slip in 2 then 3 fingers and play while she revved up her magic wand. She didn’t complain and within a few minutes she had a very strong, body quaking O. After she rested briefly, I slipped my cock in, and used it in one of her favorite ways: rapid, shallow thrusts just barely entering her, stimulating the muscles at the entrance of her vagina. As usual, that, along with her wand, sent her off another another grand climax. A few more minutes of resting, then began thrusting again, this time in about halfway, where I can best rub the head of my cock against her g spot. This was the biggest O for her yet, eyes rolling back in her head. I thought that might be it, but after a little I started moving slightly again to see if she wanted more. What she wanted was to send me off, apparently, because she started going ferociously after both my nipples, pulling and twisting and pinching them against my barbells. That almost always makes me lose control, and this time was no exception — after not too much longer I crossed the point of no return and had my own explosive orgasm. As seems to happen when she has denied me several weeks or more, the O went on and on, the spasms and ejaculation lasting longer than I’m used to. I collapsed in her arms, and after confirming that she was done, we snuggled for some time before rising for the day (the entire play session lasted 2.5 hours).
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Re: [cshorts] My (our) journey

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SL has been a bit more forthright about her desires recently -- I’m very grateful.

Today for example: we’re in LA on a mixed family (grandbaby care) and business (couple of meetings for me) trip. Time a bit flexible, fair bit of time working from our hotel room. Yesterday I was graced with providing both a wake-up and a goodnight “kiss” (oral ministration). This morning, though, after the early AM grandbaby duty I had to rush through my shower so I could get on a conference call. I apologized to SL that I couldn’t provide her wakeup kiss when I arrived back from grandbaby duty. She said “you can do that this afternoon when you get back from your meeting.” Sure enough, when I returned from my meeting in Santa Monica, she was sitting in bed reading and made it clear with her eyes that I had duties to perform. I stripped and started heading downtown, but then said “Oh, I have a bit of time, don’t need to rush a quickie, do you want to take it slow?” She looked me in the eye and said “No, get down there.” Yum. I *like* knowing I’m doing what she wants, whatever that is, and I especially like that she’s getting in touch with what she wants and feeling more comfortable about expressing it directly.

She’s also been getting much more specific about where she wants my tongue and fingers, and doing what, when I’m serving her. For example, she tends to want to climax more quickly than I naturally aim or: I try to go slow, build her up with more sexual tension. She’ll now grab my head and move me, pushing me so that my tongue is right smack on the nub of her clit, telling me in no uncertain terms to make her come fast and hard *now*. Hot!
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Re: [cshorts] My (our) journey

Post by Worrier »

Only read a few posts so far.. but this is wonderful. I love the joy you all have found in your relationships
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Re: [cshorts] My (our) journey

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(From 23 March)

Haven't written much in a while. Things have been pretty stable ... and slow, especially for me. I'm a bit down on how things have been going.

This morning's episode was one of the most extreme examples, but somewhat representative. After a slow build-up (with my reading erotica to her), SL got heated up, went to town with her wand and my fingers inside, and had a couple of explosive orgasms. Then (and only then), she spent I'm pretty sure less than two minutes playing with one of my nipples and gently stroking my caged cock, then stopped. She is fine with denial, and gets that I *want* to be teased, but much of the time doesn't put much into teasing me. The effort / attention in our play has always been quite one-sided: I've known this. I don't know that it occurred to me that this is somewhat problematic for trying to move things in a more kinky and fulfilling direction for me via chastity: a full-on T&D chastity (as opposed to just denial & humiliation chastity, which was never my desire) requires probably more effort than the pure vanilla relationship we had before. But, other than making some effort to accept and adapt to the chastity kink, if anything it seems like SL puts in less effort. I'm glad if she doesn't feel obligated to -- I never wanted sex to be quid pro quo, and I like about chastity that it's obviously it's not. But I was hoping that she would appreciate the power exchange and the freedom and that would make her want to engage more -- because she was having more fun.

She does seem to be having more fun -- certainly welcomes or asks for sexual attention a *lot* more, and orgasms many many more times a week. But, though she's experimented a little bit here and there with new types of attention, it's pretty much been one-and-done. She pegged me once (three months ago) and has shown no inclination since (despite my hinting -- clearly enough she definitely understood -- at least 2 or 3 times). She has slapped my bare ass a couple of times passing by, but nothing else (despite my asking her to experiment with thrashing me to tears). Used her wand on my caged cock once (maybe 5 months ago), then told me to leave it out (in my bedside table) and plugged in, but never used it again. All in all, she seems more selfish in taking her pleasure, while attending to mine less.

I'm working towards talking to her about this. It violates my mantra of "patience" -- letting things develop on their own -- so I'm not rushing to raise it. I have in mind initiating a talk around the 2-year anniversary of chastity (October). I've started taking notes of what's on my mind to help me prepare. I'm reminding myself to use "I" words, not "you" words.
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Re: [cshorts] My (our) journey

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I actually got punished (for the first time during sex) -- not funishment, but "I'm angry and this is serious." For asking too many checkpoint questions (like "are you sure?") which SL took as topping from the bottom (probably not incorrectly). Which means she was trying to be in charge, which is a good thing. The punishment means the current denial period is continuing (49 days so far).

We had a fun session: she definitely was giving me attention (I haven’t said or even hinted anything about this, despite the frustration I wrote about last week). After I gave her the by now standard Sunday morning hour-long footrub, I shaved her labia for her. She unlocked me and after some cuddling and increasingly passionate kissing she tore into my nipples. Recently she mentioned that she was always nervous about going too far with pain, but realized she never had reached my limit yet: today she was clearly pushing it further. I actually started to think about my safe word (which normally is never on my mind), though I wasn’t there. Instead, I had a powerful nipplegasm, and lay swooning for a while when she released me.

Then she wanted to insert a new prostate toy. It has a pretty elaborate shape (several bends and bumps, including external portion that wraps around the perineum) so she was unsure about how to insert it and had me show her, then turned on the vibrating plug in it. I started to roll over to go down on her, but she pushed me back and said she wanted to mount me ... and that’s what she did. She also told me she wanted me to have an orgasm. First violation: I asked if she was sure. I also asked if she wanted me to put on a condom to help me last longer since it had been many weeks, and also to help me not come if that’s what she wanted (second violation).

Some very lovely, very exciting PIV. However, for some reason I was not staying fully hard. Enough to stay in, but not filling her up and not letting me target her g-spot which I always do and she counts on. (Best guess is that I was too much in my head because of the frustration and unhappiness I expressed in my last entry). So, after some good but not over the top fun, she climbed off and let me know it was time for “second cock” -- her vixskin. I strapped on, she lay back, and things got *very* hot. She had two explosive Os -- the second one just kept going and going, her eyes rolling back into her head -- I’ve rarely seen her so transported. She collapsed after that, and I lay on her, nuzzling her breasts and gently kissing her lips. After she had recovered a bit, I slipped off the harness and slid my penis into her again. After a few gentle movements she began responding, quickly becoming quite enthusiastic. I was pretty much fully hard at this point, and able to hit her favorite spots. After she had another strong O, she said “I guess I wasn’t done!” A few minutes later I started gently trusting again, and she re-attacked my nipples ... generally a sure-fire way to get me to come (and a signal that this is what she wants, *now*). I started rising to my peak when I said “But I don’t deserve to come, I wasn’t hard enough for you earlier.” That’s when she’d had enough -- she shoved me off, and spent several minutes lecturing me, actually angry. She said I had to figure out what I wanted -- she was trying, but whenever she did I started pushing back with questions -- did I want her to take charge or not. I suggested that it is what I want, but that I’m learning too, and trying to break years of habits (which I think is true!). She calmed down...but my chance at an O was long gone!

It's baby steps (hence the long-term "patience" mantra for me). She said (again) that she's doing this for me -- she doesn't find it objectionable but the power exchange doesn't do anything for her. And it's (so far) about decisions on basics (e.g., am I going to have an O? If she says I am, I'm not supposed to ask "are you sure that's what you want?", fair enough). But the mere fact that she saw questions like that as challenging her authority, and didn't stand for it, I think is progress for us.
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