Boundgasm

My spouse, Mistress, and keyholder took me to a kinky party yesterday, but left me in chastity. However, I was luckier than another guy we saw there.

It’s been over 5 weeks since my last orgasm, and 23 days of continuous lock-up in my JailBird + PA-lock. Last night, though, I watched a poor guy get teased to an unbelievable degree — and he’s been denied orgasms for 57 days.

His owner had bound him (naked of course) to a suspended leather sling with plastic wrap in the dungeon at this party. She then proceeded to sexually tease him for a solid hour, stroking his cock and stopping before he could orgasm. A small audience watched.

If he got too close, she would give him some “distracting pain” to “help” him avoid an orgasm. Things like slapping the head of his cock really hard with her hand, or grabbing his balls and squeezing them hard. He got close to cumming time after time after time. But he never spurted.

I’m not sure what their agreement was, but he was begging not to orgasm. In the end he got his wish, but not before what seemed like an unbearable amount of substantial penile stimulation. His owner knew how to get him off, her hand-job technique was clearly effective. He was hard the whole time, and making the most interesting noises throughout.

His scene was still going on when Mistress decided it was time for me to submit to her and our friend. She took out our lightest leather bondage hood and secured it tightly around my head. It has a snap-on blindfold and a snap-in gag, which she left out initially.

She led me over to a bondage table, with webbing for dozens of straps to bind the limbs and torso. I’d been on it before, and knew what to do. I removed my clothes and got in position to be tied down.

Mistress kept it simple, using just 5 of the thick nylon straps to secure my wrists, ankles, and waist. Our friend joined us, and I was then blindfolded and gagged. They wasted no time and started tickling me mercilessly. I recognized the voice of the owner of the other chaste male who was tickling my feet and really enjoying watching me thrash and squirm and (try to) yell. Mistress and our friend were at my sides tickling my ribs. I felt completely out of control as my body tried uselessly to move away from the excessive stimulation. They all seemed to have a great time.

Eventually they stopped, and Mistress directed our friend to help calm me down with “smoothing” hand motions on my skin. My breathing slowed, and I settled down.

Then I felt her start stimulating my nipples. Mistress whispered to me that she wanted me to orgasm in front of everyone in our new special way. I nodded to let her know I understood and would try. At this point we’ve only done it a few times, and I wasn’t sure I could do it there in the dungeon. But, wanting to please her, I was going to try.

The nipple stimulation continued, and I continued my deep breathing, focusing not on my cock but on the growing sense of sexuality throughout my body. My cock doesn’t get very hard during these experiences — it’s not a penis-based orgasm. I felt the sensual energy building inside of me.

Then she was biting me. Mistress’ teeth dug into the flesh of my chest as her fingers continued their very arousing motions on my nipples. Then our friend began biting me on the other side, and licking my nipple as she sucked my breast skin into her mouth. The pain mixes with the pleasure for me, taking me deeper and farther.

I heard Mistress ask me if I needed more, and I nodded. The two of them continued stimulating me and biting, until finally I went over the edge. My body shuddered and I felt flushed. I strained against my bonds as I tried to arch my back and spread my legs as the orgasm spread through me. They continued stimulating me and pushing me on, until I went limp. Mistress reminded me to continue breathing as I recovered.

I wasn’t sure what to expect at the party, but it was a very nice scene. Mistress seems very interested in exploring this alternate way of pleasure for me, and she continues to show no interest in my cock. I think it’s her way of encouraging my new female sexuality to emerge.

A number of people seemed surprised when I got undressed before the scene. But I wasn’t sure if that’s because they didn’t realize I was a guy (I was wearing a new hot dress for the party), or if they hadn’t seen a stainless steel chastity cage like mine before. Either way, I was fully on display for quite a while. Being blindfolded, I have no idea who was watching during our scene.

A short while later I was dressed again, fetching Mistress some food and then massaging her feet as she chatted with others. A little while later we were back in the dungeon watching several other scenes, while I was Mistress’ footstool. It was a wonderful evening.

Cooked Bool Tincture

I wrote Mistress yesterday, confessing a concern/desire I’ve been thinking about:  CBT.

Potentially I won’t even have my cock and balls in as few as 15 month (after surgery to become a female). And as a male submissive, CBT is a pretty typical thing to experience. I realized that I haven’t experienced much along those lines though. And time is, literally, running out.

So I wrote Mistress an email about this, how I felt, and that I wanted to simply leave the issue in her hands. What she does when, if anything, how intense, etc, is all (of course) completely up to her.

Well, this weekend is one of our BDSM play parties. She told me today she’s already talked with a friend to help her with a scene she has planned for me. This friend is very much into pain herself, and is well versed in kinky things of all kinds. I’m a bit frightened to consider that I might just get what I’ve asked for.

Then again, Mistress may have something entirely different in mind. I won’t know. One thing I do know that she has planned is for me to come out as a transsexual to our friends at the party. I’m not worried about that at all, there are lots of transgendered folks in our kink community.

I only asked for one thing specifically: a butterfly board experience. The link is not for the squeamish. Of course if/when that happens is up to her.

We’ll see what she has in mind for me tomorrow night…

500

Saturday was quite a special day, both for my wife/keyholder/mistress and for me. Her birthday was that weekend, and she decided that I would receive birthday spankings on her behalf. Rather than use her age, she set a high goal for me to earn release from chastity and an orgasm: 500 spanks.

With her help we made a little progress towards that during the week: 15. Only 485 spankings to go.

On Saturday we attended a play party with friends. This was a kinky party at a friend’s house in their BDSM dungeon. About 30 people attended. I picked up a Byerly’s birthday cake that was decorated with roses. I asked them to customize the frosting with her name, and to add thorns to the rose stems, which they did.

After we arrived at the party, my wife suggested that I let people know about my predicament. Most folks I asked were happy to help out by spanking my ass. So with my pants at my ankles and my CB-3000 visible, I received scores of birthday spankings. Most used a nice leather paddle that my wife prefers (similar to this but red). However, a few used their bare hands. Before very long I had over 300 and was pretty sore and pink.

Soon a special friend arrived at the party. I had phoned R earlier and asked her to participate in a special scene that my wife had wished for. A short while later the three of us were on the dungeon floor, where R and I stripped and laid down next to each other. My wife put on gloves and proceeded to fist us both at the same time. I was still locked in chastity, but during this scene R had three orgasms. My wife/mistress loved having one hand inside R’s pussy and the other inside my ass.

After that scene we cleaned up and then mingled with our friends some more. I asked for additional spankings. My wife said I had to stop at 480 so she could take over. I suspected she might quit at 499 and leave me locked up for the night. Indeed, at that point she administered the next 19 herself and stopped. I begged and pleaded for one more. To my surprise, she layed into my red rear with one more hard one, bringing my total to 500.

I asked to be unlocked, and she instructed me to retrieve the key from her keyring and ask someone else to unlock me. As it turns out, the couple who introduced my wife and I to each other were at the party, and I asked him to unlock me. He was happy to, as I suspected he might be, since he is also locked up at times. He knew what it meant for me to get unlocked.

Back in the dungeon, my wife had me strip again and lay in a leather sex sling with my legs up (like this but without the ropes). Apparently my orgasm would be here in front of everyone watching. She whispered something to R, who disappeared for a short while. My wife produced our largest dildo (similar to this), ready with a condom and lube. She held it at her waist and started fucking my ass with it. Due to it’s size, this is a very intense experience for me.

R returned and my wife asked her to masturbate me at the same time. A minute later my wife told me to close my eyes, turn my head, and open my mouth. I did so, and someone shoved their cock down my throat. He grabbed my hair and proceeded to fuck my face. I can’t do justice to how amazing this was – to be simultaneously used at both ends and jerked off. With so many sensations going it, it took me a few minutes to focus on the orgasm that was building. But before long I came and came and came. Having been locked up for a week, it was a wonderful orgasm, and the additional penetrations made it even more intense and incredible.

I opened my eyes and recognized D, a substantial presence in the local scene, as he took his cock out of my mouth. We both laughed, since I had sort of owed him this for a while. About a year ago I was crossdressed at another party here. Sitting in his lap, I got him all turned on but then had to run to a scene when my mistress called. Since then he had teased me about “finishing the job”.

Of course I’m locked back up now. My wife has been very appreciative of the dual fisting scene I helped arrange for her. And I’ve been so grateful to her, not only to have had an orgasm, but to have realized such an incredible fantasy with her. We are both aware of how fortunate we are to be together.

Songbroke

She finally broke me. As I wrote in my Violation and Transpotential posts, my wife/keyholder was not going to let me have another orgasm until I sang a song that I did not want to sing. She was willing to keep me locked up for 5 weeks before allowing me a release without singing it.

I gave in on Sunday. Coming to bed that evening she sexually teased me for a while, stimulating my nipples which makes me so horny. But the CB-3000 locked on me keeps my cock under 3.5 inches, pointed down, and small. It’s torture for me, and she enjoys it a lot. This went on for about 20 minutes, which can seem like hours to me as I writhe and desperately crave some genital stimulation.

She stopped and said she wanted Tiny (her name for my cock) and his house (the chastity cage) between her legs. I moved into position, essentially missionary, and gently pressed the cage against her pussy. She started grinding herself against it, and directed me about how much pressure she wanted. It was indescribably difficult to have my cock so close to her opening and feel nothing. She, on the other hand, was easily working herself towards a substantial orgasm.

I was aware of my cock pressing very hard against the inside of the solid plastic enclosure. It felt like the cage might burst open from the pressure, but it didn’t give, and my pulsing cock and balls ached so very much with each throb. I watched her slowly reach her climax. I felt genuinely and deeply honored to be providing her that pleasure, yet I could barely stand the pain radiating from my own genitals.

We then cuddled as she relaxed and floated in the afterglow of her orgasm. After a while she took my head and thrust my face into her armpit. I was surprised, but she smelled really good. Not perfume, but a natural scent of her own that pushed my arousal level through the roof. It was more than I could bear. I could not stand the sexual intensity for even one more minute. I caved in, and said that I would sing the song if I could please, please, please be allowed to orgasm.

She stopped, and was a little surprised. “Really? You’ll sing the song?” I consented, and begged to be allowed to orgasm inside her. She asked why. “It would feel so incredibly good to feel you, your pussy feels so wonderful and it feels like it has been forever. Please may I cum inside you, please Mistress?” I had no self respect left at all, the only thing that mattered was doing what she wanted in order to earn myself some sexual relief.

“Very well,” she said, “get Tiny unlocked. And since it’s going inside me, wash that skanky thing.” I threw on my robe and hurried downstairs to retrieve the key from her keyring and unlock myself. After a quick washing of my genitals, I was back upstairs and in bed. I felt so sexually activated, so fully aware of the urgent need for her body next to my body. It was more than just needing to cum, I needed to touch her, hold her, smell her, and feel her next to me.

I gently and sensuously attacked her, attending respectfully to her breasts, her lips, her thighs, feeling her hair between my fingers, smelling her deeply. It felt very close to what some would call a peak experience. I slowly entered her and savored the feeling of her warmth and wetness wrapping around my cock, which was finally fully hard after a week of captivity. I took my time and honored both of us, drinking in the sensations everywhere on my body. Even so, it still only took me a few minutes to climax.

But it was glorious. It was incredible. It felt so beyond words. I laid there and held her, and thanked her, and felt so in love and appreciative. What an amazing woman, to bring me to such a thrilling experience. Time was irrelevant as we lay together.

After a while we talked a bit, and she made it clear that she wanted me locked right back up in the morning. I agreed. It seems likely it will be at least another week of lockup for me. Saturday we have a play party, and she is really looking forward to it. It’s her birthday weekend, and guess who will be receiving her birthday spankings?

Getaway2

After giving her an underwater oral orgasm in our hotel room jacuzzi (see prior post), she informed me of her kinky plans for the evening. “I want you to think up a scene for me. And maybe, just maybe, you’ll be able to earn yourself an orgasm.” I was all ears!

She explained: “You’re going to put on a show for me, and it needs to contain the following elements: bondage, self-inflicted pain, and edge-play.” I thought about this for a while, and had some questions, mostly about the edge play. She explained that it wasn’t about masturbation edging, but about working with an emotional boundary for myself. The goal was for me to come up with something that was near a limit or edge for me, and to push that limit in the scene.

She explained that if, in her opinion, I achieved the goals and she enjoyed it sufficiently, I would be permitted an orgasm. I asked about her participation, and she said that I needed to manage all the details myself, but that she would be willing to make herself available to a minor extent. She didn’t want to know any specifics. So as we lingered in the hot tub for a while longer, I pondered my options and came up with something I thought might just earn me that orgasm.

Eventually she decided we were done in the jacuzzi, so we got out and dried off. She went to the bed and started reading a book she had brought. I gathered our play bags in the “entertaining area” of the suite, by the couch which was out of her sight. I retrieved a set of things from our bags, and began to prepare. I moved the coffee table away from the couch to make room for me to on the floor at the foot of the couch.

She loves white rope, so I started by using that to tie off one testicle. Wrapping the rope behind my back and around to the front again, I tied off the other testicle, and cinched the rope behind me so my balls were pulled apart. I used another rope to wind tight around my cock, from the base up to the head, and then tied that off tight. I pulled the dangling end between my legs and knotted that to the rope in the small of my back which forced my cock down and severely back. Before long my bound genitals were aching noticably.

With more white rope I bound my knees together. I put leather cuffs on my wrists, and a leather collar around my neck with it’s O-ring in the back. We have two nipple clamps connected by a chain, and I tied a rope in the middle of the chain (for her to pull, as needed). I used one more white rope through my collar O-ring to each of my big toes, pulling my feet behind my back. I applied the nipple clamps to my nipples. The last step was to latch the wrist cuffs together behind my back.

I called out “I’m ready Mistress.” She put down her book, came over to the couch, and sat down. I told her “I know you like foot worship, but we’ve never done it because it’s not my thing. Tonight that will change. Please pull on this rope if I am not pleasing you adequately.” That rope would not only pull on the nipple clamps, but make them tighter too. She smiled. My balls, cock and nipples already were hurting, and we hadn’t even started.

She picked up the rope and tested it. Then she sat back on the couch and put her foot in my face. I opened my mouth and she inserted her big toe. “Suck it,” she said. I tried, but she yanked on the rope causing significant nipple pain and I yelped. “Be careful with the teeth!” she directed. I sucked her toe more carefully. She inserted her other toes in my mouth, repeated with the other foot, and rubbed her feet across my face. I wasn’t sure what to do. Sometimes I licked or tried to suck, other times I just let her feet explore my face.

After a while she felt the scene was complete. She checked in, and my pain was approaching my limit. She quickly removed both nipple clamps at once, which spiked that pain to about 13 out of 10. She chastised me for making too much noise, and rubbed my nipples as if that would help. Instead it maintained their pain level at about 9. “Thank you, Mistress.”

I was still bound, and next she went to untie my genitals. My balls were <i>extremely</i> sensitive, and her long nails were like pins. She untied first one testicle and then the other – and they each surged with renewed pain as blood flow and feeling returned to them. The tenderness of my cock was thankfully trivial compared to what my nipples and balls had just been through.

As I de-bondaged myself, we talked about the scene. She was very happy with it, and felt it satisfied her requirements. However, she did feel that we needed to find a true foot fetishist so that I could learn how to properly worship her feet. Her play with my nipples throughout the rest of the evening revisited pain, rather than my usual sexual response. The following morning I cashed in the orgasm she granted me by masturbating.

So, all in all we had a fabulous getaway together. And again, this is not a fantasy, this was what really happened.

I’m back in “verbal chastity” again, not even stimulating myself a little bit without her explicit permission.

Parlors

It has been 4 days since my last orgasm, and 14 days total that my cock has been under her control.

I have a pretty similar story for the events of last night: about 20 minutes or so of solid nipple stimulation, making me ultra horny without being able to get hard or obtain any pleasure at all. My wife/keyholder seems to enjoy it though, so that’s all that matters, right? I still wonder if this “nipple training” of hers is actually training my cock (and mind and body) to learn that it’s pointless to try to get an erection when aroused. If so, then are these teasing games of her actually bringing about the uselessness of my cock that she humiliates me with? Seems like a possible mind fuck there.

You may recall that I sent her info about a chastity accessory that might increase security. She noticed that the KSD-G3 add-on was for the CB-6000, and they don’t fit the CB-3000. The KSD-G2 is the one for the chastity device I wear, and I’m even less convinced about that one helping to eliminate the pull-out potential for me. On second thought, the KSD-G2 might make reinsertion impossible, so maybe it would be worth a try?

I got a call back from the piercing parlor we always go to, and they want to do a consultation before making any recommendations about new piercings for me. They want to see the scar tissue from my past healed holes as well as what flesh they have to work with in order to assess the likelihood of any future piercings being rejected. They also gave me a recommendation for another place that will do tattoos on the penis, since none of their current artists do those.

I called that other tattoo place, and they also said they need a consultation before proceeding or quoting prices. I shared all this with my wife. I’m not sure what her plans are. Maybe she will ask me to schedule a consultation about piercings, or the tattoo, or both; or maybe she will do the scheduling. I’m sure she would love humiliating me by telling the tattoo artist that she wants “tiny” permanently inked on the head of my cock. Or would she get more enjoyment out of watching me describe the details while she is there?

I also suspect that the consultation wouldn’t be the end of it. Knowing her, she’d want to go forward with it right then, assuming there were no concerns from the tattoo professional. Then again, maybe she’d schedule it for some time in the future to torture me for longer due to the anticipation. I really am worried about how much a tattoo will hurt on the tip of my penis. I’ve read that topical anesthetic is not something that tattoo parlors can legally do due to medical regulations. So I’m not sure what options we have left there, besides unbearable pain for me (which my wife would probably really enjoy, so I guess I’m screwed there).

Adjacency

Last night my wife pleasured herself by using me in a particularly humiliating way. I’m still locked in the CB-3000 with no relief in sight, but that doesn’t prevent her from achieving sexual satisfaction.

Wearing only a light top to bed, she laid next to me, spread her legs, and rubbed her hands sensuously all around her genital area. She wanted to get my attention, and she succeeded. I asked her if I could please give her some pleasure. She laughed and said “How? With that pathetically small cock of yours? That’s never going to happen. What I need is a Real Cock.” I agreed, responding “Yes Ma’am, you deserve pleasure from a good sized cock, not my worthless and tiny thing.”

She continued stroking herself while I watched her. I craved so much to smell or taste her. She grabbed my head and moved it so my face was inches from her pussy, ordering me not to move. She spread her labia lips, massaged her sex, and put on a show that made me ache inside the confines of my plastic penis prison.

I begged to lick her. She said no, and continued to manipulate and stimulate herself in front of me. She was clearly getting off on teasing me and knowing the pain she was indirectly inflicting on my genitals. After a little while she said that I may lick her once, but only once. I slowly ran my tongue from the bottom to the top of her pussy, savoring each brief second.

Then she pushed my head away and told me to put Tiny up next to her opening. I asked her if she wanted me unlocked first. She laughed again, saying “Hell no, why would I do that? Keep your useless dick locked and get that thing over here.” I complied, putting the rounded end of the CB-3000 next to her warm, moist opening.

She grabbed my nipples and pulled them towards her, using them to direct the amount of pressure that my chastity device applied to her clit and vulva. She slowly started grinding her pelvis against the plastic encasing my cock. My straining cock would have been touching her wet vagina, if not for the chastity device which completely prevented me from feeling anything at all.

She was clearly getting closer to an orgasm, and continued to direct my position and intensity with her firm grip on my nipples. Her roughness with them made it clear that she was more focused on her approaching orgasm than being careful about the pain she was inflicting on me. Soon she cursed me for making it more difficult for her to cum, and she increased her efforts. Shortly thereafter she gasped and climaxed, releasing my aching nipples and pushing me away.

I laid next to her and cuddled as she relaxed in the afterglow. My genitals were throbbing, but they had not been stimulated in the least. It was strange that my cock felt so intensely unsatisfied, while my wife lay next to me in complete sexual satisfaction. I felt wholly objectified, merely used for her pleasure, a toy for her amusement and hedonism. It felt strangely wonderful and right.

After a short while she directed me to give her a back rub as she went to sleep. I felt a deep ache in my balls for quite some time as I massaged her shoulder and back muscles. Soon she was asleep, and I carefully rolled over next to her. I thought to myself: this is what it means to be a male in chastity. I felt extremely frustrated sexually, yet somewhat fulfilled.

Today I accomplished quite a few things around the house that seemed like they might count in my favor in her eyes. She even mentioned the possibility of a release for me as a reward. But that could just be a tease. It hasn’t even been a week. Then again, I have no idea what her plans are for me now.

Partway through the day I could see she was growing troubled with several life issues that have been weighing on her recently. We talked, and I listened and was as supportive as I could be. However, it looked to me that her concerns would likely be elsewhere tonight. It seems unlikely that she’ll have much energy or interest in anything as relatively low priority as my blue balls.

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