(This story is completely fictional. I wrote it just for fun so the events and characters in this story are not real.)
**[Part 1] (https://www.reddit.com/r/Erotica/comments/yucllv/fictionalf26m26fpovchastity_becoming_a_keyholder/)** / **[Part 2](https://www.reddit.com/r/Erotica/comments/yucmm4/fictionalf26m26fpovchastity_becoming_a_keyholder/)** / **[Part 3](https://www.reddit.com/r/Erotica/comments/yuz3ag/fictionalf26m26fpovchastity_becoming_a_keyholder/)**
Much like my previous entry, I am going to jump ahead in time once more. You’re probably wondering how long I left Owen in chastity with the cliffhanger in my last post and to answer that plainly, I don’t really remember as his chastity timings got a bit sporadic and vague after this point. I will explain why.
To let the cat out the bag, me and Owen got together not long after that fateful night of his month long chastity. Like, boyfriend and girlfriend together. Basically what happened was on one of the weekends when we would see each other I went around his apartment to chill and hang out as we would normally do, but I accidently fell asleep on his couch and he didn’t wake me up so I could go home at a normal time and by the time I woke up, it was nearly 2am. There was no point in going home so late at night so he let me stay over. He offered me his bed, but I refused it and he refused to sleep in his bed because he wanted me to take it (both of us showing our stubborn sides) so we ended up sleeping on the couch together. However before we slept, we drowsily pillow talked and ended up talking about our feelings for each other. Turns out, when you regularly spend lots of time with a person, flirt and help them to achieve orgasm, you eventually begin to grow large and powerful feelings for them. Love is typically what it is called. We made out a little and then cuddled to sleep on the couch. I can’t help but smile and blush thinking back on this specific night, since I am writing all this in a past tense, I won’t comment on whether or not me and Owen stayed together at this point as that might spoil future parts. Just know, I was overjoyed to have him as my boyfriend at this stage.
So the relationship brought a new dynamic between us as well as our comfortability of keyholding since we had been doing it for nearly 2 months. The rules from past parts were still in place, but we were a lot more flexible on them. The time lengths between each sentence were more up on my own interpretation rather than a set time for release. Porn consumption was similar. Sometimes I let him indulge himself and others I made him abstain. This is why I have chosen to skip ahead quite a lot because a lot of his releases during the next few months were on a whim and fairly similar to his previous ones. Either letting him jerk off or giving him very minimal physical touching or visuals to allow him to cum before he was placed back in his cage. I would say the time difference between the last part and this one was around 2-3 months.
The reason this part is worthy of its own entry is because Owen’s birthday was coming up. His 27th. Our relationship was only getting stronger and we were having lots of fun with the keyholding and every aspect of our relationship. Anyway, this was his birthday and such an occasion deserves a little more reward than any other time of the year. I never let him in on too much of what I planned to give him but I was always scheming and plotting what I could do to tease and keep things fresh with us. As much as I could be fairly cruel and dominant with him when it came to the sexual side of us, I did love him and genuinely believed he deserved the best on his birthday so I intended for this to be nothing but a good day for him.
I had made it a regular thing to stay at Owen’s place. I had my own home but I didn’t live by myself so in classic girlfriend fashion, my stuff has been slowly transferring over to his place, making it easier and easier to stay at his. He, of course, did not mind this transition. This meant I awoke at his side on his birthday. “Happy birthday sweetie!” I said groggily pulling him in for a fresh morning breath kiss. We idly chatted for a little while, avoiding the chilly air outside of the bed until Owen made the first move and left the warmth of my arms and the bed covers. This was the usual routine and for a reason, at this point (3 months into our relationship) Owen still had not seen me naked and we had not even had sex yet. By normal standards, some people might say this was an incredibly slow relationship. We shared a bed, a living space and I often saw him naked and helped him cum somewhat regularly. So what gives? Was I shy or I didn’t trust him? The answer is nope! My skin had sort of become a teasing weapon against him in chastity. When he was deep into his imprisonment, even the sight of my shoulders or legs could drive him wild and the touch of my freshly shaven thighs was enough to make him struggle and strain against his cage. My cleavage was a reminder of his key in my posession. All of these things were significant on the sexual side of our relationship and I didn’t want to lose that. I made routine checks with him to make sure he was comfortable with this and he always responded positively saying he was fine with it. One of the main reasons he always gave me when I asked this was that chastity was his main kink and the point of chastity is… Well no sex or release till a specific time. He never felt I was holding back or being frigid. He actually liked it was going at a slower pace and I was the same.
Anyway, this meant he usually was the one that left the bed first and got ready for the day ahead. I usually wore a t-shirt and either shorts or pyjama trousers to bed so even if I did have to get out of bed, he wouldn’t see my nude form but we just got in the habit of him leaving first so there was less chance of him accidently catching me naked. This started to occur after he walked back into the bedroom while I had just finished putting my underwear on after a shower, this was the most nude he had seen me to this date, and he felt bad as I never gave him permission to see it (such a good sub he is) I didn’t mind that he saw me in this way as it was a complete accident and there wasn’t any following punishment for it, but we slowly worked out a way so he never accidently saw more than he should.
After we had both got ready for the day and some openings of presents he had got from myself and his family, I gave him his final present for the rest of the day. I removed his chastity cage. He’d been in chastity for around 2 weeks on the day of his birthday and I felt it was appropriate to allow him a day of freedom on it. I did tell him he wasn’t allowed to cum till the evening so it wasn’t complete freedom, though he didn’t have to wear his cage throughout the day. It was a work day so unfortunately I couldn’t tease him much in person albeit I made sure to send him a selfie or two in the day as an extra treat. For me, the day was somewhat slow, mostly clock watching as I waited it out till more celebrations for my lover’s birthday. I am unsure how the day was for him, probably just as long.
The evening came and I had made a booking at a nice, local steak restaurant for us to dine out at. I pulled out a dark red pencil dress I had not worn in quite a few years, it still fitted me perfectly and with a slightly fuller face of makeup than usual (nothing crazy but I made an extra effort with my lips by putting on red lipstick) I was ready to wine and dine. The dress showed my shoulders and it stopped just before my knees. I also made sure to adorn the key necklace I always wore around him. Even though he wasn’t wearing his cage, it was still a great accessory to have near my cleavage if he looked and this dress offered a decent amount of it. When I stepped out of the room ready to go, Owen saw me and he could not help himself instantly complimenting me with a “Wow…” and “You look absolutely stunning!” as he approached me and swiftly put his lips to mine. I obviously could not resist similar temptations with him looking as suave as he did and we made out for a few minutes. We stopped when I felt a certain growth against my thigh, something I was not used to feeling as he would usually be in his cage. I playfully ordered him to “put that thing down.” And to sort out his now slightly redder lips, which had been stained by my lipstick. I also had to fix my lips before we left since they had been smudged.
The meal we shared at the lovely establishment was delightful and beautiful. Perfectly made to our order and we were full of chatter as the night grew older. That was something that was great with us, conversation flowed smoothly and there was no such thing as an awkward silence. The content of the conversation we shared will remain between me and Owen, but just know it was a happy occasion. I’ll also share that I did the vintage rub of his legs with my foot under the table trick a few times as we awaited our next course. By the end of the meal though, we were full and satisfied. I paid for the whole meal, it was my treat of course, and we left for home.
We held each other by the waist as we walked, the restaurant was about 30-40 minutes away by foot depending on your speed and we weren’t in any rush to start with. It was somewhat busy out and about, it was a weekday so it was mostly people returning home or going from place to place. Continuing my teasing as we walked, I squeezed his butt a few times through his trousers. He wasn’t allowed to touch my butt and he held his temptation and returned it by just squeezing my hip. We giggled at each little poke or prod at the retrospective areas on each other’s body before I quickly leaned and pushed him into a gap between 2 stores, sort of like an alleyway but it just led to the back of the stores I believe. I immediately started kissing him, having to get on my tiptoes a bit, but still I kissed my man. I was infatuated with him and this was definitely a loving outburst from me. An affectionate explosion as I kissed him multiple times and layered it with “I love yous.” Owen replied in the similar fashion both in words and actions before I slowed down, biting his bottom lip a final time and staring deep into his eyes before speaking.
“I’m going to make you feel good tonight.”
With that, I pulled him out of the gap by his wrist and we walked at a brisker pace than before. When we got back to his apartment, we kissed and giggled a few more times before I put my metaphorical Mistress hat on and ordered him. “Stand naked in the bedroom, no towels.” He obeyed and as you can imagine, it didn’t take long either. I walked into the very sight I asked for except he was wearing a very eager smile on his face. I was still wearing my pencil dress and makeup, the only difference being my hair was now in a tight ponytail and I was holding a piece of fabric in my hands. I approached him and stood in front.
“Do you trust me?”
“I do Mistress.” He replied.
“Do you *blindly* trust me?”
He went to respond as I wrapped the piece of dark thick fabric around his eyes and tied a knot behind his head. His response just became a chuckle.
“I repeat, do you blindly trust me? Are you comfortable with this?” I asked softly.
“I do Mistress and I am comfortable.” He responded putting his hand behind his back in habit of how I always ask him to be when getting his release.
“Good.” Was all I said next as I lightly ran my finger down the middle of his chest. I tested the blindfold’s effectiveness before stepping back. I pretended to slap and hit his face a few times to see if he would flinch. He did not. I took a brief second to admire his form before I dropped down to my knees in front of him, a familiar sight for me though this would be the first time I would do what I did. His penis was semi erect already and I brushed the underside of it with the outer side of my finger to help it grow to its full state. My usual procedure and once it got hard, I took my finger back. I planted a soft kiss on his lower stomach and let out a soft and gentle exhale.
One final sensual stare at his pulsing cock before I committed to my plan. I laid out my tongue and gave it a few long licks on its underside, the same place my finger just stroked. Owen softly exclaimed at the wet feeling and the original smile he had grown a little larger. As my licks reached the apex I offered his frenulum some extra, more delicate licks before fully encasing his tip in my mouth. A sudden, slightly salty sensation striked my taste buds as his pre cum lathered my tongue and my mouth adjusted to accommodate this first time meeting.
“Oh my go…” Owen whispered into the room.
I went slow, gently bobbing my head up and down across his tip. With each motion, I would delve a little further down his shaft and in turn, his tip got wetter and slipperier both from my spit and his pre cum. I rested my hands gently on his thighs for support and I got into a rhythm making sure my neck was consistently pulling and pushing my head. I moaned gently as soft, wet sounds escaped my lips, my eyes closed trying to get lost in this act of pleasure giving and to focus on my technique. I wanted this to be good. I wanted this to be perfect. My tongue wagged and licked at what it could, always trying to catch the edge of his glans. My lips created a warm closure and always seeked to go further and further down his cock. It wasn’t long before I started to feel his tip approach and tickle the start of my throat. I knew I could take him all the way and made one quick dive down. I rapidly felt it slide down.
“Ohhh Mistress… Mistre..!!” Owen blurted as he felt it. His legs buckled slightly and I needed to grip a little harder on his thighs to keep steady.
After this point, it was relatively easy for me. I could retract and push my head up and down his sodden pole, more wet and slick noises filling the room as spit lightly dribbled down my chin. As I made attempts for breath, I still licked and flicked with my tongue across his tip. I was orally pleasing the man I loved with such passion and devotion. This was long overdue for his returned love and loyalty to me. I have no idea how long this lasted, I was in a trance and only focused on the job at hand (or mouth in this case), the only thing that pulled me out was the sound of Owen’s voice.
“I’m close Mistress! I’m so close!!”
“Cum then.” Was all I thought in my head as I delved deep to deepthroat the man I loved once more. Owen called out some more before he reached the point of no return and it wasn’t too long before I felt the warm, salty juice shoot on the back of my tongue and throat. Everything about him twitched. His voice, his legs, his balls and his cock in my mouth as multiple ropes filled the sides of my mouth before I even had time to swallow the previous amount. He was able to fully finish inside my mouth and it took me a few rounds of swallowing to completely deal with the amount he gave me. I earnestly did so though and I provided a few more licks and sucks to ensure he was spent, although there were still a few more globs that came out, which I swallowed all the same.
After I was satisfied with my work, I took his slowly retiring penis out of my mouth for the first time since I started. I stood up with the ever so slight salty aftertaste in my mouth apparent after receiving my creamy dessert of the night. Owen’s face was one of relief and elation once I faced him, he was still blindfolded though.
“Tha… Thank you Mistress.” He spoke hearing my stand.
I moved myself to his right side, my mouth close to his ear so I could whisper my next words gently into his ear.
“That was from your girlfriend, not your Mistress. I love you very much and I hope you have had the best birthday. Don’t take off your blindfold till you hear the door close behind me. Clean yourself up and we can cuddle and watch a film when you’re ready.”
“Yes of course, I love you too.” He whispered back.
I eskimo kissed him on the cheek. I was unsure if he was comfortable with me kissing him after giving him head, but my nose tickled his cheek and I smiled at him one final time before leaving the room.
I know some people may feel this was ‘just a blowjob’ but for us it was definitely a big jump from basic touches and teasing to me actually giving him sexual pleasure with my body. It’s hard to explain, but for us, that was a huge moment especially for me because I was openly giving a part of myself to him as an act of love and compassion. When we started, we were doing it just for the fun of the kink. Now, we were doing it because of love.
(Hope you enjoyed this development between these two! Thanks for all the supportive comments in the other parts! Glad you are all enjoying these stories. Any feedback, criticism or comments are welcome below or in DMs!)
Source: reddit.com/r/Erotica/comments/yw5fgl/fictionalf26m27fpovchastityoral_becoming_a