My Newfound Chastity

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A little about me, I’m a married 50-year-old bisexual whose bisexuality and interest in kink has come to the forefront. I can’t say it’s an obsession, but sex and kink are often all I think about. I’m a submissive oral bottom and in terms of my kink, I love CBT and electro both combined with some bondage. It doesn’t have to be pain per say, prolonged edging, milking, denial or ruined orgasm and post orgasm polishing are fine in my book.

I’ve been searching on several sites and received a chat message from a domme asking if I liked bondage, CBT and forced gay. I answered yes on all counts, but it must be physical play; I have no interest in any virtual relationship no matter how enticing the offer might be PLUS I won’t pay any “tributes” for playing. If this is workable, we can discuss further. Much to my surprise she was local and enjoys domineering men sexually just for the sheer enjoyment of it with one exception – before we could begin talking further, she needed to meet for coffee and that I would have to pay for this meet and greet.

A couple of messages were exchanged and we agreed to a date, time and location to meet. Imagine meeting at “The Leading Bird” for coffee and a chat. Don’t laugh, the Leading Bird is a real restaurant in town and serves a great breakfast although we were just going there for coffee. Anticipating our meeting, I was, to say the least, a bit wary and hesitant. I’ve been there before with my wife and kids, would anyone I know see me there or know the woman I was about to meet or worse, would they know why either of us were there? I talked myself into going or more likely it was my dick doing the thinking for me; either way, I was going to go.

A few days later and the morning came for our meeting over coffee. Gathering all my courage, I drove to the parking lot; I walked into the restaurant and looked around seeing my apparent domme in the far corner. I walked over to her and introduced myself as I was motioned to be seated. As we chatted, all my anxiety disappeared. She was a beautiful woman a little younger than I, maybe in her mid-40s. She explained that her husband passed away several years ago and she originally felt the loss of her husband but in time she also felt the need of kinky sex and intimacy she once shared with her husband. In coming to terms with her loss, she was comforted in knowing that her husband would not want her to forgo the FLR and FEMDOM lifestyle they both had enjoyed. She posted a profile on line and received several replies from potential partners. One by one they all fell by the wayside during online chatting and in only one other instance she had her meet and greet. She said it was a terrible meeting. It quickly ended and they parted company before the first cup of coffee was finished. She didn’t go into any details but I was pleased to make it this far.

She continued by saying she noticed my profile and that I sounded ok as a possible fit and that’s when she sent me my first message. Now that we’ve met, she’s happy that she reached out and now wanted to know more about me. Again, I told her that I’m happily married but have the need for kink which my wife doesn’t come anywhere near to satisfying. I’m not looking to have an affair with a woman, only kink; so, if she was looking for me to fuck her or sit on my face or similar, I’m not the guy for her. I repeated that I won’t pay for our play beyond this coffee.

She agreed right off and in response to her question, yes, my wife does know of my interest in kink, but no she doesn’t know to what extent or that I am seeking kink outside of marriage. I told her that I wish my wife had an interest in kink play of almost any sort, but I felt that that was not going to happen. I really enjoyed our give and take conversation over several cups of coffee. As my cock grew hard in my pants, she painted a picture in very broad strokes of what my life as a submissive would be with her. After more give and take and in the end, we agreed that we’d meet for our mutual interest in kink. I was to address her as Mistress Rachael, never look her in the eye and I would be referred to as her little boy or some other derogatory term. Before we did however, she instructed me to purchase three items and to message her when I have them. First is a chastity cage that it must be appropriately sized adding there’s nothing worse than a cage that’s too big. Second item is a butt plug that’s approximately the size as my dick and the third is a set of clover-type nipple clamps.

Amazon delivered my items and I immediately messaged my Mistress Rachael. She was pleased with how quickly I obtained all items. I was then ordered to get used to them: lock myself in the cock cage, insert the butt plug and apply the nipple clamps. Do this daily for the next week keeping each item on for as long as I could tolerate it. Take a picture the first time and send her a message each subsequent day of how long each was applied. The cock cage went on rather easily and isn’t too big, butt plug was a little rough going bahçelievler escort in the first time and got easier each successive day. It was the same for the nipple clamps and I learned the very first day that removing the nipple clamps hurt more than when they’re first applied.

Mistress Rachael was pleased that I followed her instructions so well and a time was arranged to me to arrive at her home. But that I would have to have all three items on for my drive over. When I arrived, I was instructed to park in front of the garage and call her. The drive over thankfully was an uneventful quick 15 minutes from my house. Turing off the roadway, I entered the winding driveway and proceeded to the garage and parked as instructed. Before me was a nice size house located on a rather private-looking piece of property.

I then called Mistress Rachael and was instructed to get out of my car and undress completely leaving all clothing items in the car. I was allowed only to carry with me my cell phone, car keys and the key to my chastity cage. Then I was to proceed to the front door and ring the bell.

The property wasn’t quite as private as I originally thought as I nervously undressed and walked to the front door as Mistress instructed me. As I approached the door, I recognized the Ring doorbell and I realized that I was now visible to anyone who was looking. I rang the doorbell and a voice came from the speaker, “Turn around and face the roadway” it said. I could see the cars driving by and wondered who was able to see me. The voice then instructed me to walk past my car and around the house to the patio in rear of the house. On the patio I would find a table and, on the table, a small lock-box where I would place my cell phone, car and chastity cage keys and then lock the box shut. Next to the box there would be a collar that I was to put on, lock attach the two chains on the collar to my clover clamps and then wait for further instructions.

I can’t explain how uncomfortable and vulnerable I felt undressing on the driveway and leaving all my clothes in the locked car. As I walked to the front door and then around to the back of the house, in broad daylight, I was naked expect to the chastity cage, nipple clamps and butt plug.

I quickly walked to the rear of the house and toward the patio. I saw the table and box and collar. I placed both keys and my phone in the box and locked it shut and then attached the collar around my neck and small chains to my clover clamps. And here I waited and waited for what seemed like a long time. Fortunately, the weather was good and the sun felt warm on my naked skin. As I waited, I felt very vulnerable and ill-at-ease on multiple levels, first I was naked at essentially a stranger’s house with all my clothes locked in my car, I was caged and plugged with nipple clamps, my car keys and cell phone were locked away and the collar I just locked around my neck had a very heavy chain attached to it that was anchored to the patio. At this point, I couldn’t leave if I wanted to.

After what seemed like a long time, Mistress Rachael exited the house and walked towards me saying, “Hello and welcome to my home.” She then proceeded to adjust or should I say tighten the collar some.

“Stand still” she said, “now, turn around, let me look at you. You’re very attractive naked and rather fit for being 50. Thank you for following all of your instructions. I will be your Mistress Rachael; you will always address me that way and I will call you boy or whatever derogatory term suits me at the time. You will be my submissive. Understood?”

I replied with a simple, “Yes, I do Mistress Rachael, thank you.”

Now that you’re here, tell me your name and why you’re here asked my Mistress.

Yes Mistress, I am Tom Adams and I am here to be your submissive and you will be my Mistress.

Are you here voluntarily, Tom?

Yes, Mistress I am here voluntarily.

I fidgeted some as she touched my clamped nipples and caressed my cock and balls and felt for the butt plug in my ass.

Tell me about yourself and of your family life.

As you know Mistress Rachael, I am married and we have three grown sons and six grandchildren.

More, please Tom.

I felt ill-at-ease with her questions, but, at the same time, compelled to answers Mistress’ questions fully and completely. I told her everything she asked about me and then some, where I lived and worked, all my contact information, my family, our sex life, how and why I turned bisexual and my greatest, yet deepest sexual desires and fantasies including how I wish my wife would share in my kink interests or more correctly take total control of my sex life in an FLR being her submissive.

Now that it was over, having told Mistress everything, I felt strangely at ease with myself. What was once hidden, maybe even from myself, was now in the open; at least to a her.

As I told you before, we will both have fun and fulfil each other’s physical, bala escort sexual and mental needs in our relationship; my needs will always be paramount and my orders obeyed she said. Mistress disconnected the heavy chain from my collar and attached a leash and proceeded to walk away with me in close pursuit behind. As we walked, “This is my garden; I love being outdoors enjoying my garden and all its colors, beauty and smells. I hope you don’t have allergies because I plan to spend a great deal of time outside with you.”

Replying, “It is lovely Mistress and no I don’t have any allergies.” It was indeed a beautiful garden and obviously professionally designed and cared for, full of flowering plantings, a seating area, a pergola with a swinging seat and small fire pit.

“That’s ‘Mistress Rachael’!” she barked. “You mentioned that you were an exhibitionist at heart. How did you enjoy your naked walk from your car to my front door and then to the backyard?” I bet you wished that people were watching you the whole time, didn’t you?”

“Yes, Mistress Rachael. I found the walk exciting and yes, despite being a bit scared and intimidated, I wish others could have seen me” I said.

“So, you are a willing and eager exhibitionist, are you?” she quipped.

“Yes, Mistress Rachael, I am. I enjoy being naked. I am comfortable with my body and not ashamed to be seen naked.”

“Around other people, strangers and even those you might know, like your neighbors?”

“Yes, Mistress Rachael, I enjoy being naked around other people even those I might know; but I don’t know my neighbors in this context and can’t very well be naked outside the house where they’re looking at me.” I replied.

Mistress replies, “It’s so nice to hear that you enjoy being naked and on display around other people. I You know that my late husband and I had a circle of kink friends, maybe some of them are your neighbors. I bet you would enjoy any form of sex too in the open for others to see as well.

Continuing, my neighbors and select friends will surely like to meet you. You see, over the years, we have played together with my late husband and me; they’re such a lot of fun to be with. Roxanne and Rod are my next-door neighbors. Roxanne leads their FLR; she will enjoy you to the extent I let her. I think you’ll enjoy her husband Ron especially; he’s bisexual and will do whatever his wife or I direct of him. I know he prefers to top, so your mouth and ass will need to satisfy him; YOU will also be the only sex he gets. Don’t worry my little boy, you’ll still get to take my various dildos and other toys in your holes. Enough said, let your Mistress Rachael take you inside and show you my playroom.”

With me still at the end of her leash, Mistress Rachael leads the way into the house. From the patio we enter a gourmet-style kitchen and great room. Around the corner are the stairs that lead to the basement. Descending the stairs there’s a small “anteroom” at the bottom with a chair and a coatrack. There’s also a door that leads to what Mistress Rachael tells me is her playroom or what others in the BDSM world would call a dungeon. Mistress Rachael’s face lights up as she describes all of her toys and accessories that fully equip her dungeon. She informs me that we could play in the dungeon for weeks and never have the same experience twice. She describes much of her dungeon equipment including the sling suspended from the tall ceiling, a milking machine, a fucking machine, several estim power boxes, several racks, tables, chairs, benches, crosses, stocks, a cage and chains and other things hanging from the walls and ceiling and an open wash(ing) area. Mistress grabs for my cock and says, “I feel your cock trapped in its cage trying to get hard, it’s obvious your cock likes what it sees.

In a conversational tone, Mistress Rachael informs me that I will soon meet her neighbors Roxanne and Rod. “You will address Roxanne as Miss Roxanne and Rod is just Rod” says Mistress Rachael in a very authoritative tone of voice. Continuing, “Rod used to be a real sexual bull, but like many bulls, they are only interested in their pleasure. Miss Roxanne has changed his whole personality and now, he is normally just a chaste fuck toy just as you are. Nothing done this afternoon will be anything more than what you said you wanted most. Any questions?”

“No Mistress Rachael” was all I could muster but with a million questions going through my mind.

As I stood in the middle of Mistress’ dungeon naked but for my cock cage, butt plug, collar and nipple clamps, in walks two people I’ve never seen before. Mistress Rachael introduces me to her neighbors Miss Roxanne and Rod and then instructs me to kiss Miss Roxanne’s shoes. Both are fully clothed and I’d say both Miss Roxanne and Rod are in their mid-30s; she’s quite attractive and he appears to be rather muscular. After what seems like a very long time, I am then instructed by Miss Roxanne to stand and remove Rod’s clothes. Removing Rod’s shirt, balgat escort I notice that he too is wearing a collar. Unbuckling his pants and pulling them down, I get my first sight of Rod’s cock locked in a cage. Rod’s cage is at least twice the size of mine and fills it completely. Miss Roxanne speaks for the first time repeating something that Mistress Rachael told me about Rod, the ONLY sex that Rod gets will be with me and I am to obey him.

Yes Miss Roxanne, I reply.

Miss Roxanne hands me a key and orders me to remove the cage from Rod. His cock is completely flaccid now and it looks beautiful. It’s probably twice the size of mine as it begins to get hard as I work the retaining ring from around his cock and balls. I can only imagine what awaits me with Rod’s massive cock.

Mistress Rachael orders Rod to take me to the wash area and clean out my ass. The wash area is an open tiled area with a sink, toilet, some hoses and a floor drain. Ro tdells me to remove my butt plug, sit on the toilet and go to the bathroom. I’m mortified, if being naked wasn’t enough, here I am going to the bathroom in front of three strangers.

When I finish, “Stand up” he commands, inserts a hose in my ass, tells me to sit back down and turns on the water. Almost immediately it feels if I’m going to burst as the water fills my bowels. The pressure alone forces the hose from my ass with the water and all else emptying from my bowels in to the toilet. This is repeated several times before he announces to Mistress Rachel that I am ready. I dry off with the towel hanging from a hook on the wall.

We walk to where Mistress and Miss Roxanne are. Well Tom, are you ready to have your wishes come true? they ask.

“Yes, Mistress Rachael and Miss Roxanne I am ready” I say.

“Tell me again Tom, what is it that you want” Mistress Rachael asks.

“I would like Mistress to do as she wishes with me; to be fucked and pegged and my balls milked dry.” I say in reply.

“Nicely said Tom” says Mistress as she frees me from my cage and the pain is sharp and excruciating as Mistress removes my nipple clamps. But before we start in earnest, I think you and Rod need to get to know each other a little better. And with this Mistress attaches a short chain between our two collars leaving us face to face. “Go ahead and kiss, I want to see deep passionate kissing. Make love to the other’s mouth.”

I’ve never kissed a guy before, but this experience was electrifying. Never have I felt the excitement and passion of a kiss like this; it was like I was making out for the first time in my life. Oh, how hard our two cocks were and when they touched, it only added to my heightened arousal. With the way Ron was kissing me back, he was enjoying our kissing as much as I was. His full erection was proof of his excitement.

When our marathon kissing session was ordered over, Miss Roxanne removed the chain holding Rod and me together.

“Tom, get on your knees and take Rod’s cock in your mouth and suck. Rod, do not cum.” Miss Roxanne ordered.

I did as instructed in taking Rod’s cock into my mouth and began to suck. It was huge and was all I could do to get most of it in my mouth before gagging. Mistress Rachael told me to stop, get up on the “table” and lie face up. The table, was nothing like I’ve ever seen before. As soon as I was positioned correctly on the table, Rod strapped me down, waist, legs, arms and chest. Rod then made several adjustments to the table where he separated and elevated my legs as if in stirrups and the section supporting my head was lowered.

“Well Tom,” Mistress Rachael began, “Time for the fun to begin. I suspect you remember me telling you that you will be the only sex that Rod gets, right? And before I could speak a word, “Well, no matter, Tom,” Miss Roxanne continued, “you will pleasure Rod by allowing him to fuck your face. Be sure to get his big cock nice and wet so that he can then fuck your ass. Yes, that’s right, you are Rod’s only sex and he’ll make good use of you today. And after he cums in your ass, Miss Roxanne and I will take turns pegging your ass all the while this vacuum pump will continuously suck and milk your cock and balls. This pump won’t stop and will eventually empty your balls of their cum. Thereafter, any orgasm you have will be dry as your balls are empty. I suspect you’ll be screaming for us to stop your torment long before your balls are empty, but we won’t hear you with the ball gag in your mouth. Are you ready Tom?”

“Yes, Mistress Rachael, I am ready for all that you have planned for me.”

My words just left my mouth when Rod slid in his still hard cock into my mouth. He was easy on me at first, but fairly quickly began to facefuck me balls deep. I gagged and couldn’t breathe, but he would slide out some allowing me to catch my breath only to be gagged and choked again as he slid in balls deep. He pinched and twisted my already sore nipples. When Rod had enough fun fucking my face he moved to between my raised legs and put his dick against my hole and began to press. Fortunately, between my spit on his dick and me somewhat pre-lubed, he forced his entry. The pressure was unreal, little by little until his entire 8″ dick was in my ass — balls deep; it was then the vacuum pump was placed over my dick and turned on.

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