Crowe's story: 20 years so far

After many years, I've finally decided to start a journal about all my ups and downs. I'm not going to start with one long ass post covering everything from beginning until current time, so be patient, this has been 20 years in the making. I'll start of by saying that I've never been into the sissy or slave/ mistress scene. I lead a normal life, you know, going to work every day, yardwork, camping, fishing, hunting, ect. We don't do the "serve her every need and she does nothing" life, we both work full time, take care of the house, and have kids at home. It's not the exciting "leather and latex in the dungeon" life like some might be living, but this is my story.

 

We'll start with the beginning. I remember having an interest in bondage at an early age. I'm not sure how I got interested, because back in the 80's there was no internet and I was too young to go to the nudie book store, but I always got a bit of a thrill seeing women tied up in movies and such. Fast forward until the age of 18 or so. I started dating a girl that was wanting to experiment with being tied up and such. Both of us were pretty inexperienced, but we still had fun. I had a good friend at the time, Jenn, that I could tell anything to, and I would openly talk to her about bondage and she would give me ideas on what I could try. Jenn was the more "experimental" one of the group. Cute, piercings, hair always different colors, and she was only into girls, which is why I always felt comfortable talking about things with her. Sometimes she would show up at my place with different things for me to try with my girlfriend, gags, nipple clamps, restraints. Well, things didn't work out with the girlfriend, and I was pretty down about it for a while. Jenn had come over and said that she's tired of seeing me all moping around and she had something in mind. She had me strip down to my undies, which I was perfectly comfortable doing with her since we'd swam in her pool in our undies on multiple occasions. What I didn't expect was her to bind me to the chair, gag me, and rip my boxers off of me. I had always thought that I was supposed to be in charge of all situations. This was something different, something I kinda liked. She had also stripped. She rubbed her body all over me, teasing me like I've never experienced in my life! I remember that she rubbed her pussy and ass over my cock and said something like "don't get any ideas, I'm not into dick". At some point, she tipped the chair back onto the floor with me still bound to it, straddled my face and said "today you start learning what a woman really wants". This was my first time being bound, first time licking a woman, and first time that I felt alive.

 

We would have other times like this. She would tease me and only allowing me to cum by my own hand. She would have me go down on her every time we were together. She always said that it wasn't for her enjoyment because she was a lesbian. She said "face is face and all I'm doing is teaching you". I knew better. I knew that each time I went down on her, she would instruct me on exactly what she needed to get off. This went on for several months until I moved 3 hours away for work. We would still get together anytime I came back home to visit. I started dating a new girl after a while, so my time with Jenn has started to diminish. My new girlfriend was a bit dominant and loved the skills I learned from my mentor.

 

Things with Jill, my new girlfriend, were going great. I've never had a girlfriend that was dominant like she was. It wasn't anything over the top, more times than not, she'd prefer to have me tied up while we fucked and fooled around, but wasn't at all the fantasy mistress in leather thing. We were just a couple of horny 20 year olds having fun. It was different than what I had with my Jenn. Jenn was a genuinely loving person, Jill was more about fucking and didn't really show much emotion. Jill understood the relationship I had with Jenn, we were partners in crime for a lot of years and still talked on the phone a couple times a week. Jenn asked when she was going to finally meet this "mystery girl", so I suggested to Jill that we take a weekend trip back to my home town and she can meet some of my family and friends. We came back for a weekend and finally got to introduce Jenn and Jill. They seemed to hit it off right away, which made me pretty happy. The only thing that I did notice was that Jenn seemed a little jealous, which is not like her. A couple days later, as Jill and I got ready to drive home, Jenn gave me a hug and whispered to me "Call me when you get home. Private conversation. I love you, Timmy Boy." I thought about what she said and why she said that the whole drive home.

 

On the drive home, I talked to Jill about our weekend and what she thought about my friends and family, especially Jenn. She said everyone was pretty cool and could see why I have a thing for Jenn. She knows about everything with Jenn and I, so I said something along the lines of "Yeah, she is really special to me. She's been one of my best friends since 1992 or so." We talked all sorts of things on our drive just to keep my mind off of what Jenn wants to talk about privately. I dropped Jill off at her apartment and told her that I was just going to head home and relax after our weekend before I had to work in the morning, then immediately got home and called Jenn. Expecting the worst, I dialed her number and waited.... "Timmayyyy!" She always did that when we called "I like the new chick. You guys seem pretty happy together. " I said "I am, but I'm not sure... Sometimes I kinda feel disconnected from her". "Well maybe you just need a little Jenn-bug still in your life, you know, for balance. That and you can probably use a little more training, if ya catch my drift." I knew she missed me and I was missing her, but not much I could do now living 3 hours away, a girlfriend, and Jenn not interested in dick. "You think Jill would be cool if you and I still got together once in a while?" That's something I'd have to talk to her about. After we got off the phone, I thought about it. 3 hours isn't that far. Every other weekend back home, back to familiarity, and most of all, back to eating my Jenn's pussy! It was a gamble I was willing to take. Take the chance of giving up what I have with Jill, the bondage, the fucking, the fun for my friend that doesn't fuck but makes me all giddy after all these years? I thought about for a few days then finally said something to Jill about it. Jill asked if that meant that we would be breaking up. I said that would be up to her, but I didn't want to. She thought for a little while and said "I want to talk to Jenn before I make any decisions. I know she's into girls and all, but I don't want you fucking her and falling in love and leaving me". "You know how I feel about her already, and you also know about the type of relationship I have with her. Not once would she even fuck me in all these years." "I still want to talk to her about it first. Maybe set up some rules. I'm not saying no, but I'm not saying yes. Can you have her give me a call sometime?" I called Jenn the next day and told her that Jill wanted to talk about the situation first. I kinda knew that either way, I would go back and see Jenn.

 

They talked on the phone for a while and laid down some rules. First rule, no fucking between Jenn and I, only oral. Jill said that was fair because Jenn taught me so well and there's always room for improvement. I wasn't allowed to cum while I was with Jenn, that was what Jill was for. And the final rule was that Jill could tell me no Jenn time at any point. I was living a dream! If I could only go back to those days. Over the next couple of months, we only got together 2 or 3 times. It was always such a long drive and I also didn't want to feel like I was neglecting Jill. I was starting to fall in love with her as we spent more and more time together. The company I worked for at the time had just announced that our location will be closing and we would be out of jobs within the next 90 days. Jill suggested that we move in together, to which I upped the ante and said "Let's move to my home town." She thought it was a great idea. This is going to be great! I'll be living with my girlfriend and be back with my best friend! We both found jobs right away and an apartment. Jenn was thrilled that we were all going to be within 20 minutes of each other. The first month back was busy. Buying furniture, unpacking, getting settled in. Jenn and Jill started getting close. Jenn would take her around town to show her the way around, go shopping together lunches,. Then one morning while I was at work it happened. My phone rang and it was Jill. Something happened. Jenn was on her way home the night before from work and was in an accident. I could hear in Jill's voice that it wasn't good. All I remember her saying is "Jenn's gone" What! No! This has gotta be a bad dream! It wasn't. I was in a haze for the weeks following. I couldn't focus on daily life and quit my job. Jill was trying her best to be there for me, but I just shut down. It took me a couple months for me to start getting back to normal. This new normal sucks but there was nothing I could do to change it.

 

October 21, 2002. One of the worst days of my life. I still think about her often.

 

As time went on, things got better. I was lucky enough to get my job back, my boss there understood the grief I was going through. Things with Jill were a little strained. She would want to have play time, but I wasn't very interested in fucking or anything. Finally one night she said "You're going to get out of this funk and I'm the one that's going to do it." She told me to close my eyes and open my mouth. She popped something into my mouth and told me to swallow, then open again. When I did, she stuck something on my tongue. Something I haven't had in quite a while, 2 hits of acid. Oh boy! This night is going to get crazy! I asked what it was that I swallowed and she said Cialis. "Pretty soon you're going to be tripping balls and have a raging boner that I'm going to ride for the next 2 days" Looking back, that was kinda what I needed, to get my drive back, have fun again, to smile again, to get back to living. Still, I wasn't too interested in fucking. Jill said one time that she might have figured out why... When I was with Jenn, I would get teased for hours and never cum, then when it came to have time with Jill, I would be so worked up that we would fuck like rabbits. She had a plan, we would have play time but not have me cum for a week at a time. Sometimes it worked, sometimes we would go a little too far, sometimes I couldn't take it and just take care of myself in the shower. She seemed to notice when I did because maybe I wasn't as worked up as I should have been. One night we were surfing the internet and came across a site that sold bondage gear and other toys. Up til now, we both only knew of gags, restraints, and the usual "normal" toys. There was something that we saw that neither of us had seen before, a chastity cage. She said something like "That might keep you from beating off when you're not supposed to" I laughed a little and we moved on. A few weeks went by, and I thought about what she said and this device we saw on the site. It was a bit expensive for what it was, around $200 for this plastic cock cage. There weren't a whole lot of options for cages back then, and I said fuck it, it's only money, so I ordered it. It took about a month to arrive, and when it did, I immediately slipped off the the bedroom and tried it on. Fiddling around with the different sized rings, spacers and pins, I finally got a combination that fit. I would wear it around for a few hours at a time, making adjustments to the different parts until I was most comfortable and getting used to it. Finally, I was to maximum comfort (looking back it was the most uncomfortable hunk of plastic I could ever wear) and it was time for the reveal to Jill. We went away to some cheap motel for a night, mainly to swim in a in some shitty pool that everyone in the tri state area probably pissed in. Anyways, we were in our room and she was in the shower rinsing off the pissy pool water and chlorine mix and I put my new cage on and locked the little padlock. I put the key on the bed next to me and waited for her to come out. She came out drying her hair, talking about dinner plans or something, not really paying attention, then her eyes just fixed on my little plastic prison. "What the fuck!" Shit! This isn't the reaction I was hoping for! "I, uh, ummm....." was all I could manage to say. "I really didn't think you'd buy one. How's it feel?" "Different. And a little weird. You want me to take it off? We can forget all about this." "No, let me get a better look. Yeah, it's a little weird, but let's give it a try for a little bit and see." Ok, that wasn't as bad as it could have gone. "Wanna fool around?" I said. "Not really, not much you can do with it now anyways. How about if we run down to the bar for a couple drinks." That wasn't really a question, but more of a "this is what we're doing" comment. I went for the key to take off the cage and she said "just leave it on. This might be kinda hot!" We went and had a few drinks and a couple hours later returned to our room, both of us a little tipsy.

 

Thanks. A piece at a time is the only way I can tell my story, otherwise it would be one long ass post. This spans from late 90's when I was introduced to kink until current time. Bear with me.

 

I'll try for paragraphs... It's already bad enough typing on this little ass screen

 

When we got back into the room, I had all these ideas running through my head of the kinky time we were going to have. She was going to tie me up, do all sorts of things with me, tease me and who knows what else. Nope. Instead we got into an argument over something she said "Just take that thing off. I'm not interested now." I took it off and we spent the rest of our romantic night away in an awkward silence. I ended up sleeping in one of those uncomfortable motel chairs using my coat as a blanket.
The next morning, I woke early because sleeping in a chair all night wasn't really pleasant, and went to the lobby and got myself a coffee and sat outside for a smoke, thinking about the events from the past night. I came to the conclusion that maybe this whole cage thing was a bad idea, so after about an hour, I returned to the room. Jill greeted me with a half smile and a "Good morning sunshine." I kinda smiled back and replied simply with "Yeah, morning." She asked what was wrong, like nothing was wrong. I told her what I was thinking while I was outside, that maybe this was a stupid idea and that I'm just ready to go home. We got all packed up and headed out. Our drive home was only going to be about an hour, but it was going to feel a lot longer to me.
It was only about 15 minutes into our ride home when she said that it wasn't stupid, just that we were both a little drunk, and that we should give it another shot. I said "Ok, but next time we'll not drive an hour just to get drunk and fight." Agreed. Next weekend will be a chance at redemption. We got home, unpacked, and just spent the last few hours of our Sunday evening just watching TV.
All week I thought about what our upcoming weekend was going to be. Was it going to be all hot and passionate? Would we try the cage again? Would we get into another fight? It was a long week, but Friday was finally here, and when I got home from work, Jill was waiting for me on the couch. "Get showered and get your thing on." I hurried in the shower and put my cage on and went to the living room. "Show me" was all she said, so I dropped my towel. She gave it a quick look and then pointed to her pussy. "Lick" to which I immediately got down on the floor and went to work. My cock strained in it's little plastic prison while as I licked her fiercely.
After she came, I was kind of expecting that she'd have me take the cage off. Nope, she said it was staying on all weekend. It was tight and uncomfortable, but it was also something that I initiated. We, or shall I say, she had a great time, me going down on her several times over the course of the weekend, and me, balls aching and having to constantly fidgeting with ball ring. Sunday night, she said I can take it off. Thank God! I had pinch marks in places that I never would have wanted. It was also not the freshest feeling in the world, not really knowing how to keep things clean for this first "long" lockup. After I showered and we went to bed I told her about my issues and that I wasn't sure I wanted to do it again. Jill said "Nonsense! This was a fun weekend! You just need to get used to it and we'll see how it goes from there."

 

We kept on trying with that uncomfortable hunk of plastic for a couple months with minimal success on anything longer than a couple days at a time. I came home from work one night, and there was something on the kitchen counter. A little black velvet bag with a tag tied to it. "Just a little something for you" was what the tag said. I opened it up and it was a new cage! A nice new shiny metal tube with bars at the end. It looked a little intimidating compared to that plastic piece of shit we've been trying. It was a little tough getting my balls through the ring and even tougher getting my cock into the tube, but eventually got it in. As I went to line everything up and put the lock on, I noticed that it fit much snugger and shorter than the previous cage. I clicked the lock shut and admired my new cock.

When Jill got home she said "All right, let's see it. I know you already have it on" so I dropped my shorts. "Fucking A yeah! That's what I'm talking about!" Apparently she really liked the promise of a more security and long term. "How's it feel?" Surprisingly well! "Good because no matter what, you're in that for a week." "A week? What if you want to take it off?" "It'll have to be in a week. Did you see any keys with that new lock? I mailed the keys to my sister back home and told her to drop them in the mail on Monday. I didn't tell her what was in the envelope, so don't worry." I guess I'm stuck for a week now. That scared me a bit, but yet really turned me on.
We fooled around every night for that week and I was really feeling the effects of the smaller cage. Finally the keys arrived. "You ready to be set free?" "Actually, no. This has been the hottest week ever!" "You haven't seen anything yet.... You just wait." I stayed in that cage nonstop for 2 more weeks. We had lots of her teasing me and me giving her lots of oral. We took a little break from the cage for about a month and I'd completely forgotten about what she said about "I haven't seen anything yet ".
We played with chastity off and on, doing different things, but one that really sticks in my mind was when Jill brought up bondage along with chastity. Hell yes! She had me strip completely and put my cage on. She asked if I had a safe word I wanted to use, and I excitingly said No. "Suit yourself. I'm not going to play nice." I didn't care, I was just thinking about how much fun this is going to be. "Arms to your sides and stand still." She began wrapping my chest in cling wrap, working down to my hips and back up several times. She then had me lay on our coffee table "Legs together" I complied and she continued with the cling wrap down my legs and over my feet. The only parts that were left exposed was my head and my caged cock. "Open that bitch mouth of yours" and in went a large ring gag, holding my mouth wide open. "And now for the top". Jill then began to wrap my head and put a couple pieces of aquarium tubing into my nose. She left my mouth accessable then strapped a funnel to my gag.

 

This was the most helpless I have ever been. I was a bit nervous and excited at the same time. I couldn't see anything, I couldn't say anything, and I sure as hell couldn't move. I remember feeling Jill's hands running up and down my body and lightly touching my balls, and it made me shiver a bit. She whispered in my ear saying things like "How fun is this?, I own you now, and you don't know what you're in for".
I felt her fiddle around with my cage, then a cool breeze and she uncaged my cock. She teased me, alternating between her fingers, pussy, and mouth. Shit! This was fucking amazing! She had me so close to cumming so many times and knew exactly when to stop. I felt her moving over top of me, then something was poured into the funnel. Little splashes of cold water. "Very good, let's see if you can handle a little more" then came more water, this time it was one quick gush. I managed to swallow it all in one gulp. "Impressive, let's try a little more"
I felt more movement, and then her mouth lightly on the head of my cock. Her weight shifted back, and then another rather large gush into my gag, only this time it wasn't water. Warm piss filled my mouth and I had no other option than to swallow it. I heard he laughing, almost manically as I swallowed and then she smacked my balls. I almost forgot all about the piss because of the pain. My hard on went completely away with that smack and then the cage slipping on immediately. She turned her body around and must've been masturbating over me judging by her sounds and movements.
After she got herself off, she removed my gag. Then slowly she cut off the wrapping, starting at my feet and moved her way up, leaving only my arms still bound. "That was fun! Don't you agree?" She grabbed me by my cheeks and had me mouth the word "yes". "Good! Would you like to do this again?" This time I voluntary said yes. I don't know what had gotten into her, but this was kinda hot and a little scary.

 

Before anyone starts thinking " Boy, does this guy have a lot of kinky shit going on" it's not like that. Most days were the usual day to day life, the boring stuff that nobody really wants to hear about. I'm just recollecting the times that are most memorable to me. Our play time might be a couple of weeks or even months apart.
With that said, we did have a replay of that fun night, just this time with a little more. Jill had been telling me for a few weeks that I'm "gonna get it" but when would be a mystery. I had been outside for a while working on something, not quite sure what I was doing, but I remember that we were expecting a bunch of snow that night. When I came in, Jill said I should go take a nice long shower to warm up and by the time I got out she'd have dinner ready. I thought nothing of it and took my shower and when I was done, man was dinner ready! There she was, all stretched out on the couch in some little red crotchless panties and matching cupless bra.
I went for it and was told no, I can look but can't touch. She did however let me get a little sniff, and then told me to lay on the coffee table. She pulled a couple rolls of cling wrap from under the couch and said "You know what to do, arms down" and then, just like last time, wrapped my arms to my side, stopping just at my hips, then upward, again with the tubes in my nose so I could breathe and the ring gag in my mouth. This time she told me to stand and placed a collar around my neck then led me down the hall to the bedroom. We had installed a couple of eye bolts into the ceiling joists shortly after we moved in, she tied the collar off, then pulled it tight but left a little slack.
"I've got another surprise for you" she said as I felt her secure a cuff around each of my ankles. This must've been been why she didn't wrap lower than my hips. She then kicked my feet apart. "Just a little more" then she put a bar between my ankles and clipped it to the cuffs. "Oh one more thing" she said, then put that funnel into the gag. Here I am, bound gagged, collared, and drooling. At least my cock was still free. Wrong, the cage went on next. " Don't go anywhere, I have to get one more thing."
I'm guessing that about 15 minutes pass before I hear the door open. "Here he is! Just like I told you!" Who is Jill talking to? "Tim, I'd like you to meet Nicole from work. I needed a little help with this next part. Don't worry, she knows what she's doing." What?!?! She brought someone here to see me in this predicament? I felt a couple hands touching all over me, my chest, back, ass face, cock, all of me. "Oh, he looks like he's ready for some fun. Too bad he's not going to like it though". Then one of them smacked my ass, hard, and I let out a yelp through my gag. ""Oh, we gotta do something about this!" then all of the sudden it became hard to breathe. There was a new, different scent coming through the tubes and I could almost taste it in the gag. Nicole had stuffed her panties into the funnel to shut their "fun boy" up.
What followed next hurt like hell! Both of them were beating my ass with what felt like wooden planks. This continues for what felt like days, but in reality was probably 10 minutes. My ass hurt and they didn't care. "Let's see what else he can take" Jill then said "I don't know, I guess we'll find out" What the fuck did that mean?! Oh, I soon found out. Something cool and slimy right down the ass crack, then something pressing against it. I felt like I was going to tear in half it hurt so damn bad, then all of a sudden, pop! Whatever it was is now sucked into my ass. My asshole burned, but the inside felt really good.
"Damn, bitch! First try! You sure he's never done this before?" "Nope, total ass virgin." "Let's see if he does as good with the other side. Take that thing off his dick and let me see what I got to work with." Jill took my cage off and then I felt what I'm pretty sure are Nicole's hands stroking my cock and squeezing my balls. That's when I felt the same cold slimy feeling on the tip of my dick, then came the pressure. "Deep breath, it won't be that bad " Nicole said. There was something now trying to make way into my piss hole. It went way in, all the way, then I felt the pressure inside. Did she really just stick a catheter in me? Yes she did. "You're going to be like this awhile and don't need you pissing all over the floor when you gotta go." I did find out that Nicole was a nurse where Jill worked and did in fact know what she was doing.

 

There i was, totally helpless at the hands of my girlfriend and her co worker, gagged with some strangers panties, a plug in my ass, and now a tube in my piss hole. I was humiliated but also really turned on. What did these 2 have in store for me? My mind was all over the place. Safe word, what was the safe word? Not that I'm in any position to speak. Fuck! We never used one! It was usually just some innocent playtime between Jill and I, but now there's some strange girl involved and I'm really in over my head this time.
The panties were removed from my gag and my head pulled back. "Drink." What's it going to be this time? It turns out it's something I like, Gatorade. "You need to stay hydrated. You're in for a very long night" Every so often one of them would pour a little Gatorade into the funnel, leave the room, then come back to check on me. After what I'm guessing was about an hour, I still didn't feel like I had to pee, so good call on the catheter, ladies.
"He's looking about ready." I felt a little tug on my piss tube, then my head pulled back and a large splash of piss....my piss. I tried to fight it and blow it back out or my gag which earned me a hard slap in the face. "You fucked up, mister!". A few minutes later, something else is poured into my gag. It tasted like a mix of hot sauce and horseradish. It was fucking terrible! My mouth was on fire! "Now I bet he'll drink it. Anything to get rid of the burn." Next came another splash of piss. I held it in my mouth as long as I could before swallowing. ""Good job bitch? Here comes more!" Then it was a constant pour of my piss into my gag. As soon as I swallowed the last bit, I felt a tugging on the catheter again.
They left me for a while by myself and went to the living room where I could hear them laughing and some music playing loud. I have no idea how long I was in this situation. I was getting tired and my legs were really starting to ache. Every so often, one would check on me, patting my balls or wiggling the plug in my ass. Jill came in at one point and said "Nope, he hasn't filled it yet." I think she was talking about my piss bag. That probably moved them on to plan B, using their own piss.
"Fresh from the tap!" As my head was pulled back and a nonstop supply of piss entered my mouth. "Yeah bitch! Keep going! There's plenty to go around!" I heard Nicole saying and they're both laughing their asses off. It felt like I drank a gallon. Within maybe an hour, I must have passed everything from my bladder and into the bag. They both seemed pleased when they came in this time. I felt that tug again, and without warning, another round of piss. This time I didn't resist. After I finished it off, I felt the pressure inside start to subside as the catheter was removed. My cock hurts, but apparently I was pretty aroused by the whole thing, I didn't want to be, but I was.
The funnel was removed, but the ring stayed in place. One of them was behind me and began to wiggle the plug around and then slowly pulled it most of the way out, then pushed it back in, over and over. I let out a moan and sigh. Why was I enjoying this? It doesn't matter, I was. The wrapping was cut off but my collar and spreader bar stayed. As my eyes adjusted, I saw Nicole for the first time. She was cute. About 5'1", short black hair, tattoos, and a lip ring. The sight of both of them is something that I still picture, Nicole topless in some little black boyshorts, and Jill towering over her in some 4 inch heels, which made her over 6 feet.