Years after having had my world turned upside down and discovering just how far over the edge I really could go, my world would be turned upside down again. After having discovered the whole new world of being made a cuckold, I would find myself being made a cuckold again. I would like to say that my college experience with Jessica and having been so properly indoctrinated into the world of Cuckoldry, I would just chalk it up to college experimentation and go on to date and have relationships that were more along the lines of the social norm. However, that is just not how life goes, I guess. After Jessica and I went our separate ways after college I was left feeling rather unsure of myself, dating, and women in general. Were all women secretly like this, or most, was this some deep dark desire that women have but rarely live out? these questions plagued my thoughts and mind for quite a while.

In the years after college and Jessica, I made attempts to date women and not approach the topic of previous relationships or kinks as I being a young man was unsure of how that would be received. How would they react? Would they judge, call me a homo, or freak out and think I was some weird freak? Needless to say, I did not have too many successful relationships immediately after having left college and the life I had. I allowed too many questions to consume my thoughts, fears, and insecurity. I went out on a great deal of first and second dates but not much further than that for years. As the years passed, I became rather complacent with being single. I began to feel that being single, alone, and unattached was just how my life was heading. Mind you I grew up thinking and wanting so badly to someday find my one true love and get married, have kids, and all that jazz. I so greatly dreamed of this often. Just wish to one day be half the husband and father that my father was. Needless to say, here I am just having turned forty-three earlier this year and I am single never married and have no children. I have plenty of nephews and maybe that is just the way things were meant to be for me.

It was probably about eleven years ago I met a girl that still to this day I have the utmost weakness for. Kate and I met at a dog park of all places. I instantly was blown away by not just her appearance but the general glow of her personality. Let me preface this by saying I am a huge fan of Rachel McAdams everything about her and the characters she plays. Kate as it would be looks amazingly like Rachel McAdams which never dawned on me at first. Kate was 4’-10” maybe 4’-11” and has a cute little booty and full B-cup-sized breasts.

So, Kate and I hit it off splendidly. We talked and spent a lot of time hanging out there at the park and had moved on to hanging out some outside of taking our dogs to the dog park. As luck would have it though, Kate had a boyfriend so things kind of just fizzled out. Kate and I loosely kept in touch over time and about five years later we got back into communicating more and eventually began to see one another more. Kate unbeknownst to me had some issues going on that I didn't realize. She had a bit of an addiction issue and was not the most reliable person or kind of flakey, I guess. I took the flakey behavior and inability to be reliable as a sign of disinterest and we kind of just fizzled out yet again. I did not know then of her addiction issue and did not find out until six to seven months after when she apologetically came to me confessing it and that it was a problem she has and didn't want me to think less of her or to think she didn't care about me.

So, it was about two years later that Kate and I hit things good and rolling. We were dating and things got serious. As of course my curse I have a kind of size issue so with that bit of concern I felt that things with Kate were in a place that because of how long we had known one another and how great of a connection we had that I could open up and speak candidly with her without worry. The talk happened to which Kate seemed to be unphased by the size issue and queried as to why I felt it would be an issue. This now led to opening up about Jessica and college. While hearing all this I could see that Kate was not only intrigued by it all she seemed to rather enjoy the aspects of it all. She began asking more pointed questions as to if I still had an interest in all that and if I felt that it was a part of who I am or if I had enjoyed it all. I am sure it is quite obvious where this was heading. Kate with somewhat excitement as to hearing my answers asked if this was something I wanted for us. To which my answer was I am not sure cause it had been years and not sure. I could see the excitement dwindle in her with that response. So, knowing that it was something I had previously enjoyed and how much I adored Kate I said sure let’s do this.

To which Kate jumped up with excitement, stopped, and said, "Wait though. If this will not make you happy and this is not something you will enjoy, I don't want to do this. I want to make you happy and hearing you talk about it I could see you get aroused and I could see that it was something you like."

At this point, I could not deny her observations as yes, I very much had gotten aroused during the discussion. It was very much a certainty. So, I completely fell back into the world of being a cuckold again.

Kate followed up by saying, “Yay I am so excited to do this!”

Kate had a guy that was a previous friend with benefits and that she felt comfortable with so she used him at first. His name was Brian and he was tall, thin, and of course well endowed.  Kate would go on to explain that Brian was amazing in bed but was more of a man child with no ambition. That was why she never felt anything more for him.

The first time that she and Brian hooked up after we had become officially a couple I felt as though I had instantly been transported back to college and the first night that Jessica was with another guy. I was unsure of why all the insecure feelings had come back. I was confused with my emotions. I remember thinking I have been through this before why am I worried?

My phone began to sound off with notifications. One after another after another. I sat up thinking what in the world is going on. I looked at my phone and saw photo after photo and then the video. The photos had begun with just some playful stripping and nude photos of Kate and also of Brian. Wow, I thought as I saw the final picture before the video. For such a tall thin white guy he had a huge cock. I sat with my jaw agape thinking oh my God that thing has to be like nine-plus inches soft. He is going to wreck her. Then I opened the video.

The video began with Kate laughing and saying, “Oh babe, I have so been needing this. You just don’t know what it is like having a boyfriend with a baby dick. I mean a girl needs real dick.”

The video continued and I heard Brian laugh and say, “Wow, like he is that small and you are still dating him while you are here letting me fuck you?”

Kate replied, “Yes, because even though he does have an itty bitty dicky, he is the very best boyfriend a girl could ask for.”

I could hear Brian’s uncontrollable laughter saying, “Itty bitty dicky! Hahahaha! That’s the funniest thing I ever heard in my life.”

The video was amazing all the way through. Kate played it all up amazingly and after all the initial joking things got serious quickly. She went straight to throating his huge cock as if her life depended on it. I mean I haven’t seen cock sucking like that unless it was in porn. Then the sex was so erotic and primal. It was bareback and hardcore and the amount of cum that oozed out of her pussy after he pulled out shocked me. In all the times with Jessica that I licked up behind her lovers, I never saw the amount of cum that I saw in Kate in this video. I instantly got a raging hard-on and wished I could have been there to lick up behind Brian. 

Things with Brian never progressed to my being there because Kate didn't think he would take to it and might be put off by some of all she knew I had done previously. Brian began to catch feelings to which Kate swiftly terminated any interactions with him. Which took us to a slowdown point in the cuckolding. Kate was rather new to it all so it was rather cute and funny to hear her try and be dominant and to say things to be mean or humiliate my size as it was not something she had done before but she did pick it up and get better as if it came naturally to her over time. Kate came home one day and told me how this black guy named Deontae was hitting on her at work and that he had given her his number.

I asked Kate, “Well did you call or text him?

Kate replied, “No, I didn’t babe. I have never been with a black guy before. I am not sure. I uh, I don’t know hun.”

I had told Kate to go for it. It's totally hot. Kate after having seen the guy at work a few more times and after some more interactions with him finally took the step. So, again as with the first night with Brian my phone blew up with notifications from Kate. Photos and photos and videos. Kate was not one to stray from what had worked before and had a very similar back and forth she had to begin with Brian with the one difference that She told Deontae about my being a cuck and my knowing she was going to be fucking him. Surprisingly Deontae was not quite as long as Brian but was much thicker. As each thrust from Deontae into Kate, I could see her pussy being stretched and stretched. Her moans with Deontae were louder and more passionate than with Brian. Deontae was a master at his craft of fucking women for sure.

I eagerly awaited Kate’s arrival as her next text had been that she was on her way over. As soon as Kate entered through the threshold she jumped at me, giving me a huge kiss and a big hug. Kate was glowing. I could tell she thoroughly enjoyed herself with Deontae.

Kate released her embrace and said, “Oh my God, he so filled me up, baby. I want you to eat my pussy and taste him right now.”

I knelt before Kate at which time her shorts fell to the floor and I began to pull her thongs off. As I pulled them down, I could see Deontae’s cum leaking from her full pussy lips. I couldn’t help myself. I buried my face and began to lick her pussy and his cum out of it as if it was my last meal. I almost came immediately from eating her pussy and tasting Deontae. It was amazing and we had the most passionate night of sex I have ever experienced.

It was two nights later when Kate calls me and tells me she needs a ride home. I arrive to pick Kate up and she went on to explain how she didn’t need a ride but that she had something else in mind.

Kate looked at me and said, “Babe, we are going over to Deontae’s. I want you to meet him and hopefully, we can all have some fun today.”

I looked at Kate and said, “If that is what you want then you got it.”

We pulled up to Deontae’s apartment and as we walked up to the door, I could feel my heart pounding and racing like never before. I stretched my arm out and knocked. Deontae opened the door and there he stood towering over me and letting out a scoffing laugh.

Deontae looked right passed me to Kate and said, “Haha wow so this is your little dick boyfriend huh. Well, come on in you too.”

Kate stepped in first leading me in as she already knew the layout. Kate looked back at me with an evil grin and smirk like there was a lot more she knew about what was about to happen than I did. Deontae and Kate led the way back to the bedroom and to my surprise there stood Javon. If Deontae seemed to be a large man in stature Javon was his equal or slightly bigger. It was at this point I knew that things certainly escalated in the talks between Kate and Deontae. Javon looked at me as though sizing me up and laughing looked at Deontae questioning if I was the guy. Deontae looked at Javon and with a smirk and bit of a devilish laugh nodded.

Kate turned, looked at me, and said, “Baby, take a seat right there and relax. Javon is Deontae’s best friend and when he was talking about me to him Javon said he just had to get in on this. So, I hope you are ready to watch me take both these guys but first you will have to suck them hard for me.”

The look on my face I am sure was enough to give Kate the obvious perception that, that little revelation was certainly not one I was ready for. Had I been down this road before? Yes, but it was not something I would have said this is what I wanted.

Kate noticing all of that then said, “Babe, is it ok? I mean I just thought from the stories you told me in the past that you would love this.”

I replied, “It’s ok it is just not something I guess I was ready for but it’s all good, let’s go.”

As I proceeded to get down on my knees, BAM Deontae slapped the right side of my face with his fat cock. I was startled, to say the least, and looked up at Deontae and then over to Javon who had just dropped his jeans and boxers revealing a monster of a cock.

Deontae looked down at me after slapping his cock across my face and said, “I hope you are ready you little sissy faggot. Now open that pussy boy mouth of yours and get to sucking.”

Every ounce of masculinity fled my body in that instant. What little control I thought I had over myself had disappeared. I wrapped my mouth around his cock so fast it was like a starving whore getting her first chance at cock in months.

Deontae looked back at Kate and said, “Damn your bitch can suck a cock girl.”

Kate spoke up and said, “Hey that’s good enough it’s my turn baby. Javon, your turn stuff your cock down my sissy boyfriend’s mouth.”

Javon walked over and as Deontae had, Javon slapped the left side of my face with his monster cock and without hesitation just shoved it in my waiting hungry mouth. As I sucked and sucked away at Javon’s cock, I could see Deontae just pounding and pounding away at Kate’s pussy as her screams and moans of pleasure were probably heard across the apartment complex.

Kate sat up and said, “Javon come on over here I want you both now. Leave my little sissy faggot of a boyfriend alone to watch you guys fuck me into a coma.”

Kate had made leaps and bounds of progress being a dominant cuckoldress. I raised off my knees and sat back down in the seat with my barely three-inch hard dick in my hand about to start jacking off to seeing my girlfriend getting her pussy pummeled by two Big Black Cocks.

Kate looked over towards me with a smirk and a wink and said, “That’s it baby jack that little dick off cause, I am getting real cock right now.”

Just then I heard Deontae let out a gruff groan and could tell he just unleashed one hell of a load of cum inside Kate’s pussy. He quickly reached over to Javon who was being jacked off and sucked by Kate and pulled him over so he could plug her eagerly awaiting pussy for another cock.

Kate let out an almost inaudible moan and awe of surprise when Javon slammed his cock inside her as if she wasn’t ready for how big of a monster cock he had. Javon fucked her mercilessly like he was taking out his world of anger on her pussy. Deontae walked back over to where I was sitting with my little dick in my hand stroking and shoved his cock back in my mouth.

Deontae said, “Here suck your girls pussy juice off my dick, bitch. You suck cock good too. I may just turn you out as my cock sucking bitch.”

As I finished sucking Deontae’s cock clan he pulled out and walked away to the bathroom. Then I heard Kate orgasm for what had to have been the fourth time. Then Javon I could tell was busting his load. Before he could finish, I could see Kate motioning for me to come over to eat her pussy and get ready to clean up. But before I could, Javon pulled out and then shoved his cock in my mouth obviously for me to clean him up first. Kate arched her back up in hopes of keeping as much of that cum in her before letting any of it ooze out to where I was not able to lick it up.

Javon pulled his cock out of my mouth, slapped me on the ass, and said, “Good game bitch.”

As Javon walked off, I dove into Kate’s pussy to eat her pussy and lick her clean of all the cum that Javon and Deontae dumped inside of her. I ate Kate’s pussy for what felt like forever when Deontae entered back into the bedroom.

Deontae said, “Hey bitch boy. Take your girl home and be ready for more cock sucking coming soon you little dick faggot.”

Kate followed up behind him and said, “Baby I think it’s time to go.”

Kate and I got dressed and left to go back to my place. We had what I thought was amazing sex that night after all of that with Deontae and Javon. Unfortunately, it was not long after that, that things with Kate went south again. I don't believe it had anything to do with the guy or guys but more, so I had been failing to notice Kate was struggling a bit more with her addiction issues but was masking it all very well. Kate had gotten herself into some trouble and we never really enjoyed things with any new guys after her Deontae and Javon. She was now going into a clinic and having to get clean.

I felt as though I failed her by not picking up on the signs or little cues. She had told me she conquered it all. I foolishly believed it and blindly went along with it. After Kate completed the program and was released we kind of lost that spark we had. Kate and I are not communicating much as she has a full desire to focus on getting herself into a better place and be a better person the kind of person she once was and wants no distractions. I cannot fault her for her desire and wish to be the better side of herself. I still miss her and wish we could be together, but her happiness means more. However, through this second experience, I had finally accepted the fact of being a cuckold and of my cuckold life. To the extent I had asked and communicated with two girls, I dated short term and asked some questions and about some of this, and to which they both said yeah, they knew there was something about me they saw but of course at that time didn't know anything about cuckoldry and now afterward a lot of things made sense.

Will Kate and I ever rekindle and reconnect on that level again is a question I do know the answer to or if it will ever be a possibility for her. I do know this though. I have accepted and come to terms with who and what I am. Who knows what the future holds or if I will find that one true love? But I am not as worried about trying to find love anymore these days. I just will let life happen and let those come into it that want to be in it.