This is the story of how my first girlfriend and I ended up in a long-distance relationship and what we ended up doing to make it all work. I’ve changed the names but everything else remains the same.
My name is Jason and I am a cuckold to my girlfriend, Stella.
She and I have been dating since we first met back in high school and at this point we’re both 18 years olds in college. Stella and I are students at different schools but since we are still very much in love with each other, we decided to have a long-distance arrangement. It wasn’t easy, which meant we had gotten very close to breaking up until we found the answer to all our problems by making this one change in our relationship. What does this all mean? How did this happen? I’ll explain…
I like it when my girlfriend has sex with other men. I like knowing about it, hearing about it, and most of all – I like seeing her in action when it happens. I like watching her with a tall, muscular, white guy – a guy with the kind of body I wish I had – and especially a guy with a thick, massive cock. I like seeing her with a masculine alpha stud that can fuck her how she needs to be fucked. When all is said and done, there is nothing I love more than watching a real man pleasure my beautiful, loving girlfriend in a way that my little dick never can.
Stella and I first met when we were both living in the city of B– and soon afterwards, we started dating. I felt extremely lucky to have her as my girlfriend because she was a gorgeous white French girl with flowing brown hair, a sexy petite body, perky round boobs, and an extraordinarily tight and smooth pussy. I didn’t notice it back then, but it’s obvious now that my fetish with being cuckolded started as early as when she and I began seeing each other. Stella was the first person I began having regular sex with and she was my first real girlfriend as well so it was her and her experience I looked up to since she was much more familiar with sex and relationships than I was.
My initial interest in her experience soon developed into an even stronger obsession about her romantic and sexual past – I was hooked. Stella always made sure to do whatever she could to make me happy, meaning we had lots and lots of sex and we experimented with all sorts of naughty activities. But, even with all crazy and kinky things considered, the one thing about her that caught me off guard, and which I could never forget – starting from the very first night Stella and I ever slept together, and during every time we did so after that, not only did she allow me to fuck her without wearing a condom, she also let me finish by cumming inside her pussy.
However, I found out that this was also the case for all the other guys she had ever been intimate with before… I learned by the time my girlfriend and I began dating, she had already fucked ten different men. By the time everything in the rest of this story happened, that number would rise up to a grand total of 14. Stella had bareback sex with every single she had slept and she had no issue with the fact that all of them had cum inside her.
I remember asking her how she felt about having unprotected sex with so many men. Stella told me she trusted all of them because she either knew the guy personally or that he was introduced through a mutual friend. Her main excuse was that she was on birth control so she even went so far as to say, “If he was already fucking me without a condom on, I just kind of expected him to cum inside me.” I didn’t see any of this as a bad thing at all. In fact, finding out how much bareback sex she had before me turned me on even more. Naturally, this led to me coming up with a nickname for my girlfriend, which accurately gave her the title of The Creampie Queen.
Shortly after Stella and I became a couple, I had really gotten to know a lot of the people that she was friends with quite well and that led to me becoming friends with them too. What I wasn’t expecting was how intensely this would further fuel my cuckold tendencies. Soon enough, I discovered that several of the guys I had recently befriended have had sex with Stella in the past. Knowing that so many of my new, and now only, friends have not only fucked my girlfriend, but have also creampied her was extremely arousing once I realized that all of them have been to places inside of her that only I should get to go now. This gradual discovery of how slutty my girlfriend truly was further provoked my curiosity and made me wonder just how far she was willing to go.
When I initially began asking Stella about all her sexual experiences and partners, she noticed I enjoyed hearing about it and that I wasn’t discouraged by everything and everyone she has been with so she began to open up more and more. She would describe what these guys looked like – lots of them were tall, white, handsome studs with very muscular bodies. Most importantly, they were all much bigger than me. I have the smallest penis that has ever been inside her, though she said it was still fun to be with. Even though I thought I’d be embarrassed about the size of my little dick, the thought of it being used against me turned me on. Knowing how many real men have pleasured my girlfriend with their huge cocks and cum inside her, it didn’t make sense that she would enjoy having sex with my tiny one. I wanted Stella to make fun of my small penis when we had sex and compare it to all the big dicks she had ever been with. It would have driven me wild just to hear her say, “I can barely feel your tiny uncut dick inside me. I want a real man’s cock to fill me up and give me the fucking I deserve. Your pathetic little dick doesn’t do anything for me. Is it even in yet?” as we made love to each other.
How turned on I was by small penis humiliation was nothing compared to my obsession with being cuckolded. The first obvious signs started when Stella moved away, making it so that we were in a long-distance relationship. Things seemed tough before she actually left, but appeared to ease up once we engaged ourselves in the long distance system; after more than a month together for summer vacation, we truly believed we connected enough to make it work. Things were going smoothly until my insecurities started acting up when she told me about this guy named Tim that began hitting on her. I was very jealous and worried after hearing about it especially since he was also asian but he was much taller and a lot more muscular than me – he even went so far as to say to her one night while their whole group was out on the town, “How about I be your asian boyfriend when Jason’s not here visiting you.” I soon became so scared of losing her to a manlier guy than me that I began to resort to the next solution possible – instead of fearing that Tim would steal my girlfriend away from me, I started becoming aroused at the thought of a bigger, stronger man making love to my girlfriend.
It was around this time that I began researching into the cuckold lifestyle, learning what I could and teaching myself more and more about it. I became increasingly turned on the more I learned, but I was still hesitant about letting Stella know because I was scared she would find it too weird seeing as how I voiced my concerns about Tim and the threat I felt from him. She comforted me and convinced me I had nothing to worry about, when it was clear she enjoyed his attention and obsession, but with how young and naive I was, I really couldn’t pick up on things. I soon became more and more obsessed with the thought of being cuckolded – my thoughts turned from “That guy is so much more manlier. I hope she’s not cheating on me with him” into “I wish my girlfriend would have sex with guys that are manlier than me.” I gradually began sharing these thoughts and my fondness for cuckolding to Stella. She was confused at first, and even thought it might be a trick considering how concerned I was that she might be having a thing with Tim, but after explaining things in detail to her and where I was coming from, and showing her just how turned on I was by the thought of it, she began to accept the fact that I was a cuckold.
I shared resources about cuckolding with Stella while I was still overseas and she was going to school in M–. She started to learn more and more about this fetish and began to understand where I was coming from – even including my small penis humiliation fetish after explaining to her how all of her sexual partners so far were bigger than me and how I could only assume Tim had a bigger dick than me too considering how muscular his figure was. Stella still had that drive within her that made her want to party because of her life in B– so she tried going out on the town as much as she could, which was much harder but she still ended up running into him more than a few times. Once her comfort with my fetish began growing, she started truthfully telling me how she was stirred up by his sculpted figure and alpha male attitude, and after seeing how comfortable I was hearing this from her, she became less shy and spoke up more about it.
My first time visiting Stella in M– was in October, during my birthday, which was more than two months after she moved there and more than one month of her being acquainted with Tim. Now that she was much more familiar with my passion of being cuckolded, she was willing to go further than she did before when we would talk about her being with other men or roleplaying situations. Also, it was such a turn on finding they were interacting with each other more than I thought they were. On the night both of us celebrated my birthday, Stella was well aware of how turned on I was at the thought of being cuckolded, she drove me wild with lust when we were making love because right as I was in the middle of thrusting in and out of her, she leaned closer to my ear and whispered, “I can’t feel a thing. You’re so small compared to him. Is that as deep as you can go?” And right as I was reaching the point of orgasm, Stella moaned so loudly and convincingly – almost like she had said it before – “OH TIM! DON’T STOP! Fuck me harder! You’re so much bigger than my boyfriend! Cum inside me, Tim!”
Once Stella saw just how much that dirty talk turned me on and how hard it made me cum, she became more open to doing that. When we would have sex, she’d always whisper right into my ear about how small I was and how much bigger Tim’s man sized cock was and how he could satisfy her when I couldn’t. However, at this point, I didn’t know if she actually slept with him or not. What turned me on even more was the thought of all the manly big-dicked guys I personally knew back in B– and how they actually had sex with the girl that I now looked at as my one true love and soul mate. It was the thought of them giving my girlfriend a creampie like the cum slut she is that turned me on the most. Once I voiced that turn on to her, she was very receptive to it, but thought we should start slowly and not delve into anything real just yet. I proposed the ideas of some dildos and other toys and she happily agreed to the idea.
Stella was scheduled to visit me in B– during her school’s winter break for a few weeks so I ordered a couple of toys to her address for her to bring back during her visit so we could use it together. There was lubrication, a ball gag, furry handcuffs, a male chastity device, a white seven inch standard girth dildo, and, most importantly, a very thick nine inch realistic black dildo that could attach to harness and act as a strap-on. She enjoyed the white dildo because it was about the same size as the guys she had sex with before she and I got together – a fact that turned me on immensely. However, I will never forget the time that I fucked her with the black dildo, that we named Marcus, for the first time. I blindfolded her so she wouldn’t be visually intimidated by the size, used copious amounts of warm lube, and (surprisingly even to me) got the entire nine thick inches inside her down to the hilt. She said she couldn’t even believe it, but I knew that she’s taken cock just as big if not a bit bigger.
The best part about fucking Stella with Marcus was how intensely she would orgasm when I penetrated in and out of her at the perfect speed and angle. She kept saying how size didn’t matter and that it was just a big dick but after witnessing the sheer amount of pleasure she was lost in, and how she told me the sensation of being completely filled up was overwhelming, and the feeling of having such a huge cock taken out of her was so gratifying, I knew she loved having a massive slab of man meat inside her no matter how much she denied it. The most pleasurable part for me was that it was the first time I was able to experience the pleasure of how it feels to be cuckolded. When I fucked Stella with Marcus, our nine inch strap on, her pussy was sopping wet and she was cumming nonstop over and over again. Right after I fucked my girlfriend with Marcus strapped on, her pussy was so stretched out that I couldn’t feel anything when little dick entered inside her . She even confirmed the same areas inside her that I would usually have to get to in order to make her cum had gone deeper inside her so that only Marcus could make her orgasm.
The best part about that first time was that I could tell how genuine Stella was when she told me she could barely even feel me after I fucked her with Marcus. She said I felt like a little finger poking around and that I should just give up because Marcus reached places so deep inside her that I will never be able to feel them no matter how hard I try – that made me cum right then and there. We had a lot of fun with Marcus especially when I would wear the strap-on harness with Marcus attached to it, warm up and lube up this nine inch monster, and make love to my girlfriend in the position that I normally would. The major difference was between her facial expression when we would have sex normally compared with the lust and wonder in her eyes when I thrusted in and out of her slutty pussy with Marcus’s nine thick inches after mounting her during sex in the same missionary position we always started with. I could tell by her enthusiasm that she craved bigger cocks and didn’t just say she did because it turned me on. I soon learned to love how wet and loose my girlfriend’s pussy felt when I fucked her without the strap-on while she told me how pathetic my tiny uncut dick was and how she couldn’t feel anything compared to all the real man sized cocks she’s fucked in her life. She told me that only big real man sized cocks could make her cum and that she was only fucking me and my little dick out of pity.
As much as Stella enjoyed having her pussy fucked by our nine inch Marcus, she still seemed to prefer our seven inch white dildo that was a little less wide and was the exact shape and size of some of her favorite sex partners before me. She was still visiting me in B– so we started talking about how much it turned me on thinking about her with some of the guys she has fucked before because I knew them and I knew they had sex with my girlfriend. After prodding her for a little more information, she told me she had a thing with this guy and that she fucked him quite a few times only less than a month before she and I started dating. I knew him fairly well and his name was Ryan. He was a tall, handsome white guy, which happened to be just her type, who was a few years older than us. He was also very good at keeping in shape which was shown by his very sculpted and very muscular body. Stella told me what happened between them – he took her home from the club on the night of her birthday party, which happened to be only three weeks before she and I started dating, and he had sex with her that night. He took her back to his place many nights after that and he filled her up with warm sticky cum every time.
That wasn’t even the best part. After Stella and I talked about her past sexual partners and their skills in bed as well as how attractive they still were to her, she confessed that Ryan was still very hot in her eyes and she really wanted to have sex with him again. She told me how he could last multiple sessions throughout the entire night, how sexy and sculpted his muscular body is, and how long and thick his large cock was. After hearing how enthusiastic she was to be reliving the experience, I was more than happy to oblige. Seeing as how I knew him fairly well and that they were good friends too, the thought of it drove me wild. I urged her to talk to him about it and see if there was something we could set up that break. I was so eager for my girlfriend to make me her cuckold and this just seemed like an amazing opportunity to do so. She ended up talking to him with me jumping in here and there to convince him that I was alright with the whole thing. He seemed pretty excited and we began to talk about ideas. Unfortunately, the timing didn’t pan out right and I returned with her to M– to spend a few months together.
Over the next several months while Stella and I lived together in M–, we gradually developed my cuckold fantasies together. Our roleplaying intensified and this would include Stella dressing up in different outfits, substituting my name for the names of her ex-lovers (especially Tim and Ryan) when we made love, locking me up in chastity and other bondage like gear, and her acting out fantasies of mine such as her getting fucked by a big black cock, being creampied by Tim, her seeing a guy this whole time and keeping it secret from me, etc. I would fuck her more often now with the strap-on while she pretended I was a different guy who was manlier and more muscular. I also had underwear made for us that made our positions clear if a bull were to ever see it – something that would come in handy before Stella visited me for the summer. Soon enough, she began talking with guys online. As we started approaching summer time, she finally found a man she was attracted to – his name was Rick, he had a very toned body, an alpha-male attitude, and he was a handsome and hung man just a little older than us.
At this time, I had to return to B–, but I still urged Stella to continue talking to Rick. She was scheduled to come to B– so we could spend more of the summer time together. Weeks passed and after innocent talking led to less innocent talking, she asked me if it was ok to meet up with Rick only 1 week before she traveled to B– to visit me. Of course I told her I supported her and I hoped that she would take some pictures and a give me a recap of what happened between them. I knew she would be more at ease without me there and that she would feel free to express herself more being that this was the first time she did this. She originally planned to have an innocent meet up with him where they only talked to have coffee, but after being away from me for so long, she was so horny by this point that she was desperate for some dick. Their first meet up was at a hotel where she ended up having sex with the eleventh person she’s ever slept with. She hadn’t met Rick in person before then – she had only talked to him for a couple weeks before that – and she still fucked him for many many hours on the very first day they met. The one thing that surprised me was how she let me have anal sex with her after dating for a year but she let him do that right after her first orgasm and after having known him for only an hour and seeing his thick, eight inch cock. Even better was the fact that Stella didn’t ask him to wear a condom once during the five rounds of sex they had all over their hotel room. Rick repeatedly fucked my girlfriend in the pussy, ass, and mouth and came inside her every single time. They did it on the hotel bed, couch, and shower. I was asleep and on the other side of the world when this was happening. As soon as I woke up, I texted her and the first thing she sent me was a selfie of the two of them naked in bed together followed up with many pictures, videos, and an outlined story of what exactly happened.
There is no way to describe how amazingly mind blowing the sensation I felt was like when I saw proof that I had officially been cuckolded. I masturbated so many times to those photos and videos and especially to the very detailed story Stella wrote for me of what happened. She was back in B– only a week later and we couldn’t stop having sex which was mostly me penetrating her in the missionary position as she told me how amazing it felt to be fucked by Rick and have his huge man cock inside her. She told me when they first began in the hotel room that she had to stop for a moment because it felt so strange to actually be with another man other than her boyfriend. He was very gentlemanly about it and offered to stop but, as proof of how much of a dirty slut she is, she continued on and fucked him until he came inside every part of her that he could enter.
After they were finished, Stella and I met up and something happened that I will never ever forget. She knew what my fantasies and turn ons were so she when finished, she made sure it was inside her. Once our bull was finished inseminating my gorgeous girlfriend, he went to clean himself up, leaving her alone with her little dick cuckold of a boyfriend. She started to role-play as soon as we were by ourselves – “Come here and fuck me. Did you like watching me fuck another man right in front of you?” As soon I was inside her, I experienced a pleasure that I’ve never felt before. It was the silkiest, most slippery warm sensation I have ever felt and I knew exactly why it felt that way, causing me to begin thrusting in and out of her sloppy, loose pussy immediately.
Stella could tell how much pleasure I was in and asked me, “I’ve been a naughty girlfriend tonight. Does it feel different being inside me this time? It’s because I fucked another man right before this and he came deep inside me. How does it feel knowing another man came inside your girlfriend just now and your little dick only get to fuck his sloppy seconds after he creampied me with his real man cock?” I came right then and there. We went back to my room after I came but it didn’t stop there. We continued to fuck a few more times and the best feeling I will never forget was how warm and slippery my girlfriends cum soaked pussy felt while I fucked her sloppy seconds. “You wanna know a secret baby? A real man came inside me tonight and your little dick is sliding in and out of that right now. How does it feel knowing you weren’t the first inside me tonight? Do you enjoy knowing your girlfriend is a naughty whore for huge cock? It’s not like you have a say since I can’t even feel anything right now with your little dick inside me after those big muscular men finished using my slutty pussy to dump their loads in.”
I was already a cuckold before this since she fucked Rick in M– before visiting me in B–. However, this was such a monumental occasion because it was the first time I got to make love to Stella’s sloppy seconds after another man came inside her pussy and left a creampie in there. The next step was when she traveled to F– to spend a few weeks there because of family. Coincidentally enough, there was also someone else who originated from that town – Ryan. Needless to say, she got in contact with him pretty soon seeing as how she’s been hungering for his cock and that she was already on a roll with cuckolding me. When she finally confessed to me how Ryan was one of the best fucks of her life and how she has been craving his big dick ever since, I eagerly encouraged my girlfriend to have sex with him as soon as she could. She met up with him two times that summer and they had a multiple hour long, overnight sex marathon both times. The way she explained it was the best. Even though she took pictures for me, the outline of their sex really helped one imagine things and will be added here. Obviously they didn’t use a condom seeing as how she’s still the Creampie Queen. Ryan told me himself that they even went to the pharmacy afterwards to get a morning after pill because he came multiple times and drained several huge warm loads of his potent alpha seed deep inside my girlfriends fertile, well fucked pussy. Making me feel like even more of a cuckold, they had sex on the bed, the couch, and the shower in the same apartment that Stella and I usually stay while in F–.
Ryan was also such a strong alpha-male man that he could fuck Stella just by lifting her up and down with her in midair – a fantasy of hers that she’s had ever since she opened up to me about what kind of men turn her on. The difference was that they actually spent the night together. That turned me on the most. And when she explained to me how they met, went to the movies, had sex as soon as they got home, and did it over and over again in all the details she provided, it didn’t seem like they were just having sex – it felt like they were making fiery passionate love. She told me how she had never cum so much in her life and that he was a sex machine. Stella went on and on about how their sweaty bareback sex was so raw that it felt like she was an animal in heat and that Ryan was savagely mating with her and breeding her like the beast he is. She was enamored by how his thick circumcised man cock that’s twice as long as mine hit pleasure spots so deep inside her that she had the most intense orgasms ever, especially when she could feel his 8-pack washboard abs touching her. It was then that I felt like the ultimate cuckold because my loving innocent girlfriend finally let her true colors show and allowed herself to be pounded and creampied by this muscular stud of man while begging for his throbbing manhood like the dirty little slut she is.
Once the summer holiday was over, Stella went back to M– to start school back up again while we continued our long distance relationship. Little did I know this was only the beginning…
to be continued…