1. Introduction and Apologies
Hey everyone, hello again. I know my last post probably had a ton of mistakes because I’m not a native speaker—and after re-reading it, I realize I might have messed some things up. What I meant to say is that now I’m definitely a cuckold. I’ve got no excuses, but I really want to share stories from my life with you all. I've now used the help of AI to help me express what I wanted to convey more accurately. I’m going to write another one now, and if you’re interested, I can keep writing more. I don't have any old photos left but if we get to my last relationship I have a lot to share. Let me know in the comments if you want to read it.
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2. Memories of My First Girlfriend
Last time I told you how everything began and ended with my first girlfriend. After we broke up, I was depressed and spent a lot of time thinking about my life—wondering if this was all I was meant for, with my body and my tiny dick. I started to pay more attention to porn about affairs and cuckolding.
3. Meeting Anna: The Start of a New Relationship
One day at a party, I met a girl. She was very striking, cheerful, and flirty. I don’t know what she saw in me. She was about 5’5?, had a slim waist, and a size three bust. Her big eyes and long red hair were simply stunning. That day, our group was drinking, and afterward I decided to step away for a bit to be alone—since when I got drunk I often felt sad about my ex. After a while, she came over to check if I was okay. Since I was already drunk, I told her I was missing my ex and briefly mentioned how she’d cheated on me more than once without going into too many details. She comforted me; we chatted a bit and then rejoined the group.
They say redheads are like fire—and that was definitely the case. The next day, she invited me out, and I agreed. We had a nice, casual conversation about all sorts of things, and then she wanted to know even more about my past relationships. I got a little embarrassed and blushed; in my head, I thought, “What am I doing? I’m telling a barely acquainted person about how I was a cuckold for my ex.” But I went on, explaining in somewhat more depth—without too many details—that the main reason was my tiny dick. The situation turned me on, though I suspect she noticed—and she just smiled playfully.
After just a few more of these encounters, she kissed me. I was surprised and dazed—I wasn’t sure why this was happening at first. She was incredibly hot and passionate. Then she invited me to her place, which was closer than mine. She lived alone in an old house. Once we got there, we had a glass of wine and she immediately grabbed my lips again. She was on fire and very persistent. I was wildly aroused and realized she wanted more. She noticed I had a hard-on in my pants, reached out to touch it, and said that it was really small—something she’d never experienced before. I was completely confused and embarrassed. We downed another couple of glasses, and it ended with a wild session of sex—or at least that’s how it felt to me, though she clearly got more pleasure out of giving oral.
I’m telling you all this so you know what kind of situations I’ve gotten myself into. We had a lot of discussions about why it all happened, and the most important thing was that she’d always secretly wanted a bisexual cuckold situation, though she hadn’t fully understood it before. She made me lick her cum off her body so many times. And I, having already accepted myself as such, agreed to this kind of arrangement. A couple of months later, we even found a bi guy—a guy she had known from before and had slept with often. She knew him well, knew what he liked, and she prepped him for meeting me without revealing the full surprise.
4. The Arrival of Alex: A Turning Point
The big day arrived: my girlfriend and I were at her place, drinking. That evening she wore a short black dress and a beautiful lingerie set. I was nervously joking and rubbing my sweaty palms all night. She was much more confident and cheerful, reassuring me that I was ready and that I would be able to handle it. She kept talking about how her friend had a big dick that could satisfy her better than any of our toys—pushing me to be braver.
Suddenly, the doorbell rang and Anna (my girlfriend) ran to answer it. At that moment, my heart started pounding like crazy—I went pale and froze. I heard her greet someone, and then his voice came. His voice was heavy and rough, which scared me a bit since I’d only heard about him and never seen him. I was in the kitchen pouring a third glass when my happy girlfriend returned, holding his hand. He was Alex—and he was even taller than me (about 6’7?). He extended his hand for me to shake, and I couldn’t help but notice that his two fingers would already be bigger than my thin dick. I gulped and handed him a glass in return.
For the next two hours, we sat and chatted about all sorts of topics, downing several bottles of wine. The more we drank, the more I noticed Anna getting increasingly aroused—her actions growing bolder. She’d lay her head on his shoulder, stroke his arm or leg. I also noticed that Alex kept looking up and down at my girlfriend’s cleavage, and his eyes told me he wanted her like before. My jealousy welled up, but my cock was already rock hard. I was nervously fidgeting and gulping wine.
Then everything changed when Anna asked Alex if he remembered how they used to have fun together. I choked on my drink, and even Alex was taken aback, asking if it was really appropriate to bring that up in front of me. But Anna was insistent—it was like she already knew exactly what she wanted to do. She started saying how much she loved it when he took her roughly, and that maybe he could do it again tonight. By then I was coughing, blushing, upset—and yet aroused. Here I was, watching my girlfriend cuddling with another guy, and it turned me on immensely. I was red as a tomato, and my dick was straining. Alex looked surprised too, but his eyes lit up. I think they both noticed my hard-on. Alex asked if everything was okay and what it even meant, to which my girlfriend replied that it was our first time trying something like this and we’d like to try a threesome. All I could do was nod in disbelief—my mind was reeling, sometimes I could barely even think.
5. Intense Sexual Encounters
For a while, everything felt like it was happening in a haze. Then I saw Anna drop to her knees in front of Alex and start kissing him, caressing his neck and chest—she looked so tiny compared to him. It was incredibly arousing. His large hand was squeezing her ass so hard I even wondered if it hurt her a bit. I continued sipping my wine, feeling completely helpless, as if cornered. Then she got up on her knees between him and urged me to come closer—but I couldn’t bring myself to stand. Suddenly, she shouted for me to come closer. I’d never heard such determination and a threatening tone from her before; it spurred me on, so I obediently moved over. Alex smirked and seemed to understand everything. When I sat next to him on the couch, he patted my shoulder and told me not to worry—that they’d done this plenty of times and I’d definitely enjoy watching. My girlfriend gave me a sweet smile and even congratulated me for “complying.” I felt so hurt and humiliated, yet I couldn’t stop watching what she was about to do.
Anna then pulled Alex’s jeans aside, revealing a huge bulge under his tight underwear. She began fondling it and commented that it was exactly the size she liked, and that my little one was just a “pencil in a glass.” They both laughed, and then she pulled his underwear off. Although his cock was a bit limp at first, it was still significantly bigger and thicker than mine. She grabbed it in her hand, exposed his big head, and then completely shoved it into her mouth. She cradled it as if she wanted it to grow in her. I noticed she was struggling a bit—her head tilting back further as he was too big to fit easily, forcing her to open her jaw wide. It was a very big cock—definitely more than 8 inches and very thick. Alex tossed his head back, closing his eyes. Anna was sucking him greedily and licking his balls, occasionally glancing at me. After she paused, she grabbed my hand and asked if what I had imagined in my fantasies was matching up to what I was seeing. I felt awkward but nodded obediently. Alex laughed and told me not to worry—that she was even more active than that and it was only just getting started. I hung my head, feeling both humiliated and burning inside. Anna noticed and kissed me on the lips; she was all slobbery and smelled of his cock. That made my heart race, and I was on the edge.
6. The Continuation in the Bedroom
She then led Alex into her bedroom and beckoned me to follow. Once in the room, she pulled my pants down to show Alex my tiny dick. He chuckled and told me not to stress—since at least he was there to help her cum several times. I hesitated for a long moment, feeling both upset and humiliated. Anna stripped down completely and lay naked on the bed, indicating a spot for me near her mirror. Alex also undressed and followed her. He eagerly began to lick my girlfriend’s pussy, remarking how damn wet and hot she was. It didn’t last long. In front of me unfolded a scene straight out of a porno: my girlfriend lay with her legs spread, and Alex was all over her with his big cock. He lay on top of her and plunged in roughly. Anna screamed louder than I’d ever heard before. I noticed that his cock wasn’t even completely inside her, yet she was already gripping his legs tightly and asking for it to go deeper. Then Alex fully inserted and started pounding her roughly. Anna screamed as loudly as she could. Alex’s balls swung low and smacked against my girlfriend’s ass. I got so aroused that I started touching myself until I came—so fast it surprised me.
Soon after, Alex flipped Anna over and positioned her face toward me on her knees. When she saw me all covered in cum, she laughed and motioned for me to come over and kneel at the foot of the bed. She took my hand and Alex started fucking her roughly. She clutched my hand so tightly that it sometimes hurt. Damn, it was so intense. It lasted about ten minutes until, after a few powerful thrusts, Alex came inside Anna!!! I panicked and fumbled, but Anna reassured me that everything was fine—she’d been on medication for a while, though she hadn’t told me. I felt hurt because it was something personal, but at the same time, I got aroused again.
Alex left for a shower while Anna lay on her back, telling me how that thick cock had torn her up and that she’d needed it for a long time. I sat by the bed, trying to process it all. Then my girlfriend asked me to strip completely and get on the bed. I obeyed; she turned her pussy toward me and said that if I wanted, I could lick her just like I did when I came inside her. I felt incredibly awkward, but silently leaned in. Her pussy was so stretched, so hot and wet—and Alex’s cum still oozed out of it. I closed my eyes, stuck out my tongue, and went for it. It was both horrible and insanely arousing at the same time—I licked like it was the last pussy I’d ever taste. Just then, Alex came in and smirked. It was awkward, but he calmly told me I was doing fine and that I should like it.
After her pussy was clean, and with me rock hard, I moved back and sat on the bed. Anna wanted to say something to Alex but then remembered that he was bi and had never actually been with a guy before—even though she really wanted to. I got scared; I looked at her, looked at his cock hanging, and didn’t know what to do. I felt a knot in my throat. Anna told me to sit still and suggested that Alex should play with his cock. Alex grinned and climbed back onto the bed. There he was—on his knees in front of me, his cock near me, and I was staring in fear. He put his hand on my head and told me not to be shy because it was really tasty and, besides, my cock was hard—so I must really want it. Anna edged closer to me, sat beside me, wrapped an arm around me, then took his cock with her other hand and directed that soft cock toward my face. I felt the pressure of her other hand, and before I knew it, his cock was right in front of my lips. “Don’t be scared,” Anna said, “open your mouth.” I closed my eyes, licked my own cock, and placed it in my mouth. “Good boy,” Anna cooed, “see? No big deal—deeper, deeper,” and pushed me further. I started feeling it filling my mouth and choked a bit. Alex and Anna laughed. “Come on, just do it—don’t be so timid,” Anna said, and I obeyed her command: “Good job, suck it; make sure to get it well-slicked with your spit.” I felt humiliated doing it—I just couldn’t believe it. I was overwhelmed with emotion. “Enough,” Anna finally said, and asked Alex to fuck her. She got on all fours and told him to lie down beneath her. I silently complied—Alex got on top of me. His balls were so huge that they almost touched my face. He nudged his cock toward my lips and told me to lubricate him once more before he re-entered Anna. It was like a scene straight out of a porno. He was fucking her and I was watching so close. Overwhelmed by my emotions, I started jerking off again. This went on for about 10–15 minutes until Alex came and immediately left. More of his hot cum started dripping on my face, and then Anna quickly straddled him. She grabbed my hair and told me to lick and not stop. She came again.
7. The End of the Night and Morning Events
They sent me to the shower to clean up. I looked in the mirror—my face was covered in cum and my girlfriend’s juices. I felt hurt, sad, happy—every emotion mixed up. I washed up, dried my face, and then heard my girlfriend yelling from the other room. Damn, they were already doing it without me! I wanted to get back to them as soon as possible, but the door was locked. I knocked and got told that now they wanted to enjoy themselves as a couple. That hurt, because my Anna was there, being fucked by her friend. I grabbed some wine bottles and sat by the door for a long time. I even came one more time before finally passing out.
In the morning, I was woken by the sound of the door opening—Alex and Anna were leaving. They saw me naked, with an empty wine bottle and dried cum all over, and they laughed. She kissed me and told me to get dressed, clean up, and join them for breakfast. When I returned, breakfast was already set for the three of us. They sat there happily chattering away. Anna was in nothing but her panties, and her bare breasts excited me. Alex was also just in his briefs, while I was fully dressed. We ate breakfast and I barely said a word.
Afterwards, Alex left, and Anna and I sat together, drinking and talking for a long time about what had happened and if everything was okay. She apologized for how quickly things had escalated, that she’d drunk too much and was totally overcome by passion for Alex—but she admitted her love for me. I shed a tear and confessed my love too, even though it hurt.