Testing the Limits

In my junior year of college, I became a cuckold. This is how it began.

In order to understand the situation, some background knowledge is needed. Me and my girlfriend Haley were both juniors in college, and had been dating for about two years. Haley was a beautiful girl, about 5 foot 2, with brown hair, and a curvy body with a little chubbiness in the right places. The factor about her body that had attracted me however, I am not ashamed to admit, was her ass. She had a massive, heart-shaped ass and thick thighs that simply enveloped me when we would have sex. I would often fantasize about her smothering me with those legs and forcing me to endure as much as I could take. I would stare at her ass as I followed her up the stairs, and I knew others were looking too.

I myself was far from ugly, a solid 6 foot flat, and our friends agreed we made a good match. Indeed, we had had a lovely relationship since getting together first semester freshman year, and I had the good fortune of being the first, and at the time only, man she had ever slept with. She had given blowjobs and handjobs before, but upon our first time having sex, she exclaimed I had the largest dick she had seen. This certainly felt good to hear, considering I was likely only a little over average in terms of length, and likely below average in girth. I was an attentive sexual partner however, and always did my best to make sure the both of us came, whether with my hands, dick, or otherwise.

So, for the most part, our sex life was good, and our relationship a healthy and trusting one. She and I were both part of greek life, with our sorority and fraternities mixing often, which worked for us nicely. When our houses would mix with other houses, we trusted one another to handle ourselves and remain faithful. For that reason, I'm unsure of why I began to develop a cucking kink my junior year. It began probably from watching too much porn, watching girls who looked a lot like Haley getting torn up by large, often black, cocks. It was always a guilty pleasure, watching these girls pussies cream on the thick shafts of these men, and even the most hardened pornstars' own bodies betraying them to lust.

I never shared this unexpected sexual development openly with Haley, but every time we would have sex, I began to think about how different it was from the girls creaming on these men's cocks and drooling into their sheets. I could satisfy Haley with my cock, but I could bottom out inside of her and it always felt like her pussy was hungry for more. Eventually, I bought her a set of dildos, ranging in size, for the legitimate purpose of helping her get off after I had already came. There was an ulterior motive to this purchase, as you may have guessed; I wanted to see how much her pussy could take, and wanted to see how she reacted.

One night, after a party where both of us had a little too much to drink, we pulled out the dildos. We had tried the smaller ones, up to one that was essentially the same size as my dick, but we still had 2 more sizes to go. After going down on her messily (I was drunk, everything was messy, alright?), I pulled out the second-largest dildo.

She eyed the dildo apprehensively at first, but the liquid courage got the better of her and I saw her eyes glaze over with want. She nodded almost imperceptibly, and I began to rub the tip of the dildo against her labia, wetting it at the opening of her pussy. The dildo was likely about 8 inches in length, and a great deal thicker than my own penis. I began to slide it into her, and she and I both shivered with nervous excitement. Inch by inch, her pussy accepted the shaft, slowly at first, but with more ease as she relaxed. She groaned, and I began to slowly work the dildo in and out of her, pushing in until it had bottomed out balls deep, and slowly retracted it until only the tip remained inside of her. She urged me on, lightly placing her hand over my own and encouraging me to pump her pussy with it faster. She took my dick in her hand and began stroking it while I pumped the dildo into her. I was extremely turned on by this point as you can imagine, and was fully ready to blow my load at a moment's notice. However, Haley had different plans.

She released my dick and pulled me down to kiss me, and then looked me in the eyes in the special, unfocused way only a drunk person can.

"I want the big one..." she whispered to me, my hand still pumping the dildo in and out of her as she said it.

I could hardly say no, and far from it: I had been hoping this moment might come. I handed the dildo off to her to let her keep playing with herself while I got the biggest dildo ready. This one was a behemoth; 10 inches in length and at least 2.5 inches wide, even I wondered if she'd be able to fit it at all or if she would just call it off. As soon as she laid eyes on it, however, I knew she would be taking it all. A hazy half-smile came to her face as she looked it up and down, and she silently spread her legs wide, removing the other dildo and tossing it aside. Her pussy was already warmed up, but I applied a little lube, considering the size of the tool. She began stroking my rock-hard dick again, but her eyes never left the dildo. I went much slower this time, wetting the tip and ever so slowly working the shaft into her pussy. She grimaced slightly as she adjusted, but a mix of the alcohol and her lust clearly numbed any pain she was experiencing almost immediately. She kissed me hard, and as we kissed, I worked the shaft in and out of her pussy, a little more each time. She started letting out low moans, from the back of her throat, every time the huge dildo came close to bottoming out in her.

I broke our kiss and gazed down. I almost couldn't believe it! Her pussy was distended, stretched wide, with her lips gripping the shaft of the synthetic meat tightly. The dildo was bottomed out in her pussy, a whole 9 or 10 inches deep. I'll never forget that sight, or what happened next. Haley had clearly become impatient with my slow and methodical easing of the dildo into her pussy, and she moved my hand out of the way less than gently, placing her own hand on the base of the dildo. With my dick in her other hand, she began working the dildo in and out of her pussy, hard. Her eyes closed to slits, and she turned her head away from me. I watched in amazement as her pussy got wetter than I had ever seen it, a creamy substance clinging to the shaft of the cock as it bored into her once-tight vagina. I could sense she was approaching an orgasm, her moans becoming rhythmic and guttural, and she let go of my cock so she could exert more force downward onto the dildo into her pussy. She was positively slamming it into her, and as her orgasm finally came, she squeezed her thighs together around the dildo and turned on her side, convulsing slightly and releasing low grunts into a pillow.

Eventually, she rolled onto her back, smiling at me in a deep, drunken satisfaction. She removed the huge cock from her stretched-out pussy, and tossed it aside. She looked at my cock: still rock hard, obviously. Lazily, she spread her legs invitingly. I stared down at her gaping pussy. Lube, sweat, and that incredible cream the cock had brought out of her covered her pussy; it was a mess. Slowly, I lowered myself into her, bottoming out on the first stroke. Her pussy felt wet, sloppy, and different than I had ever felt it. It was loose but so soft from the beating it had taken, and so hot, it felt like my cock was melting inside her. I began to thrust and she looked me in the eye as I did it. She didn't say anything that night, but I knew: she couldn't feel a thing I was doing to her.

This realization was too much for me. I lasted perhaps 10 strokes if i'm being generous, and then the pressure that had been building up became too much. I kissed her hard, and stuck myself in balls deep into her soaking, beat-up pussy, and released the biggest load I had ever shot deep into her pussy. She moaned lightly, and wrapped her legs around me as I came.

"Good boy... good boy...." she repeated over and over into my ear as I pumped load after load out of my balls deep into her womb.

Eventually, I rolled off of her, and we both fell asleep in each other's arms. Little did either of us know, that this wasn't the end of our sexual explorations, but only the beginning.