"Ohh fuck, Gwen, yes, fuck my boicunt, stuff your fat cock up my ass!"
Words I never ever would have guessed I would say spilled out of my mouth before I buried my head in my pillow and cried out, my aching balls spasming as my fiancé fucked me to yet another massive anal orgasm. A month of straight anal play with no other stimulation had turned me into a total anal slut. I whimpered a bit, the pain warring with the pleasure as Gwen's strap -on continued to slide back and forth over my prostate, forcing my balls to struggle even harder to try and spill. Despite the constant pressure, however, her ring held me as tightly as ever. True to form, Gwen kept fucking me right through my orgasm, not letting up until I eventually collapsed on the bed, a sweaty, aching mess, my balls aching and swollen, my backdoor sore and stretched.
What had led me to this point is too complicated to go back over completely. Two months ago, three months into our engagement, my lovely fiancé, Gwen, had placed a tight metal ring around my balls that prevented me from spilling a drop of cum - a primary taboo of her crazy religion. This protected us from breaking the rules, but it was doing nothing for my frame of mind. I was half mad at this point and slipping further every day.
Not being able to spill was not quite the same as not being able to orgasm. It just meant that when I did try to get off, I could not empty a single drop of cum, and the pressure in my balls built and built. Two months in, I was positive my balls were actually getting bigger - much bigger - but Gwen kept telling me I was imagining things, and it was just the weight of the ring. I would have measured, but she had forbidden me to do anything so silly, and I had learned over the last two months not to break my sweet Gwen's orders. She was becoming stricter by the day, and I had promised to obey her for as long as the ring remained around my balls.
Not being able to pop my cork was wreaking havoc on my mental state. I have always been a horny guy, but in the last few months, sex has come to dominate my thoughts in a way I'd previously never imagined. For the last month it was anal sex, specifically. Not Gwen's ass, however, but my own. One month in, when I told Gwen how much not being able to cum was hurting, she told me she was going to start fucking my ass instead, as it was supposed to feel good for guys, but not make them cum. What I did not know at the time, but quickly learned, was that I am not most guys. Having her huge strap-on up my ass made me orgasm harder than ever and increased the pressure on my balls to an even greater extent. Gwen told me I was imagining things and, if anything, dedicated herself even harder to fucking my ass. Well, I should say, my boicunt, or boipussy. Gwen said a hole as eager as mine should have a special name.
The other thing I did not know at the time, was how dedicated Gwen was going to be to fucking my ass (boicunt) and only that. In the last month she had fucked me with her huge strap-on, with her fingers, and with other toys. Once, in the shower, she even fucked me with her tongue, which both shocked and turned me on in equal measure. After a whole month of this, my ass really was a boicunt, a well-stretched, horny little hole desperate to be filled. I wore buttplugs almost all the time now, even when Gwen did not order me to. Last week, I found out just how stretched out I had become. Gwen caught me trying to unlock my ring and shoved her whole fist up my ass as punishment. I could not believe my sweet Gwen was shoving her whole hand up my ass, or that I was coming over and over again from the painful stretching pleasure. I was sure my balls were going to explode before she finally relented. She made me promise not to touch the ring again, and I had been careful to follow that order. I did not know what she would do to punish me if she caught me again, but I was pretty sure my sanity could not take it.
It was after another of her marathon anal sessions that Gwen curled up behind me - her thick rubber cock still stuffed inside me - and asked if I was ready to meet her maid of honor. She told me that her childhood friend, Maria, whom I had never met, would be coming to stay with us for the last month of our engagement.
"The whole month?" I murmured, surprised, but too exhausted to raise much of a fuss.
"Of course, baby," Gwen had replied, reaching across my body to stroke my cock, sending a shudder through me. It was the first time in over a month she had touched it other than by accident. Just that sudden contact pushed me towards another orgasm, and I struggled to hold it off. The last thing I wanted was more pressure. "It's tradition for the maid of honor to view the couple in the last month of their engagement, to ensure they are a good fit, and that they are observing the scriptures." She gave my balls a tug as she said it, and I swore I could feel all the backed up cum sloshing inside my aching sack. "Of course, this ring is doing a great job of that, but we still have to follow the tradition."
The next afternoon, after bending over for Gwen in the shower, and receiving a thick plug that was to be my constant companion that day, I got dressed, and Gwen and I drove to the airport to pick up Maria. Almost the instant that Gwen and I met her in the concourse, I realized I was in for more trouble.
Maria was a knockout. She was shorter than Gwen, almost pixyish, with spiky blond hair and small breasts that pressed out noticeably against the tight shirt she wore. She jumped up to give Gwen a hug and I goggled as she gave my fiancé a more than sisterly kiss on the lips. When they finally disengaged, Maria turned to me, and I got the same treatment. She jumped up, wrapping her legs around my waist, and I struggled to catch her, feeling her weight press against my near constant hard-on. I would have sworn she wiggled against me as she leaned in to give me a big kiss as well, her tongue sliding into my mouth and back out again, so fast I almost did not believe it happened. I was still shocked when she disengaged and turned back to Gwen as if nothing had happened.
"So, this is the lucky guy, huh? I'm surprised at you, Gwen, I would have expected you to go with someone... bigger." Maria put just enough emphases on that last word that I flushed, almost missing Gwen's response.
"There are more to guys than just size you know, Maria." I blushed deeper, having expected Gwen to defend me in some way. Before I could muster a defense of my own, Maria turned Gwen and I around, linked her arms between ours, and practically dragged us out of the concourse.
"Come on slow pokes, I have been on that plane for way too long and I'm starving. Take me home so I can grab a shower, and then dinner is on me." We followed; it was impossible not to. For such a little thing, she was bursting with energy, and I had a feeling she would be dragging Gwen and I around for the next month. I had no idea. Gwen and Maria chatted on the way home, and I sat in the back and tried to think calm thoughts. Just being in the presence of two such lovely ladies had my cock pressing firmly against my slacks, and I struggled to find a way to hold my hands and legs to best hide it.
Once home, the girls disappeared into our bedroom and Gwen ordered me to wait on the couch. I heard lots of giggling, and then the shower turned on. I could have sworn I heard some low moans over the sound of the water but tried to tell myself I was hearing things. I turned on the TV to distract myself, but I could not even tell you what sport was being played, let alone who was playing, or what the score was. An eternity later the two ladies returned from the bedroom. Gwen was stunning in a tight red dress that hugged her curves and left little to the imagination. Maria was in a little black dress so tight that it was clear she was wearing neither bra nor panties.
I did my best to keep my tongue in my mouth and my cock from tearing out the seam of my pants as I stood and held the door for them.
"Wow, you look stunning tonight, ladies" I managed to say with more aplomb then I thought I could muster. Maria smiled, she had a great smile, and Gwen giggled.
"See, I told you he had some good qualities. Size is not everything." I flushed again, the compliment turning into yet another size crack. I meekly followed the ladies out to the car, and once again sat in the back as the ladies continued to catch up with each other. Maria directed us to one of the most expensive restaurants in town and led us right to the head of the line, her reservation getting us a table to ourselves near the back of the smaller secondary dining rooms.
Once we were seated, we made some small talk, and Maria ordered a couple very expensive bottles of wine. She poured each of us a large glass telling us to enjoy ourselves and that the evening was her engagement present for the two of us. I am not much of a wine drinker, but I tried some, and then more, trying to calm my nerves. This was the lady I had to impress in order to marry Gwen, and despite all the... pressure... I was under, that was still something I very much wanted to do. Maria asked me a few questions about my college career and my job, and I was doing my best to answer when I felt Gwen's stocking-clad foot brush my own and proceed to slide up my leg. I struggled to keep a straight face and answer Maria's questions as Gwen's foot slid higher and higher. I can't say I remember a thing I said, but I thought I was doing well, even when Gwen slid her foot between my legs, and started to stroke my very erect cock outside my pants, stroking back and forth.
At least I thought I was doing well, until Gwen excused herself to use the ladies' room, and the foot remained firmly on my crotch.
"Finally, some alone time," Maria grinned at me, grinding her foot even harder against my cock. "You're a little small for my best friend in the world, how do I know you'll be good enough for her?" I shuddered, closing my eyes, not quite understanding what was going on.
"I love her to death," I groaned out, trying to ignore the now almost painful pressure against my swollen cock. "She's smart, she's funny, we share a lot of the same interests, and I'll do anything for her. I even took a purity ring for her," I finally babbled out. Maria just smiled, finally pulling her foot off my aching cock.
