Locked Up Ch. 03: Maid Maria

"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.

"Well, ok it sounds like you MIGHT be good enough for her, but I'm still going to have to test you more closely. Don't you say a word when she comes back. If she asks, just say I went to the bathroom." Before I could respond, she looked furtively left and right, and then dropped under the table.

By the time Gwen returned, I was flushed, and struggling to control my breathing. Under the table Maria has pushed my legs apart, unzipped my fly, and fished out my rock-hard cock. One of her small hands was in my pants, cupping and fondling my swollen balls, and her lips were wrapped around the head of my cock, sucking hard.

"Where's Maria?" Gwen had asked me, looking around confused.

"She um... she went to the bathroom, I thought she would, would pass you on the way." Gwen had frowned at me, and I suppressed a gag. The lips around my cock slid lower and lower until Gwen's best friend swallowed my whole cock without a sound.

"Are you ok baby?" Gwen asked, looking concerned. I felt the warning squeeze on my balls, and just nodded.

"Fine baby, it's just the wine. You know I don't drink much."

The next few minutes were agony, as I tried to make small talk with Gwen, and ignore the expert blowjob I was receiving under the table. Maria was slowly increasing the pace, and I was having more and more trouble keeping calm. Finally, Gwen stood up, announcing she was going to check to make sure Maria had not fallen in or gotten lost. As she did, Maria's hand found the base of the plug stuffed into my sensitive ass. I groaned, hoping Gwen did not hear as she walked away. Maria increased the pace just a bit more, and I felt my orgasm overtake me, her hand twisting and tugging the plug in my ass, her lips sucking harder on my cock. I bit my tongue, turning my cry of pleasure pain into a muffled whimper as once again the ring did its wicked work, allowing not a drop of cum to escape my increasingly aching balls.

Before Gwen could return, Maria zipped me back into my pants and slid up from under the table, licking her lips, and then carefully touching up her smeared lipstick. "You did well. Maybe I will let Gwen keep you. Not a peep and I did not taste even a little bit of seed. Not all men take to the ring so well, you know." I just nodded, and as soon as Gwen returned to the table, looking even more confused at Maria's return, I excused myself to run to the bathroom. I overheard Gwen asking Maria how they had missed passing each other twice on the way but did not hear their response. Once safely in the stall, I carefully cleaned the evidence of Maria's lipstick off my cock, glad I had been wearing black pants, and black underwear. I readjusted my plug so it was not pressing quite so hard on that special spot, and then washed up, splashing cool water on my face and trying to calm down. I felt a bit ashamed at not telling Gwen about the blowjob I had just received from her best friend, but for all I knew this was part of the religious testing. The question was, did I pass if I did not tell her, or if I did?

The food came, and the rest of the meal passed in a blur. I tried to hold up my end of the conversation, but I was lost in debate, trying to decide if I should tell Gwen, or keep quiet as Maria had ordered. Eventually, the meal was over, and we headed for home. Once home, Gwen got Maria settled in the guest bedroom, and I grabbed a shower by myself for the first time in almost four months. Gwen was in the room as I stepped out, and just smiled, watching me dry off. When I was dry, I moved up to her, and opened my mouth, resolved to tell her what had happened. Before I could, she pressed her fingers to my lips, and followed them with one of the larger ball gags. I opened my mouth to protest and to tell her that I had something I had to tell her, but she just pressed the gag home, muffling me.

"Hush baby, we can talk later. I am SO horny after dinner tonight, but we can't have you making noise and waking Maria."

I was in no position to argue, and once the gag was strapped in place, there was nothing I could do. I followed Gwen into the bedroom, and helped harness her into her usual huge, red strap-on. That done, I assumed the position on the bed, in doggy style. Gwen climbed up behind me and pulled the restraints out from under the mattress. I held still as she cuffed my hands to the headboard, and pulled my legs apart, cuffing them to the sides of the bed, leaving me face down ass up, open and exposed. The restraints had become a regular part of our play, as had the blindfold she slipped on next. Trusting in the gag to muffle my voice, I let out a moan as I felt the lube caress my exposed hole, unplugged since my shower, and let myself relax as Gwen slipped her fat cock easily inside me. A month of constant anal sex had turned my formerly tight ass into a true boicunt, and Gwen wasted no time fucking me hard.

The gag muffled my moans and cries, but I still worried about Maria hearing us, at least until my first blocked orgasm hit. Past that, I was unable to do anything but take it, lost in the painful pleasure of my sensitive ass, and oh-so-full balls. Much sooner than I expected, however, Gwen pulled out, telling me to hold still, and that she had a surprise for me. I was just starting to recover when I felt more cool lube caress my open hole, and then felt Gwen's cock press against my ass.

At least I thought it was Gwen's cock, until she started to push, and I felt a much wider head pressing against my hole. Gwen had stuffed some bigger plugs in my hole before, but this felt more like a cock and it was much bigger than her usual strap-on. I whimpered as I felt myself forced to stretch more and more. I had not felt this tight since Gwen had popped my cherry, and I guess she could tell, as she spoke, one hand reaching around to stroke my cock. "Come on, Davey, relax for me. I know it's a little bigger, but you're going to love it, trust me."

I could only whimper, feeling as through I was going to split in two. Gwen continued to whisper encouragement to me as the painful pressure mounted. Just as I thought I could not take it anymore, I felt the massive head slide inside, and a warm pair of lips wrap around my cockhead. I groaned, shuddering in my restraints, whimpering against the gag, as I realized what was happening.

"Spoilsport." I heard Maria giggle, and heard a muffled response as Gwen tried to talk around the cock in her mouth. Bound and gagged, I could only take it, feeling what I was guessing was Maria's own strap-on stretching me wider and deeper as Gwen's talented lips on my cock distracted me from the too-intense sensations coming from my stuffed ass.

"How do you like my cock, Dave?" Maria asked, leaning forward across my back, pressing it even deeper inside me as she molded her breasts against my back. "It used to be your fiancé's favorite." I shuddered at that and started to orgasm as Maria hilted her fat cock inside me, filling my head with visions of my lovely tight fiancé stretching around what felt like a truly massive horsecock.

I lost count of how many times the two women forced me to orgasm that night, the pressure in my balls building and building until I was sure I was going to pop or go insane. Eventually the blindfold and gag were removed, and I was allowed to look over my shoulder and see Maria's huge cock. It was not, honestly, that much bigger than Gwen's. The position, the blindfold, and everything had conspired to focus my attention completely on my backdoor, but it was at least a couple inches longer and much fatter than Gwen's.

By morning, I was a stretched, aching mess, both of my holes gaping and sore. Yes, both my holes. Gwen got tired of sucking my cock and watching Maria fuck me, so she ordered me to give her a blowjob as well. This was new, and I flushed even deeper as my lovely fiancé and her hot maid of honor spit roasted me. It was difficult to swallow Gwen's fat dildo, but she was relentless, pressing it between my lips, and pushing it against the back of my throat, until it slipped down, my gag reflex triggering. Gwen would pull back a bit each time that happened, but only until I caught my breath before she pushed it down again.

By morning, I was a proper two-hole slut, Gwen's strap-on had been buried balls-deep in my throat, and Maria's was still stuffed up my boicunt. My balls ached fiercely, and I was positive they were almost as twice as big as they had been a month ago. I felt the pressure pushing against the unrelenting steel ring. Gwen and Maria had unstrapped themselves, leaving me stuffed, and were kissing on the bed next to me.

"So, what do you think? Does he pass?" I heard Gwen ask between kisses, with an unaccustomed trace of uncertainty in her voice.

Maria giggled before answering.

"He's a little tight, and a little small, but I think we can whip him into shape before the bachelorette party." The last thing I felt before passing out was the two girls' hands on my aching balls, and I could have sworn one of them said something like "it's a start".