Cindy's Biini - That First Guy

With videos in hand that lay out almost every sexually deviant act I had engaged in, Shawn kept up his end of the deal and arranged for me to take care of my third pregnancy. This, of course, was to make way for my fourth impregnation from a pool of men that Shawn and the boys would choose themselves.

The clinic required a plane ride and an overnight stay, but afterward, I was once again without child, at least for a bit. They allowed me a recovery time, but soon, it was time to begin attempting to inseminate me again. At this point, I couldn't back down. With the tapes they had of me now, I was basically powerless against them. The deal was these eight men they picked would all get chances to impregnate me until, finally, one of them got me knocked up. It wouldn't matter who got the job done as they wouldn't be allowed to claim any of this happened. However, unlike my last several pregnancies, I would be required to keep this one and give birth. I was free to trick another man I slept with into thinking they were the father. I would just have to hope they wouldn't ever ask for a paternity test.

Shawn informed me that the first potential man to impregnate me would be at his house today, and I should come over ready to fuck. As usual, he promised everyone would be 18 or older. When I arrived, I wasn't surprised to find Shawn's friends Grant, Richie, Don and Teddy there. I hadn't seen Teddy in a while, as he wasn't one of Shawn's closest friends. I had caught word that he was once again kicked out of high school for sexist comments. He was a loser that was going nowhere in life, and I felt so ashamed of the sexual stuff I had engaged with him. My very-pregnant ex-best friend Ashley was also there, and for once, she wasn't naked and getting fucked. But I wouldn't be surprised if that changed soon.

They walked me down the stairs to the basement, where a camera was set up and aimed towards some blankets on the floor. "You're going to film me? You don't already have enough footage of me getting fucked and humiliating myself?" I complained.

"We want to capture the magical moment of conception on tape, of course," Shawn said with a laugh.

"Whatever. So where's the guy I'll be doing with it tonight?" Teddy stepped forward, and I eyed him with disdain. "Of course it's you," I said, rolling my eyes.

"I've impregnated you before, and I can do it again," he bragged.

"You didn't get me pregnant! That could have been anyone," I cried out, not wanting to admit to even myself that Teddy's sperm found their mark in me. I realized the camera had been turned on at this point, and arguing was only going to make things worse. "Let's just fucking do this," I said, accepting the situation.

We both stripped nude, reminding me once again how indifferent I had become to having my naked body captured on film. Teddy instructed me to lay on the floor as he wanted to be on top in order to 'really rail me.' As I positioned myself, the reality of the situation was hitting me. I was currently one hundred percent free of being pregnant. But I was knowingly about to have unprotected sex with a guy for the sole purpose of knocking me up. What the fuck was I doing? As Teddy started to climb on top of me with a full erection and balls full of potent cum, I pushed him back in a panic.

My audience of high-school 18-year-olds looked at me with confusion. "Isn't there anything else I can do? I really don't want to get impregnated," I said as a sweat started to build up on the back of my neck.

Shawn seemed to understand what was happening. "Having second thoughts about letting a teenager put a bun in your oven, Cindy? If you were really worried about that, then maybe you shouldn't have seduced us by the pool back when this all started," he said with a devious smile.

He was determined to keep up this lie about me starting all of this. "How about I agree to fuck you guys all you want, but with condoms or maybe after I get on birth control? It will be like before but without any risk of pregnancy," I pleaded. Saying those words out loud, I sounded like I was proposing to be their fuck toy, just like Ashley is. But at least I wouldn't be a mother to their children.

Shawn had enough and wasn't here to bargain. "You're free to make your own choice. Nobody is forcing you to do anything. But I am also free to make my own choices. And if I don't see Teddy unload into your pussy in the next ten minutes, I will choose to send your videos to everyone I know. No more negotiations. Either let Teddy in or walk away," he said calmly. I looked back and forth between his stoic eyes and Teddy's eager cock. Letting the videos out was the worst-case scenario. I've figured things out previously, and I can do it again. But I need time, and the only way I can secure more of it is to let Teddy have his way with me. I opened my legs up, and Teddy wasted no time penetrating me.

As promised, Teddy started humping me deep and fast. My pussy, embarrassingly, was ready and lubricated. Laying down here naked and being viewed by these guys, all while I accepted I was about to be impregnated, was making me subconsciously horny. It was an aspect of myself I didn't understand and didn't want to admit to, but true. Teddy, my current lover, was enjoying the sight of my tits bouncing from his thrust and paid my face no heed. This was typical of men that fucked me. I, meanwhile, watched his face intently. I wanted to see signs of when he was about to cum. I don't know why I did. It's not like I could do anything with that information, but the significance of this event was weighing on me. I hated this guy. He's the biggest loser I know and has no future ahead of him. But despite all of that, he was probably going to father my child.

"Ahhhh, fuck...." I moaned out as the head of his cock hit me in just the right spot.

This immediately directed Teddy's attention back to my face. "Someone's excited about getting impregnated by me again," he said.

"You didn't, ohhhh," I said, trying to object to his accusation but interrupted as his dick pushed even deeper into me. I looked at the camera, ashamed all of this was happening and being recorded. Teddy was going to get me to cum, all while he inseminated me.

My stomach tightened, and my legs squirmed. The feeling of the build-up of pleasure inside had become all too familiar to me. Worst, having this feeling occur with a guy you really wish it wouldn't be happening with. My mind raced back and forth, hoping he would cum and prevent this from happening, but then I realized what his cumming meant. This mental dilemma only exacerbated the situation, and soon I was yelling out in a loud orgasm, and the world went white for a few seconds. When I came to, Teddy was still going to town on me, and my mind gained clarity. But that proved to be a curse as I could fully appreciate what happened next. Teddy's face contorted, and he gave one last deep hump. My insides gained a warm, wet sensation, and I knew he had done it. This high school dropout deposited his cum into my fertile womb.

Teddy withdrew and stood over me, admiring this work. "I'll be back for more after you let those other losers have a turn with you," he said, referring to the other seven guys I would let try and impregnate me. The recording was stopped, and I headed home. I spent the night despairing over my situation and all the men I had fucked just to get to this low point. But I steeled my feelings and was prepared to see this through.

The boys would not give me any clue who the next man was. They only told me to show up the next night and be prepared. Shawn's parents seemed perpetually away. If only they knew how much sex was happening at their home. But I arrived and headed downstairs to the same area. I was expecting the next potential father of my children to be one of Shawn's friends. I imagine they were all anxious to get with me again. But that proved to be far from the truth. As I descended, my soon-to-be lover came into view. It was Mr. Ryan, the band director from the high school.

"Good evening, Cindy. I've been told I will be attempting to get you pregnant tonight," he said.

I took a minute before responding. But when I did, it was with high emotions. "You! You, of all people! Every time I've seen you, you've done nothing but slut shame me!" I yelled.

"What else was I supposed to do when I caught you on school grounds naked and having unprotected sex with one of our adult students? Not to mention when I ran into you at the school dance wearing that ridiculous dress. You were there with a barely legal teenager. I had to pry you two apart. You were practically having sex on the dance floor. I can only imagine what you did with him after you left," he said while shaking his head disapprovingly. His imagination was probably close to the truth, given what Teddy and I did after that dance.

"And yet here you are. Mister High and Mighty criticizing me for my actions. But you'll gladly impregnate a college girl. You're pathetic and a hypocrite," I scolded him. He took a deep breath before responding.

"I don't think a 23-year-old girl seeking out her fourth pregnancy in the past six months is in a position to question anyone else's decisions," Mr. Ryan said, looking smug.

I turned to Shawn with anger. "You fucking told him!" I yelled.

"I didn't tell him anything. I showed him your tape. That's all," he calmly explained.

"Why the fuck are you showing him the tapes! The deal was you wouldn't!"

Shawn disagreed. "I promised not to release them. Besides, who cares if your lovers see them?"

"Homeless men? Your uncle? Fifty people at once? Seriously Cindy. You are the biggest disappointment of a student to ever come out of our school district," Mr. Ryan said, continuing to give me judgmental looks.

As I thought of more insults to throw toward my former high school teacher, I remembered why I was here. Regardless of what I said, at the end of this, I would feel his cock cumming inside me. So, what was the point in continuing to argue?

"Well, this disappointment might just end up bearing your child. So shut the fuck up and get naked," I coldly replied. He watched me strip down, getting a much better look at my naked body than he did initially after getting caught having sex at the high school. I laid down on the floor but he told me to get on all fours. He wanted to take me from behind. I grunted but did as he asked.

The middle-aged high school teacher joined me on the floor, and I felt the tip of his cock press into the entrance of my womanhood before popping in. Another day, another man from my past gets to fuck me. As he plunged his rod in and out of me, he slapped my cheeks, making me jump a bit every time.

"Is the slapping needed," I said, looking back at him.

"I like seeing your ass fat jiggle," he responded. Hearing those words from a former teacher was too weird, and I refrained from talking with him any more during sex.

Mr. Ryan was well-endowed and stretched me out in a very pleasurable manner. But I managed to keep my emotions and other feelings under control, mostly, and felt his seed enter me without having embarrassed myself further by cumming on his dick. He gave me one last solid slap before withdrawing.

"I look forward to doing this with you again in the near future. Some women can take months to get pregnant, even having near-constant sex," he said as he put his cock away. The idea of fucking these guys for that long was insane. But what was even more insane was hoping I would get impregnated soon to end these sex sessions.

"Oh, and don't worry, Cindy. I promised these boys I wouldn't reveal what I saw in your confession videos. But I will enjoy masturbating to the videos of the bunny mask girl knowing that's you," he remarked before leaving and leaving me with that lovely image.

The following night, they had me meet at Don's house as, for once, Shawn's parents were going to actually be home. I realized these guys were going to have me do this every single night from here on until I proved I was pregnant. I still had six guys to meet and dreaded finding out who my third would be today. Opening the door to the room where the deed would be happening, I almost turned around and congratulated Shawn on who he picked. It was a masterful choice that really highlighted just how much of an idiot I had been. It was my creepy neighbor Trevor.

I hadn't thought about how he was involved in all of this in months. But the truth is, in a way, he started me down this path of sexual deviancy. This all started when Shawn and those boys got my bikini top, leaving me topless by the pool with nowhere to hide. I, of course, kept myself covered, but the guys used the threat of inviting Trevor over to get me to agree to expose myself. Trevor was a middle-aged man who was always watching me creepily. If I was mowing the lawn, he would be watching me from his window. If I was out for a walk, he was watching me. I'm sure he tried to get peeks through the fence as well when I swam in my parent's pool.

I foolishly agreed to show these guys my tits and more in exchange for keeping Trevor away from the situation. But despite all of that, Trevor got pulled in any way. But it's far worse. Before, if they had brought him over, he would have seen me topless but covered. Embarrassing sure. But that would have been nothing compared to now. I would be showing this creep my entire nude body, letting him touch it, and even have sex with him. I was more willing to show some horny teenagers my body than this man, and now I'm about to let him take a shot at knocking me up. Every decision I have made has been the wrong one, hasn't it?

Trevor was quiet but stared down my body as he always has. But he was doing it now with the anticipation that it would soon be his to enjoy. He started undressing himself, and I was met with the sight of his cock. Having sex with so many people in your life obviously means a lot of people get to see you naked. But sometimes, the oddest thing is seeing so many men's cocks. In all my days passing by his house, never did I think I would be in a position to ever learn the size and shape of his manhood. But here we are.

He motioned for me to join him in a state of undress. I have stripped in front of so many people that I have become relatively desensitized to doing it. But this situation reminded me of how embarrassing it was in the beginning. There were so many people I didn't want to see my naked body, but I ended up showing it to them anyway. Trevor was a different level of that. Facing no alternative, though, I endured. My pants hit the floor and were soon joined by my shirt, leaving me wearing only my underwear to cover myself. Just as I began to debate what to reveal next, Trevor pounced on me. Simultaneously his hand cupped my tits, and his lips found mine. My creep of a neighbor's tongue reached inside my mouth and contacted my own. I felt his bare, erect cock poke at my panties at the same time.

The shock of him being so forward prevented me from responding for a bit, but finally, I pulled myself away from him. Shawn immediately reminded me why I was here. "Cindy... be a good girl now."

My mouth was free, but Trevor continued to explore the feeling of my tits over my bra with his hands. "I don't need to be kissed to get impregnated by him. Let's just move on to it," I complained.

"No. I think we'll let your neighbor enjoy himself. Or do you object and wish to leave," he said in that semi-threatening tone I have heard him use so many times before. I let out a frustrated growl and stomped my feet on the ground.

I turned back to Trevor, who looked at me with lust-filled eyes. "Fine..." I muttered, and he reconnected our lips, and I soon felt his tongue back inside me.

Trevor's hands soon went about exploring the entirety of my body. From my tits to my back, from my ass to my pussy. All the while, he still hadn't elected to strip off my underwear. What was most infuriating was that he wasn't a bad kisser. I hated him and wished he was, but his lips didn't feel awful on mine, and the way he caressed his tongue against mine... I despised it but didn't at the same time. His hand took hold of mine and led it downwards until he placed it on his cock. Trevor still hadn't said a word to me, but I understood what he wanted and was rubbing it up and down. I was officially getting my neighbor off sexually.

As I did this, he withdrew his tongue from my mouth and undid my bra. He stared at my bare tits for a while as he enjoyed having me give him a handjob. He has probably imagined what my breasts looked like for years and likely assumed he would never get the chance to see them. Now, I was freely showing them to him. Even further, his hands took them in, and he felt the objects of his desire. But he didn't simply mush them like so many other inexperienced men did when they got access to my boobs. He caressed them. He massaged them. He was infuriating tender with them. Feeling my face become flush, I turned away. I was not going to give this jerk the satisfaction of knowing he was giving me a moderate amount of enjoyment.

Trevor directed me to the blankets on the ground. As I did so, I once again appreciated the camera that was capturing this event. My middle-aged neighbor didn't climb on me but positioned himself lower on me. I was still wearing my panties, so he started off by kissing my inner thighs and sometimes lightly licking them. I tensed my muscles up, hoping to avoid giving any indication to Trevor or the camera that my sexual stimulation was rapidly increasing. At one point, I let out a small gasp after feeling his tongue inch its way toward my womanhood. I stopped myself partway through but feared everyone had heard it.

Trevor finally slid my panties down my legs. I was kidding myself, hoping this would prompt him to finally start fucking me, but he didn't. He was going to go down on me. I considered talking him into fucking me by claiming I needed a cock in me right now or saying something else equally embarrassing. But in my experience, he would still give me oral, and all I would have done was make this video that much more shameful.

His tongue brushed ever so lightly along the outside of my labia, and I let out a groan that the whole room couldn't have missed. As he continued to push the strokes of his tongue deeper into me, my legs and arms couldn't help but squirm, and I filled the room with the sounds of my moaning and groaning as waves of pleasure hit me relentlessly. After yelling out my loudest moan yet, I complained in my head how good Trevor was a this. There was no way this loser got with women enough to have become this talented with practice. I never saw anyone else at his home. What the fuck was going on?

But my mind soon couldn't focus on that question and became inundated with sexual images as lust took me over. I visualized him continuing to fuck me long after I became pregnant. The thought of me with a large pregnant belly getting railed by him at the very pool this all started with. All the while, my other potential baby daddies lined up for their own turns. Not knowing who they would be, I imagined them to be almost everyone I had fucked and even a few I hadn't yet.

Back in reality, Trevor introduced two fingers inside my pussy. Feeling them penetrate me was all it took, and the waves of pleasure were replaced with a tidal wave that rocked my world. "Fuck my pregnant ass!" I yelled out as my back arched up, and I felt pure ecstasy travel down my spine. As I came to, Trevor was pumping his cock in my pussy. I made eye contact with him, tilted my head up, and kissed him before my head fully cleared, and I remembered I didn't actually like him despite his sexual abilities. I pulled my lips away and turned my head.

I expected him to cum quickly, but it didn't happen. He was humping me at a vigorous pace but seemed to be getting no closer to seeding me. Despite not having a particularly large cock, it was doing a decent job, I will admit. The way he was thrusting was producing an enjoyable feeling inside me. I was still recovering from the orgasm his tongue gave me, so I wasn't sure how much of what I was feeling was from me coming down from cumming or from his cock in me. Right then, my face tensed up, and my hands grabbed hold of the blanket we were fucking. His dick had sparked something inside me that took me completely by surprise.