Baby Steps to Build Trust

Since Roid Douche, anal sex was off the table. I couldn’t bring myself to be comfortable with the idea of letting any guy penetrate my ass again. It took a lot of time and trust for me to even allow any light anal play from my next serious boyfriend, The Man Child (who I dated for six years). In those six years, he asked about anal from time to time because it was something he wanted to try with me, and I kept turning him down. He’d ask why I didn’t want to try it, I explained I’ve tried it before with Roid Douche, but didn’t like it. I didn’t inform him of the rape at that time.

Over the first few years of dating, as The Man Child tried to ease me into the idea by incorporating light anal play from time to time into our sex, he brought it up again, asking if anal sex would ever be on the table. I then explained what had happened with Roid Douche. We had a lengthy conversation that involved me crying about it, him consoling me, and him saying that he’d kick Roid Douche’s ass if he ever came across him. He also threw out there that if anal sex was ever something I would want to try again, he’d obviously be down, but understood why I haven’t wanted to all these years so far.

The Man Child stopped asking about anal since I told him about what happened with Roid Douche, but he still tried to incorporate anal play in our sex. I knew he was secretly hoping he could get me interested in anal. I enjoyed a finger and some ass eating every once in a while, but I was unsure if I was capable of enjoying a cock. I was conflicted. I felt some sort of pleasure from the stimulation of anal play, but I got anxiety thinking about anal sex. I wanted to try it again, but I also didn’t want to relive my experience.

Eventually, probably about four years into dating The Man Child, almost five years after the Roid Douche incident, I told The Man Child I wanted to try anal. He was ecstatic. He did everything right. He incorporated lots of foreplay and oral and warmed me up for anal with some analingus and fingering my ass. He got the lube out and prepped my ass and his dick. He told me he’d go extra slow and all I needed to do was relax.

He got his dick in about an inch and my anxiety kicked in, I started to clench my ass and it started to hurt, and I freaked out, and told him to stop. I teared up and shut down. The Man Child was a bit frustrated, but understanding of the circumstances. He held me, and comforted me, and tried to ease my anxieties. We tried one more time since then, but same thing happened. I couldn’t go through with it and he was ok with not trying anal ever again.

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After I broke up with The Man Child, almost three years ago now, I have slept with a lot of guys. Many guys have asked about anal, I tell them it’s not happening because I’ve tried and don’t like it. Every once in a while, a guy will slip a finger in or try to lick my ass and if I show any amount of enjoyment, they push for anal sex. I refrained from telling them what had happened with Roid Douche, but I explain to them that licking and fingering an ass is completely different than having a dick fuck your ass. I say something like, “A finger is much smaller than your dick, I’m ok with and enjoy a finger from time to time, but a dick is a no go. I’ve tried it and don’t like it.” And some of them push it and some of them let it go, but I stayed consistent with my word and wasn’t trying it again.

About a year ago, there was a moment of pure bliss I felt when a guy was eating my pussy and fingering my ass and vagina at the same time. The orgasm was intense and I wanted to recreate that feeling. I bought a small vibe for my ass, not much thicker than a finger, and began incorporating that into my masturbation. Shortly after that, I bought some gradual anal beads, the largest bead was about two fingers thick, and played with those by myself and introduced them with some guys to add to our toy fun.

And then Neighbor Boy came along. He had a good amount of persistence when discussing what is okay under our terms of sexual agreement. He’d push for cumming in my mouth and no condom use, both no goes. He pushed for photos and video, shot down. He pushed for anal, I turned him down. I explained to him that a lot of those things are not for guys I’m just fucking. I have to trust someone before I allow for them to cum in my mouth or go condomless, get photos or video, or before we could even put anal on the table. He then asked how he could build that trust with me. I told him it would take time, communication, and also an eagerness to please me extra in the bedroom.

In those early months of our arrangement, we talked most days and had lengthy conversations about sex, our likes and dislikes, our experiences, our desires, and we communicated when we’re sleeping with other people. We were 100% honest and upfront to one another. He made it a point every time we fucked to try to make sure I was pleased with our sex and we would have discussions usually the day after about it, he’d ask what I enjoyed about it and if there was anything he could have done differently. He took my directions and our sex kept getting better and better.

Over those months, he worked for it. He was eager to build that trust with me so he could get to cum in my mouth, get photos and video, and get anal sex. He was doing a pretty damn good job at it too. The more eager he was to please me and the more effort he put in, the more eager I was to please back. I let him cum in my mouth; something very few guys get to do because I have an aversion to cum. I sent him photos from time to time; I don’t send nudes to most guys, another Roid Douche story behind that one. And then anal… well he still wasn’t getting anal.

We discussed anal sex time and time again, and I told him I’ve tried forever ago but wasn’t into it, but I didn’t tell him about Roid Douche. He then brought up the anal beads and how I like those, and I explained that those are still smaller than a cock, so it wasn’t quite the same still. He kept telling me how he’d make sure I was enjoying it, and I wanted to try, but I still had this intense hesitation.

That’s when I decided to order a large Njoy butt plug. Larger circumference than the anal beads, but still smaller than his dick girth, it would be a good stepping stone to add to our sex to get me more at ease with anal. When it arrived, I kind of got giddy. It was a new toy to play with and I was excited to try it out. Neighbor Boy and I were already planning on hanging out that evening, so I told him I had a surprise for him. When he came up that evening, I unboxed the shiny new toy. I was turned on just by the idea of trying it out.

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Keeping it bed side, he got me warmed up. We made out, he worked his way down my neck to my nipples, to my clit with his tongue. He ate me a good while and got my vibe out, getting me extra worked up, and when I was nice and soaking wet, he grabbed the plug. Lubing it up, he inserted it slowly into my ass. A slight tinge of pain hit me, but after the head was inserted, it was all pleasure. He went back to eating me and playing with the butt plug.

I was really enjoying the feeling of the butt plug, but at the same time, I kept getting in my head too much. The pleasure was great, but it was difficult to fully let loose. I repositioned myself and he presented me with his throbbing cock. I took it in my mouth and blew him while I held a vibe to my clit and he played with the butt plug. The vibe and plug sensation while simultaneously blowing him got me extra hot. Soon enough, I was cumming from the combination and trying to keep his dick in my mouth as my body unleashed an intense simultaneous anal/clit orgasm.

Shortly after I came, he grabbed a condom and began to fuck me, butt plug still in. I was double filled and loving it, but it was almost too much. I was still fresh from the recent orgasm and now the butt plug was becoming uncomfortable. Not long of this and I had him stop so I could remove the plug, and got back to fucking.

The next morning, he asked about my thoughts on the butt plug and what I liked and disliked about it. He wanted to know what was working and not working so he could take that into consideration moving forward. I like that about him, he actually asks questions and makes sure what he’s doing is good for me. He doesn’t assume that everything he’s doing works, he wants to learn about what gets me going and wants to make sure I’m enjoying myself.

Since then, Neighbor Boy, although he has been insistent on using the butt plug from time to time to warm me up to anal, didn’t push anal sex any more. He knew that in time, if I wanted anal, I would make it happen. As I told him, baby steps to ease me into it and to build trust and eventually anal might be possible.

Trust, communication, and an eagerness to please are all important elements in any relationship.

Yours Truly,
Kallie Pygus

 

*** Note: in case you’re wondering timeline, I got the Njoy butt plug about 10 days before I got my Triangle Piercing, so sex and oral were still ok.

 

Roid Douche: A prick from 10 years ago…

To understand what’s to come, I need to fill you in more on my past. A little over ten years ago, I was dating Roid Douche. When I met him, I was lured in by his muscular build, badass demeanor, and found his sarcastic ass remarks comedic. Over time I realized he wasn’t what I painted him to be and he was really just a fucking prick that I was enamored with because teenage hormones.

Perhaps one day I will tell the full story of how I met him and the ups and downs, but for now I’m only filling you in on how he has impacted me to this day and how recent events that brought memories of Roid Douche back.

We had been dating a few months. We had been saying “I love you.” We spent as much time together as possible. We were inseparable. That’s how it started, but really my perception was skewed by hormones and infatuation. He was the jealous type. He was controlling. He was manipulative. He was a bipolar mess of rage.

Let’s focus on the manipulative and rage aspect for now, I will go in depth another time about the rest. A few months in, a couple weeks of “I love you” later, and still no sex to be had, he started to threaten to break up with me because I was too prude to fuck him. He started to show his true self, but I was in love and didn’t see it. He kept pushing the “I love you” card trying to get me to spread my legs and I kept saying I wasn’t ready and he kept telling me he didn’t know how much longer he could wait.

For my sixteenth birthday, I convinced my mom to let me rent a couple hotel rooms in the city for me and my friends with my sister and sister’s boyfriend as the chaperones. The plan was to go shopping with the girls then meet up with the boyfriends and everyone else at the hotel to drink and party all night. While the girls and I shopped, we each found little black dresses to wear for the hotel party and got all primped and ready for the night.

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We made our way back to the hotel, got started on the drinks, and the boyfriends and more followed soon after. We had all the boys drooling over our dolled up looks and little black dresses. Roid Douche couldn’t keep his hands off me. Maybe it was “love,” or maybe it was his possessive nature seeping out as there were other guys giving me hugs to wish me happy birthday.

A few drinks in, the party hardly started, and Roid Douche was getting anxious. His hormones caused a raging mess and he became frustrated as I kept trying to hang out with everyone. It was my birthday party after all and I was the guest of honor, why would I leave the party early? He kept insisting, “Let’s go back to our hotel room to slip you out of that little black dress…” I kept denying him the pleasure.

He eventually got angry and walked out. I followed him to the hall. He threatened to leave, he said he thought he’d get some alone time with me in our hotel room, but I was too busy with everyone else. Obviously the right response to this would have been to tell him to fuck off as it was my birthday and he could suck it, but instead it turned into me tearing up and us fighting, and him apologizing, and then me finally agreeing to go to the room.

I went back into the room and said good night and thanks to a few people, then slipped back out to meet up with Roid Douche in our hotel room. It had two queen beds. We were to share it with my friend and her boyfriend but they were still back at the party. We quickly got to making out, feeling up, and stripping down.

He moved his way from my mouth to my neck down to my nipples and trailed his way to eat me. This was a first. We have made out, he has felt me up and fingered me, I have given him hand jobs, but oral wasn’t something we had done before. Even through all his begging and pleading for sex, eating me out was never on the table.

Tonight was different. He wanted to warm me up for sex. It was obvious. He was fine, nothing spectacular though as we were in high school and although he wasn’t a virgin, his lack of experience showed. Regardless, I was liking it enough. I laid back and closed my eyes and was taking in every lick and kiss, but only a few minutes in and Roid Douche came up from between my legs all huffy, “What’s wrong? Are you even enjoying this? You aren’t cumming yet!” As if I did something wrong. As if I was broken. As if I was incapable of being pleasured by his almighty tongue.

Trying to calm him, I pulled him in to kiss and tell him I liked it. Instead of him going back down to keep eating me, we began making out and then he pushed to get his dick wet and I denied him. The brief moment of calm was overruled by anger again. I couldn’t win. He threatened to leave again and I cried and we fought and finally I convinced him to stay because it was my birthday and it was 3am and there was no way for him to get home. He agreed, but said he was having his dad pick him up first thing in the morning. We went to bed with him angry and me upset and hardly spoke the next morning and he left as he said he would.

As he got up and left early the next morning, my friend and her boyfriend (who must have slipped into the room sometime recently) woke up still very drunk. “Why is he leaving?” my girl asked. I told her he had a family emergency and that his dad came to pick him up. She tried to pry because I was obviously upset, but I tried to play it off as a headache from being hungover. We all fell back asleep and nothing more was said.

After a few days of apologies and I love you’s we made up and were back to normal. And a few more days after that, I caved. I thought I loved him. I thought that maybe all this tension and anger was from us not having sex. I let him take my virginity, on the beige pleather couch, in his garage (aka his man cave), in the dead of winter, freezing cold.

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He kissed me briefly, hardly any warming up or foreplay, grabbed a condom, spit on his hand to rub it on his dick, laid on me missionary style, and pushed his cock into my tight vagina. I laid there, staring up at the ceiling over his shoulder, trying to get my mind off the pain and hoping for it to end soon. A few minutes of him gyrating on top of me, he came. After he finished, he pulled his cock out of me and realized among the bloody mess from my torn hymen that the condom broke. Just my luck. First time in and I already have a broken condom story…. two plan B pills and week or so later, sex became more and more regular in our fucked up love story.

A few months later, all the sex, and oral, and exploring of some basic kinks and fetishes, the fighting never stopped and his bipolar roid rage continued. He kept finding things to threaten to leave me over and kept using how much he loved me to get me back. The newest thing he was pushing was anal. He wanted that new tight thing to de-virgin and my ass was calling his name.

He pushed and I told him no. He told me how much he loved me and if I loved him I would give it to him. I still told him no. He continued to push and threatened to leave because I didn’t love him if I didn’t do it. I didn’t want to lose him. We were in love. I was blind. All I could see was the drops of good moments in a vast sea of abusive misconduct.

I caved. I bent over that same beige couch in his garage, presenting him with my ass as he demanded. He spit on his hand, rubbed his cock, and thrusted into my ass. Only one thrust in and I was in too much pain to let it keep going. I wailed an ouch in pain pushing him off me. I pissed off the beast, “What? You let me get started and can’t even let me finish?”

I tried to tell him it hurt and I didn’t want to keep going. He was still angry. “Just let me finish, I will do it slowly. It won’t take long, your ass is so tight.” He pushed me back on the couch, spit some more on his dick, pinned me down and shoved his cock in me and pushed in and out slowly like he said he would, that didn’t help ease the pain. Even as I said stop and no, and as tears ran down my face, and tried to push back, he was too strong, he held me down and he continued to fuck my ass until he came in me. He then pulled out and wiped his dick off.

Still crying, hurt, and shaking, I laid there on the couch withdrawn from Roid Douche. He quickly came to my rescue and wiped my tears with his hands, kissed me, held me and apologized while simultaneously saying it was my fault he got so wound up and that he loved me and didn’t mean to hurt me and that it wouldn’t happen again.

I should have left him long ago. I should have never let it go as long as I did. I should have never dated him in the first place. I wish I would have seen it sooner. I wish my teenage hormones and “love” wouldn’t have blinded me. If only I could go back and take the day I met him back I could avoid giving the manipulative prick my virginity. I could have avoided him manipulating me into anal and avoided the continued anal rape.

From the outside, it was obvious to many of my friends and family that the relationship wasn’t healthy, but no one knew how extremely fucked up it was. I hid how shitty he truly was. I loved him. I didn’t want to lose him. I stayed with him for way too long, and 13 months in, I finally got the courage to end things.

I’ve only told a few people about what happened behind the scenes of our fucked up relationship, now whoever is reading this is part of that small few who know. At least you get the gist of things based off those few instances of emotional and sexual abuse, now multiply that by 13 months. Maybe I will fill you in more later, but those details are necessary puzzle pieces to tell you more about recent events.

Now that the seal on all the feels has been unleashed, there will be more to pour out soon. Until next time…

Yours Truly,
Kallie Pygus