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.

 

The Convenient Oral Agreement

For the first several weeks (he will still do this sometimes) Neighbor Boy messaged me to negotiate the terms of our FWB. He has asked what I’m willing to do, what I like, and what he can expect from our arrangement. I never would have thought that this type of communication and negotiation would be necessary in a FWB situation, I usually just let things play out and let the terms unfold over time, but somehow this has worked for us. Because of this, not only were we aware that this was a sexual arrangement between neighbors, but we knew from the start what that meant for us.

The gray area that comes with the beginning of a new relationship came briefly at the start, but left just as quick. It was all of this conversing that created this mutual understanding from the get go.

One of my favorite clauses of our arrangement has to be convenient oral sex. This is something we came up with early on. Neighbor Boy was asking what to expect from our sessions. He was wondering if every time had to be an entire evening or if quickies could be on the agenda. During this, he then proceeded to inquire about blow jobs, and the rest is history.

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Just like that, convenient oral was born. He said he’d be home around 6:30pm or so. I had plans at 9pm, so this would work perfectly. He told me to have my vibe and anal beads on standby, tonight was all about me. He was running late (something I expect of him almost always now). You would think an hour should be plenty of time, but I have a very complex vulva and depending on your style, it could take a while to crack until you learn my body well… This was his first time really delving into eating me. He ate me briefly before, but not a full blown attempt. The later he was running, the less time there was for him to make me cum and I was eager to see what he had going for him.

As 7pm passed. Now over a half hour late, I texted him to see where his ass was. He explained he was just getting home from work and would be up shortly. He came up around 7:30, giving us about 45 minutes until I had to get dressed and ready to head out for the evening. Once again, you would think this is plenty of time, but I have a very tricky clit. Unfortunately for me, my clit is quite small and recessed pretty high under my clitoral hood. On top of this, direct clitoral stimulation is what really does it for me, which is one of the main reasons I got my vertical clitoral hood pierced.

When he came up, he sat next to me on my bed. Neither of us made a move right away. There was kind of an awkward pause. Even though we had already fucked and there was this ongoing dialogue about what we expected from our sexual relationship, this pause got me a bit anxious. I have fucked and have had my pussy eaten numerous times before by various guys in a variety of situations and have gotten over that nervous first time phase and into this confident stride with every guy I’ve interacted with the past couple years. But somehow, this very instance, a few sexual encounters into our budding relationship, I felt vulnerable.

To break the silence, I asked, “What toys did you want me to grab?”

He confirmed, “Your favorite vibe and anal beads.”

I got up, grabbed the toys out of my dresser, and made my way back to bed setting the toys along side us. The awkwardness subsided some, but there was still some slight fumbling. He went in to kiss me. This eased everything a bit more, and as the kiss prolonged, he started to strip me naked, rubbing his hands down my back and grabbing my ass. His full lips pulled away from mine as he worked his kisses down my neck, grazing my collar bone, and tease my nipples with his tongue.

Laying me down, he spent some time on my nipples as he worked his hands on my inner thigh. He then sat up, grabbed the vibe, and started to rub it on my clit and teasing my vagina, watching my face in anticipation. I smirked, and told him, “Add some lube.”

Confused, he questioned me, “You’re soaking wet though.”

I grabbed the toy from him and explained, “I know, but silicone, no matter how wet I am, feels better with lube. It makes it slide in and out much easier and takes away any potential friction.” I then rubbed the toy against his skin to show him how the toy almost pulls on your skin due to friction, added some lube and showed him how slick it became.

I handed the vibe back to him to let him play some more. The toy was an Ina Lelo vibe. Not necessarily the optimal pussy eating vibe, but he insisted I grabbed my favorite vibe so I did. Being a classier rabbit style vibe (it’s more sleek and doesn’t have the “cute” rabbit ears), it’s a duo motor vibe for g-spot and clit stimulation.

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Well as he started to insert it, I instantly jumped back, “Ummmm… that part isn’t meant for my ass! That’s a clit vibe.”

“Sorry, my bad.” He corrected the vibe, and we continued.

As he slid the vibe in and out and rubbed it against my clit, I started to ease into it more. He then went back to kissing my nipples as the toy worked it’s magic some more. I stopped him, “I love my toy, but wasn’t this supposed to be convenient oral?”

He looked up at me and pulled out the vibe, “Turn around and get on all fours.”

I smirked and obeyed. He kissed my back and worked his way down my ass cheek to my inner thighs, then licked my pussy from behind. A very hot move, not a go-to for me, but hot nonetheless. I leaned forward and let him lick and suck on my lips for a few minutes. He then demanded, “Now sit on my face.”

I let out a slight giggle, “Ok, but if you want me to cum, you’re best bet is to have me on my back, something about being able to fully relax brings my orgasms out easier.”

“Just do it,” he insisted as he repositioned himself to lay down.

I listened, swung my leg over his face, placing my clit on his mouth, and pressed my arms against the wall, using it as a prop to push against as I rode his face. His tongue slid up and down between my inner lips. As I pushed my hips back, his tongue would circle above and below my clit pushing my piercing side to side, directly stimulating my clit. When I pulled my hips forward, his tongue would barely graze the entrance of my vagina. Back and forward I moved my hips and let his tongue explore my soaking wet pussy.

Several minutes of riding his face was enough. As hot as it was, I still knew this would not get me to cum.  I rolled over, swinging my leg over his body, and laid down, “I’m not cumming by riding your face.”

“Fine,” he agreed, “Where are the anal beads?”

I handed them to him with lube. As he squeezed out some lube on his hand and slathered it on the toy, I gave him instructions, “I don’t know how much anal play experience you have, but with beads, for me, they aren’t an aggressive in and out toy. Insert, twist and turn a little, maybe pull out slowly and reinsert some, but nothing too excessive. That is until the end… pro tip, as I’m cumming pull the beads out.”

He was a bit cocky, “I’ve done plenty of butt stuff, don’t worry.” His lack of knowledge on my vibrator had me a bit doubtful, but he has shown quite a bit of skill with his tongue, so I let him get to work. He slowly inserted it bead by bead; every bead larger than the one before gave me a slight tinge of pleasure.

As the last bead was inserted, he looked up at me, smiled, then slowly brought his mouth to my clit, licking it, playing with my piercing with his tongue, and making intense eye contact for several long seconds. It has become apparent, he is one of those guys that loves to watch a girl react to everything he does. Although this adds more vulnerability, it was kind of hot.

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With one hand, he played slightly with the beads, the other hand he grabbed my vibe and slowly moved it in and out with the clit vibe rubbing side to side beneath his tongue as he ate me. This was a fucking mind blowing trifecta of pleasure going on. All the stimulation was super hot, but my vulnerability from before kicked in again. I knew how eager he was to please me and that intense stare, although hot, pulled my head away from the action and into a headspace where I was thinking more about his eagerness to please me and overthinking my orgasm.

Everything he was doing was so fucking good, but I needed to snap out of my thoughts. I threw the pillow from under my head aside, leaned my head back, and closed my eyes. Deep breaths in and out, refocussing my thoughts on every flick of his tongue on my clit, the beads in my ass, and the vibe in my vagina.

Inhale, one, two, three, four. Exhale, one, two, three, four. Repeat.

As my mind cleared, my hands started to go numb, then my forearms, then my feet. This was one of the most prolonged orgasm I’ve had. Everything was tingling awaiting a full body release. Literally minutes of numbness and my body still didn’t succumb. It was almost too much stimulation.

I kicked the arm that was controlling the vibe, “Take it out.”

He listened. As the vibe came out, the numbness turned to a tingling sensation, my breathing got heavier, my back arched, a feeling of ecstasy took over. I felt my orgasm coming, “Pull the beads out now!”

As he pulled the beads, tongue still on my clit, my orgasm released, my vagina contracted, and my entire body tensed up with pleasure. Once I came down from that high, I pulled him up from between my legs and kissed him, still catching my breath. “That was fucking hot.”

He then got up, but as he did, I pulled on his hand to sit him back on the bed. Although I had plans, I wanted him so fucking bad. I wanted to blow him and fuck him all night. I went to reach down his pants to grab his cock, he pushed away my hand, “Tonight was just for you, convenient oral at it’s finest. I will get mine soon.”

He wouldn’t let me. I kept trying and he kept pushing me away even though he was rock hard. “I do like how much you want to blow me though,” He added as he got up again to leave. I got up and kissed him, pushing my naked body against his, lingered for a moment, and then let him out.

I looked at the time, it was 9:15pm, I was already late for my plans. I hurried up and got dressed and booked it to the bar.

Convenient oral. Best term to our agreement yet.

Yours Truly,
Kallie Pygus