Birthday Sex Marathon: Day 3

Thursday, December 8, 2016

I woke up to a voice message from The Australian; hearing his accent was a nice way to start my morning. He’s been consistent and true to his promise. So far we talked pretty much all day every day, we shared things about our childhood, our hopes, our dreams, and kept up with our flirtatious banter; we shared things that I usually avoid talking about with most guys. It’s only been a week and I was beginning to miss him, a guy I just met briefly for two nights hardly a week earlier… but alas, he was on the opposite side of the world in Australia for the next few months and there was no promise of coming back to Chicago permanently (or at least semi-permanently).

Mixed in with my snaps and Whatsapp messaging with The Australian, I got a message from Neighbor Boy, he asked for my review on his performance on Day 2 of my Birthday Sex Marathon. He did quite well, he teased me till I was begging, repeatedly brought me to the brink of orgasm multiple times, and once he finally got me to come, he pulled out and left me craving more. His game plan, as revealed the night before, was to do everything to keep me begging for more the next few days and it was working. He then asked what I wanted more of; I told him the obvious, more oral sex.

That evening, he told me when to take my toys out and demanded I start playing with myself as he would be up soon. I sent off my “Day 3 of my birthday marathon…” snap to The Australian and got my toys out. I started off slow, set my vibrator on the lowest setting and ran it down my body starting at my nipples, circling them gently, then down my torso working my way closer and closer to my vulva. As I approached my inner thighs, the temptation to give in was magnified.

My clit tingling, I finally caved and brought my vibrator to it, but only lightly, running it up and down my inner lips tickling my clit with every upward stroke. I was on the brink of coming when my bedroom door swung open; it was Neighbor Boy. Resisting my orgasm, I set my vibrator aside.

No words exchanged, he dove face first into my soaking wet pussy. I demanded more oral and he delivered. He brought me back to the brink of coming, then stopped. He looked at the toys and handed me the butt plug. I lubed it up and slowly inserted into my ass. He got back to work, licking my clit and playing with the plug. The sensation of the plug mixed with his tongue on my clit pushed me over the edge and my body gave in, my breathing got heavier, my back arched, my vagina contracted.

Neighbor Boy slowed down, and as the final contraction released, he looked me in the eyes, crawled up, and kissed me. “Better?”

“Yes,” I smiled.

We laid there for a second, then after I came down from my orgasmic high, I proclaimed, “Fuck me in the ass.”

He smiled, agreed while demanding, “Sure, but blow me first, get me hard.”

I crawled backwards down his torso kissing him down his chest and took his cock into my mouth and blew him. A few minutes in, he was worked up and ready, I got up and handed him a condom and lube. I laid next to him anxious. I was nervous yet excited for us to have anal sex. This was the first time I was fully eager and willing to let a guy enter my ass with his dick since ten years ago when I was raped by Roid Douche.

As he put on the condom and lubed up, he asked, “Do you want to be on top? Or bottom?”

“Bottom, missionary, it will help me relax more,” I explained as my anxiety was kicking in more. I then reminded him, “Take it slow, also, no promises we can finish.”

He nodded, “I know, I’ll take it easy on you, don’t worry.” He then squeezed some more lube on his finger and slid it into my ass.

We laid missionary, we kissed, with one hand I held my vibrator to my clit and with the other I guided his dick towards my ass. With a deep breath in and exhale, he slowly inserted his cock. I focussed my energy on kissing him, the stimulation on my clit and relaxing my ass. My heart pounded.  A few minutes in of him slowly sliding in and out of my ass, we switched positions, doggy style now. He entered from behind slowly. As he slid in and out, he added some light spanking and hair pulling, something I’d usually allow, but I panicked. I stopped him, I rolled over and he laid beside me.

He asked, “Is everything ok?”

I started to tear up, “I’m fine. I was enjoying it, it’s not you…” I paused.

“Are you sure?” He asked.

I sat up and the tears flooded out turning into full on crying. He pulled me towards him, holding me, trying to soothe me as I had a breakdown. “I’m sorry,” I explained, “It’s just difficult for me. I’m enjoying it, but it’s also overwhelming.”

He made a smart ass remark, “Dick so good she cried,” but quickly realized that wasn’t going to work in this situation. He then took it down a notch, “What’s up?” And that’s when I fully unleashed the tale of Roid Douche to him. He kept trying to comfort me, yet the whole scenario was awkward as fuck. He tried to be sympathetic, it worked a little, but he kind of failed after the fact.

Once the crying subsided, he left to go back down to his room, leaving me alone vulnerable in my room. He then messaged me:

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Really? “This gonna be all worked out for tomorrow or what”? What type of question is that after I have an emotional breakdown and spill everything about being raped? To top it off, he still pushed trying to get his dick wet and gave me a maybe for my official birthday sex. He was failing on his response and he wasn’t getting it.

Having anal sex was a big deal to me and I still don’t think Neighbor Boy fully understands this.

Yours Truly,
Kallie Pygus

Birthday Sex Marathon: Day 2

Wednesday, December 7, 2016

I woke up to a snap from The Australian of him chilling in his pool bragging about the nice weather, a “good morning” text from The Chef, and a Facebook message from Neighbor Boy asking about my Birthday Sex Marathon: Day 1. The attention these boys are paying me definitely helps show the love for my birthday week. I send The Australian a sultry “good morning” snap of me near naked in bed, ignore the good morning text from The Chef until later in the afternoon, and spill all the disappointing details to Neighbor Boy about Day 1 and tell him he better make it better that night for Day 2 of my birthday sex marathon.

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In our messaging, Neighbor Boy confirmed he’d clear his schedule for me tonight through Saturday so my Birthday Sex Marathon could commence. Neighbor Boy also told me he’d be ready by 9pm tonight, but expect a message from him earlier to tell me when to start playing with myself. I’ve hardly used a vibrator in 10 weeks, and the few times I did it was limited because my piercings were too tender. I was getting wet thinking about my toys. I told him I might just have to pull out my toys right then, he told me I had to wait till he gave me directions to use them, I obeyed.

Not long before 9pm, I snapped The Australian a selfie saying “Day 2 of my birthday marathon…” and he responded with “Have fun” and several heart eye emojis.

As 9pm struck, still no message from Neighbor Boy. The anticipation was killing me. I messaged him, asking if I should start playing with myself. He told me not yet. I waited. He finally told me to start playing with myself, told me to put on my nipple clamps, start using my vibrator, and have my rope and butt plug on stand-by. I got started and sent a photo as proof and also to get his ass up to my room quicker. He still took his sweet time.

I texted to tell him how close I was to coming, he told me I wasn’t allowed to yet. Shortly after that, he opened my bedroom door, told me to set my vibrator aside, and began to tease me. He kissed me lightly, and pulled away. Grazed his lips over my nipples, but left them just as quick. Brushed his hands all over my body, but didn’t quite caress me. He kissed my inner thighs, but wouldn’t kiss my clit. He meticulously tortured me with every move he made.

He then lubed up the butt plug and had me put it in. Nipple clamps on, butt plug in, body riled up from all the teasing, I was dripping. He dove in and ate me, licking my clit up and down as he played with the plug. My body stimulated on all fronts, I was about to climax just minutes into getting eaten, and he stops, stands up, and goes to exit my room.

I jump up, and pull him from the door, “Where do you think you’re going?”

“It’s all part of my plan, I’ll see you tomorrow,” Neighbor Boy said with a cocky smirk.

“Fuck no you aren’t,” I explained, “It’s my birthday, I’m supposed to get birthday sex.”

“It’s not your birthday yet.”

After a few minutes of this discussion, I basically begged for him to keep going, he finally let in, all he wanted was to hear me beg for him to make me come. It worked. He then tied my wrists together, vibe in my hands by my clit, flipped me over and tied the rope around me, forcing me to keep the vibe by my clit. He grabbed a condom, put it on, and he entered me from behind. Every time he pushed in, his body would press against the butt plug, my clit still tingling from the vibrator, my nipples being pinched by the clamps. All of this had my body stimulated to the max, but right as I began to climax, he pulled out, cutting my orgasm short of what it could have been.

“You ass!” I was frustrated, I came, but he intentionally slid out right at that moment to throw me off. He smiled that cocky smirk. He knew what he was doing.

He untied me, set aside the vibrator, took the clamps off, butt plug still in, and we laid there for a bit. “We should try anal,” I said.

“Not tonight,” Neighbor Boy responded and then sat up, got out of bed and started to get dressed.

“Where do you think you’re going?” I questioned, confused about his response to me offering anal sex.

“I’m hungry and you told me earlier you have to wake up early tomorrow and might not want a sleep over,” he then added, “You’re welcome to come down and eat and hang out if you want.”

“Fine, I’ll be down in like 10 minutes,” I responded.

He left, I got up, went to the bathroom, took out the butt plug and washed it, went back to my room, took a sexy snap and sent it to The Australian saying “Wiped, passing out! xoxo,” got dressed, and made my way downstairs. Neighbor Boy was making pizza rolls and chicken rings; obviously he doesn’t fit my dream man criteria of someone who knows how to cook. I laughed and poked fun at him for his food choices. He told me to take it or leave it. I was hungry so I stayed. We took the pizza rolls and chicken rings to his room.

We ate, cuddled, and watched some Netflix. Not long into this, Neighbor Boy was drifting off and as he fell asleep, he started to snore. I really did need to wake up early, so I got up, and went upstairs to my bed. The joys of a fuck buddy who lives downstairs from you is your bed is never too far away.

Yours Truly,
Kallie Pygus

Letting Go

Shortly after I bought my njoy butt plug (See Baby Steps to Build Trust), I got The Perfect Triangle… piercing which was not so perfect. I had 8-10 weeks to heal. That meant 8-10 weeks of no oral sex, and being extra cautious of my new piercing. During this time, Neighbor Boy insisted on using the plug regularly. If I was blowing him, he’d tell me to “Grab the plug.” If we were fucking, “Grab the plug.” If I we were taking out my vibes, “Grab the plug.” If we were sexting, he’d tell me to get out my favorite vibe and “Grab the plug.” He didn’t quite push for anal, but he was eager to get me into the sensation and the idea of anal.

Almost 8 weeks of this and it was working. I was really getting into the plug so much so that I started using it on my own time as well. Sometimes, I would get wet and worked up just thinking about it. I craved the full feeling the weighted plug gave me. As 8 weeks came to a wrap, I started to bring up anal to Neighbor Boy, telling him we should try it when my piercing is healed.

There was only a short window of time anal was going to happen. I wanted my triangle to be healed, but shortly after my triangle was healed, I was getting my VCH repierced. Having oral sex on the table pre-anal was important to me. I wanted to make sure I was fully satisfied and at ease before letting him penetrate my ass.

It was late November. We were messaging as per usual, probably even sexting some, almost like our foreplay before we were supposed to hang out that evening. I brought up that we should try anal that night. He was excited, but told me he expects me to have my plug in and vibe going before he got there so I was extra worked up already.

Although I was excited, I was also anxious about the situation and him telling me to get myself ready before he got there was a huge turn off and quite aggravating. Him telling me to start playing with myself before he comes to fuck me can usually be hot, but this time, because it was to prep for anal, it was more upsetting than a turn on.

I told him I wanted him to come eat me and crank up the foreplay and ease me into it. I explained to him I’ve had a bad experience with anal before (kind of alluding to what happened without directly saying I was raped by Roid Douche yet) and that him helping me be comfortable and relaxed beforehand would be very important.

Well… this conversation quickly went south. I was getting more and more anxious and upset and kept pushing what I wanted and he got frustrated and said that “It’s starting to sound like work and I’m not really feeling it for tonight anymore.” Which of course pushed me over the edge and the night was canceled, at least for the moment.

Because of this, I met up with my gay hubby. We went and got coffee and I vented. The more I vented, the more I realized how stupid the argument was. Yes, he was being an asshole, but my anxiety and frustration wasn’t fully explained to him. I was basically freaking out and he (unaware of what actually happened to me) was responding poorly to my unexplained pushiness.

It was an unseasonably warm November day for Chicago. Although anal was off the table, I texted him to say we should take advantage of the nice weather and fuck on the roof because it was probably our last opportunity before Spring. We put our anal argument on pause to talk more about it later and agreed to finally have the roof sex we’ve been talking about since day one.

When he came up, I grabbed a condom and we went straight up to the roof. I locked the roof door behind us, a cautionary measure taken to buy us a little time if someone tried to come up. After some brief making out, he told me to turn around, lift my dress, drop my panties, and bend over on the edge of the roof. I complied. He kissed my inner thighs and made his way to my pussy with his tongue, teasing me, getting me worked up, just barely tasting me.

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Right when I thought he’d lick my clit, he stood up, dropped his pants, and put the condom on. He started out slowly inserting his dick little by little, making me want to push my hips back into his. With every thrust he went a little deeper and a little quicker until he was fucking me at that perfect pace. As he fucked me, I looked over the ledge, my heart racing, partially because a slight fear of heights, partially because the adrenaline rushing thinking about how anyone could look up from the street and see me bent over the ledge.

After a few minutes of this rush, he pulled out, laid on the roof and told me to ride him. I listened, straddled him, and rode his cock. He finished, I didn’t. I kissed him softly, then stood up and put my panties back on. He took the condom off and put on his pants. As we walked back inside and headed down the back stairs, he tied up the condom, and shoved it in a pocket of the drooping ceiling. I didn’t realize this until we got back to my room and he told me.

Once back in my room, after he divulged the condom ceiling information and I scolded him, I told him a little more about Roid Douche, I didn’t go into detail, but gave him enough to help him understand why I was upset about our earlier anal discussion. He told me he understood and wants me to be comfortable and wants to make sure it’s something I enjoy.

I want to trust him. I want to be able to get over this fear I have. I want to let go of the past. I want to move on.

Yours Truly,
Kallie Pygus

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.