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

Birthday Sex Marathon: Day 1

Birthday sex… probably some of my favorite sex. When it’s your birthday, your sex partners are pretty much obligated to make sure your birthday sex is everything you want and more. And while it’s your birthday, why not try to stretch it out as many days as you can? So I had myself a bit of a birthday sex marathon last year. To help my case in stretching out my birthday sex to a full 5 day marathon, I used my freshly healed piercings as leverage; after about 10 weeks my triangle piercing was healed, plus the vertical clitoral hood was also healed after 2 weeks. I timed the healing of my piercings perfectly so I could get all the birthday sex and oral I wanted.

Tuesday, December 6, 2016

Hardly a week since The Australian has left the country and he was still keeping his word. We messaged every day from the time he woke up to the time I went to bed. It was really sweet, most mornings I would wake up to a few snaps and a voice message from him. He really knew how to win a girl over, even from the opposite side of the country. As my birthday week approached, I warned him that I was going to be swamped with birthday plans pretty much every night so my attention to him would be cut short. Just before going out on Tuesday, I sent him a selfie on snapchat reading, “Day 1 of my birthday marathon…” Then went off to my plans.

The Chef and I met up for drinks. We made out, played a few rounds of pool, made out some more. As we finished up our last game, we sat and had another drink, a couple came up and asked if we were still playing. We told them no and the table was all theirs. We got back to our drinks and made out some here and there. The couple kept making eyes at us. We laughed, then headed out.

As we left the bar, he turned to me, pinned me against the wall and kissed me some more. When he pulled back from the kiss, he told me, “That couple totally wanted us.”

I laughed, “Oh totally… too bad they weren’t my type.”

We made our way to get some food. Cheap burgers at Red Hot Ranch. I went on a rant about how I much prefer a good time and cheap food over a fancy stuck up restaurant any day (although good food at a fancy restaurant is fucking delicious, just not my thing for a first date, second date, third date… more like a special occasion type of date). He made note.

After cheap food, we made our way to a dive bar and got another round of drinks. We sat at a dark booth towards the back of the bar. We chatted some, made out some more. After about 30 minutes of being there, it was announced that it just so happened to be a stand up comedy night that night.

Ever single comedian that got on the stage made some sort of comment about “What a cute couple,” or “Look at them, they are going to have the cutest babies,” or the one that didn’t beat around the bush, “Let’s just clear things up here, his chocolate skin against her milky white is what we need to see more of in this country.” So being an interracial couple in a bar during stand-up equals being the center of attention even though we went to the furthest darkest booth in the bar… you’re welcome for the material I guess?

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After the stand-up, we went back to my place and straight to my bedroom. All that making out throughout the evening had me soaking wet. We stripped down pretty quick. He knew my piercings were healed and so he went straight for the kill, mouth kissed down my body and down to taste my wetness.

He licked my clit as he slid his fingers in and out. This was the first time I was able to have oral in about 10 weeks and something was falling short. He did just fine, but I found myself bored. I kept trying to tell him to try a few different things, and tried to raise and lower my hips, but nothing was working all that well, then my triangle piercing started to hurt. I took that as a sign to just call quits on oral and pulled him up. I had high hopes for him based on his kissing skills, but was kind of disappointed.

As I pulled him up, he insisted on going back down, but I told him my piercing was sore, so probably best not to eat me anymore. I was tempted to just tell him he was only sub-par, but I was also hoping that maybe it was just my piercing and that hopefully the next time would be better.

We got back to kissing. Oh my god… so much better than the oral. How can he kiss so fucking good, but have me bored when he’s eating me? It was a complete mystery to me. As the kissing got more heated, he was rock hard, I gave him a condom to put on, then I slipped him into my soaking wet pussy. His throbbing, thick, large cock filled me up as he slid in.

As he slid in and out, his body pushed into mine and the piercings tickled my clit. It felt pretty fucking amazing, that is, until he slipped out when we were changing positions and his dick hit my triangle piercing.

“Fuck!!!” I cried in pain.

The night was over. I wasn’t going to cum anymore and I wasn’t feeling it enough to keep trying. He laid in my bed for a little bit, I got up and cleaned my piercings. As I got back to the bed, I kissed him a little, then told him I had to be up early (aka get the fuck out).

He got the hint, got dressed, and went home. I took a shower and then snapped The Australian a sexy pic, “home from day 1 of my birthday marathon.” He responded with several heart eye emojis, we chatted some more until I drifted off to sleep.

It felt weird, having this ongoing messaging with a guy all the way on the opposite side of the world as I filled my nights fucking other dudes, but then again, why would I commit myself to someone that far away when I’ve hardly spent two days physically with him? I can hardly commit myself to someone I see regularly, I’m not going to treat The Australian any different.

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.

 

When Two Bloggers Meet

As promised, a post to fill you in on the Turning Fantasy into Reality encounter with J. Reed, the blogger behind The Devil’s Hornet.

Today I met Jermaine (aka J Reed) at a Starbucks in South Shore. I arrived, I didn’t see him, so I ordered a green tea latte for while I waited. Soon after I ordered, he texted asking if I was there, I told him I had just placed my order. The barista handed me my drink, I took it to an empty table near the entrance and responded to some messages and waited. A few minutes passed and he messaged saying there was no parking. I continued to wait.

When he arrived, we introduced ourselves and then got talking about our blogs and how we got into writing them and what drives them. I told him how a friend of mine suggested I write The Boys I Encounter just based on my nature to talk about sex basically 24/7. I told him about an idea I have to take my blog national and fuck my way through the US on a 2-3 month road trip.

About 15/20 minutes into our conversation, he seemed nervous, yet eager to leave the Starbucks and even asked if I was ready to leave. I told him to slow down, we have plenty of time and I have yet to finish my drink. To take his mind off of the fantasy he has painted of us, I pushed the conversation a bit away from that and started to ask him more about his writing and his published works and talked about creative pursuits and trailed into movies and Nicolas Cage and Will Ferrel. I think this part of the conversation was the most genuine moment we had. Something about his eager demeanor and nervousness made the whole interaction a bit awkward for me. I feed off of the energy of those around me, he didn’t seem confident or comfortable, so it rubbed off on me some and I became more reserved.

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I paused, sipped my drink, and looked at him. At that moment, I was contemplating whether or not to go further with him. I could tell he really wanted to take me back to his place as he kept pressing about the fantasy we have built, but I wasn’t necessarily feeling any natural sexual connection between the two of us. I took a moment to step away and go to the bathroom and collect my thoughts. When I returned, we talked a bit more, I finished my drink, and then thought, “Fuck it, let’s do this.” I wanted to see if his skills in bed could match his writing. I asked for his address and we got in our separate cars and met out front his place.

When we got to his apartment, I instantly noticed how vacant it felt. Not much furniture or belongings. It didn’t feel lived in. There was a table in the living room, no couch or seating. His bedroom was basically just a bed and a desk. I took my coat off, set my purse down, and excused myself to go to the restroom again. Maybe a venti green tea latte was a bit much to drink before fucking, but I needed the caffeine as I didn’t get much sleep the night before and I woke up at 6am this morning. By the bathroom there was a girl’s pink scooter. He must have a daughter, I didn’t pry.

Once I got back to the bedroom, I took off my boots and my sweater leaving me in my jeans and tank top. He was standing by the bed, anxiously awaiting to fuck. I walked to him, we kissed for a moment. His full lips kissing mine were good, I love nice full lips as it allows for the perfect blend of suction and tongue. He seemed a bit reserved with the kissing, but that was fine. As we kissed, he unclipped my bra under my shirt, I then lifted my tank and bra up and over my head.

Now topless, he pushed me onto the bed, kissing me, then kissing down my neck, to my nipples. He quickly moved his lips from my nipples to removing my jeans. He admired my body, I pulled him in for a kiss, unbuttoned his shirt slightly and told him to take it off, he stripped completely naked. He then went into kissing my inner thighs. The use of suction was a bit distracting, he kissed and sucked on my inner thighs in almost a lip-smacking suction cup type of way. I prefer a bit of a softer touch, I crave being teased and denied. I need there to be a build up from soft to hard. Although the general idea of teasing was there, it seemed a bit forced and rushed. He didn’t seem at ease at all with what he was doing.

Soon enough, he took my clit in his mouth and licked and sucked away. All this subpar teasing panned out, as his eating skills were definitely there. As he ate me, he rested his hands on my breasts, but just left them stagnant. There was all this tongue action and nothing much more going on, not even any nipple rubbing or body massaging or fingering. Nothing. I guided one of his hands down to finger my vagina and then told him to pinch my nipple with his other hand.

He obeyed. Inserted his fingers and pinched me. Both were a bit off. I told him to pinch me harder, it got better. His fingers were a bit mismatched from his tongue, a bit too hard and fast. I told him to slow down. Much better. Everything started to fall in place, I even got close to cumming, but as I told him to keep going and how good it was feeling, he started to pick up the pace and pressure again throwing me off and taking me out of my orgasm.

His phone was vibrating for a couple minutes at this point. At first I thought it was a phone call and ignored it because I was close to cumming, but then when the orgasm disappeared, I pulled him up for a second, kissed him, and we both realized it was still vibrating. He got up to turn it off, an alarm probably.

He dived right back head first into my pussy, trying to pick up where he left. I tried to get back into it, I let him eat me for a few more minutes, but the moment passed. I wasn’t feeling it anymore. I sat up and kissed him again. He asked if I came. I then told him, “If I came, you would know, you wouldn’t have to ask.” I then continued to explain, “You did really good, you just need to spend more time building it up.”

He was about to go back to eating me, I stopped him and asked if he had a condom. He got up and grabbed one from his jean pocket, and sat back on the bed and told me to get him hard again; every guys way to ask for some pre-sex head, which I wasn’t going to deny him any. I took my sweet time. Kissing him for a bit, working my way down his neck to his nipples gently. I continued to rub his nipples with my fingers and trailed my kisses and tongue down each side of his torso to his pelvis teasing all his pubic bone and his thighs hardly grazing his cock with my lips. As the tease continued, he shook with excitement.

I sat up, smiled and started to lift my hair into a ponytail, he tried to reach up to touch my breasts, I leaned back barely out of reach, I then stated, “That is how you tease someone. It’s about getting that full body reaction before even really getting started.” I then went back to teasing a bit more, and worked my way to licking his shaft slightly and sucking just the tip of his cock, still building up the suspense. As his body quivered, I began to take his throbbing dick in my mouth slowly deeper and deeper, one hand rubbing his nipples and as my mouth came up his shaft I added my other hand below my lips, moving them in unison.

He moaned and shook with excitement. Within minutes of blowing him, he stopped me and declared, “I don’t want to cum just yet.” He then grabbed the condom and unwrapped it. He fumbled a bit, “It’s been a while since I’ve used one of these.”

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I’m not sure if that means he hasn’t fucked anyone in a while, or that he just doesn’t usually use condoms. I let that slide and once he got the condom on, I mounted him, riding his cock, kissing his lips and neck for a brief moment. I then sat upright, pushed my hands against his chest as I swayed my hips side to side and lift myself up and down on his cock. He stopped me again just before he was about to cum.

I unmounted and he directed me to get on my hands and knees. I listened and he entered me from behind, spanking me some, but it felt as though he was hesitating a bit. He fucked me fine. A basic move, but there was no excitement. He didn’t pull my hair, or rub my clit or push me hard into the sheets. Although he has read my blog and has some knowledge of what I enjoy, he didn’t push any boundaries. Once again, I feed off energy and that goes for the bedroom. He didn’t go for kink, so I allowed it to stay vanilla. As he continued to fuck me doggy style, I reached down and played with his balls some, and then with my clit.

I wasn’t feeling it, so I stopped him and turned to face him, now fucking missionary, we kissed and I lifted my hips into his as he thrusted into me. Not much of this and he pulled out, shaking, on the verge of cumming. This was my queue to get up and go pee. I went to the restroom, did my post sex piss, and walked back into the room. He eyed me up and down. I walked to the bed, looked at him, didn’t say anything yet, grabbed my water from the bedside, took a sip and walked to the desk to check my phone. It was 3:30, I considered giving him a little more time, but I was so over it, and kind of hungry, so I walked to the bed, kissed him and told him I was going to head out to grab some lunch before heading to work.

He seemed a little disappointed, but also as if he saw that coming. As we both got dressed, he told me he’d like to spend a day learning more about teasing and denial as most of the time he skips all of that and jumps straight to sex. I told him that could happen, I’d be down to see his skills when I’m properly worked up. He walked me to my car, kissed me goodbye, and I drove off.

I wanted so bad to unleash my kink, but at the same time, it didn’t seem quite right with him. The encounter was so spelt out from our emails it felt a bit contrived. Maybe if I give him the opportunity to tease and deny me and eat me for a day and learn my body, the sex could be amazing, but for today, it was just a fun experiment.

Yours Truly,
Kallie Pygus

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

 

Note to Self: Quit Bad Sex

Jay… Jay was a boy from Tinder. We matched back in July during my short stint back on the app. We had some good flirty banter on the app, he asked for my number, and we continued to text. He begged to meet me for a few weeks and when I finally agreed, he failed. The first time he tried to arrange to meet up with me, he claimed work was running late asking to meet at 11pm instead of 8pm so I canceled because I had to be up early the next day. The next time he tried to hang out, it was pouring out, so he then asked for a rain check, I agreed. Third time, supposedly a friend of his got in a car accident… Maybe it was true, but hard to tell when this is his third cancelation. I let it slide.

The day after his third cancelation, we finally met up. We went to a beercade and played some old school games. Beercades are my go-to for meeting guys if they fail at making plans. It means I get to play games instead of dragging out all the first date interview questions over drinks. It was fine. He was cute, confident, but a bit short and thin for my liking.

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After the beercade, we took a walk. We talked some more and he stopped me mid sentence, turned, pulled me in and kissed me and said, “I’ve been wanting to do that all night.” He is that guy that will say all the things he thinks you want to hear so he can fuck you. I knew that’s what he was trying to do, it was pretty obvious just by the texts before even meeting him. It was a good kiss; it even turned me on a bit. Overall, his charm was turning me on, but I could tell he would only be a one night fuck and nothing more.

On our walk, we went to another bar for one more drink… at least that was the plan. The bar we ended up at was doing karaoke night. I’m not one for karaoke. I hate feeling like I’m being put on the spot, especially unprepared. Jay demanded we both do a song. I reluctantly agreed. He ended up doing a Backstreet Boys song, I did The Joker by Steve Miller Band. He did fine, I failed. It was fun seeing him up there, but I was miserable doing it even though he tried to be a good audience by being up front and center singing along with me.

Once we finished singing, we went back to our booth. I was relieved that part of the night was over. We laughed a bit and made fun of each other’s performances. There was a break in our laugher, Jay went in to kiss me and we began making out. A song or two went by and our kissing got heavier and he got more and more touchy. This was the moment to either end the night or go somewhere to fuck.

After some flirty discussion between the two of us arguing who’s place to go to, we agreed to go to mine being that it was closer. When we got to my place, we went to my bar. I made us each a drink, then we took them up to the roof. Hardly a sip in, we were back at it, making out. As he moved from my lips to my neck to kissing my cleavage, I let out a coy giggle and told him to slow down or at least let me finish my drink.

He stopped, and took a sip of his drink. He then asked me what turns me on. I got to the point and told him all my kinks; ropes, cuffs, restraints, biting, hair pulling, nipple torture, tease and denial… His jaw dropped. He insisted he could be everything I wanted in bed. He told me he would tie me up and eat me and fuck me hard. I let out a slight giggle, thinking to myself that he thinks he can, but I knew already that he wouldn’t be able to deliver what I want. It’s not too hard to tell what a guy is like in bed based off of what he says and the way he carries himself. I could tell Jay was all talk from the start, the guy that thinks he’s all that but probably can’t hold up to the game he talks.

Alas, although I was aware of what he was trying to do, I was bored and horny. If he thinks he can tie me up and eat me the way I want to be eaten, let the games begin. We finished our drinks and made it back down from the roof and to my bedroom. When we got to my room, we started off slow, making out on the edge of my bed. He’s a fine kisser. Nothing spectacular, but not sloppy. He got a little handsy, but it seemed as if he didn’t know what to do with his hands, just put them in places. His lack of dominance showed, so I took control. I got up, pushed him back on the bed, and then straddled him.

As things heated up, I took off his shirt, then took off my dress. I kissed down his neck, to his nipples, down his abs, and teased him just above his pants. I then got up, leaving him rock hard on my bed. I grabbed my rope, threw it at him, and told him to tie me up and eat me and fuck me hard like he said he would. He grabbed the rope, looked at me, looked at the rope, and seemed unsure of what to do.

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I then directed him a little. To make it easy, I told him to just tie my hands together and then secure the rope to the bed frame. He took the direction, but stumbled the whole way. It was pretty obvious he never tied anyone up. After a few minutes of trying to figure out how to tie me up successfully, he finally got it. He then went straight into eating me. It’s hot when a guy eats me, yes, but part of the fun of being tied up is the tease and denial and losing that control of what’s to come.

As he ate me, he did alright with his tongue, but was very light with it. He had poor technique with his fingers. Like he would put them in and just keep them in one place instead of doing any type of come hither motion or swirling or even in and out. So basically he was a weak tongue with two dead fingers. Not good. I spoke up like I do and told him to use more pressure with his tongue and I thrusted my hips to help him understand the motion I need with his fingers. He kind of picked up on it, and was doing better for a minute, but then slowly drifted back to his light tongue and motionless fingers.

I got bored of his oral skills. The knots he tied weren’t all that tight, so I squirmed my hands out of the rope and took control yet again. I grabbed a condom, put it on his dick, and rode him. It only took the length of a song to finish. He came. I didn’t. I would usually keep things going either orally or getting him worked up again to fuck, but at this point, it wasn’t worth it. There was no way in hell Jay could get me off.

We both fell asleep and in the morning, when my alarm went off, I showered and left him in my bed. Once I got back to my room, he was sitting there already fully clothed. I walked him to the door, he told me he had a good time, I giggled and let him out. He tried to get ahold of me a few times since, but I just ignored him.

I don’t know why I put myself in these situations. I go on dates with guys and even once I already know that shit can’t go anywhere and that the guy isn’t going to deliver, I keep going along with it. I want to give them the benefit of the doubt or something. I want to see if they can fuck me well even if it’s just for one night. But it’s those guys, the guys that I know I will only fuck once before even fucking them, that end up being a waste of sex. I need to be better about turning down guys earlier in the night.

Note to self: quit bad sex, go home and take out my vibe; it always does a better job anyways.

Yours Truly,
Kallie Pygus