Birthday Sex Marathon: Days 4 & 5

Friday, December 9, 2016-Saturday, December 10, 2016

Happy birthday to me!

I woke up to texts, Facebook posts, messages, and calls from various friends and family to wish me a happy birthday. I also got a text from The Chef, a voice message from The Australian, and then a message from Neighbor Boy

Neighbor Boy and I hashed out how insensitive he was the night before.
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I don’t remember the comment that he made the night before? But regardless, he obviously wasn’t making shit better by telling me that my emotional breakdown was weirder than his comment.

After hashing it out, we made plans for that evening. His roommate’s birthday is a few days before mine, so his birthday party happened to be that night, which worked well for me. Double the party, one that night with roommates and neighbors plus their friends, then the next night was me and my friends. With this, I told Neighbor Boy I’d be home at 9pm and we could fuck before the party started at 10pm.

When I got home, I messaged him. He was failing….

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I was getting frustrated and he wasn’t delivering birthday sex as promised. Shortly after “That’s not my fault” he walked into my room. It was on.

We made out. I was still naked from my shower. He undressed quickly, continued to kiss me, then kissed down my body. There wasn’t much time till the party, so we kept it quick. As we finished, I told him he still owes me more birthday sex. He got dressed and headed down. I told him I’d be down shortly. After he left my room, I got dressed, took a selfie on snapchat to send The Australian my “Birthday Marathon day 4…” snap.

Once I was done getting ready, I made my way down to the party with a few of my roommates. I received hugs and happy birthdays from neighbors and friends as I arrived. Soon enough, drinks were poured, bowls were smoked, and games were played. Neighbor Boy and I hung out at the party as if we didn’t just fuck, and all went on.

That’s the thing about fuck buddies; there’s fucking when you’re behind closed doors, then there’s the way you interact in the real world. Neighbor Boy and I had a way of talking shit to each other when out of the bedroom. He’d say some sarcastic ass remark to me, and I would dish it back. The only way it was made known that we probably fucked is he’d walk by and grab my ass while we played pool. Other than that, there was no kissing, no physical contact, no real flirtation.

As the night progressed, I was getting a bit tipsy and my phone kept buzzing. It was The Australian. He was sending snap after snap and even a few messages on WhatsApp. I caved and started to message back and sent him some snaps. Had I been sober, I would have refrained. But the alcohol got the best of me and I enjoyed talking to him.

This caught Neighbor Boy’s attention. He came over to me and told me to put my phone away. I told him it’s my birthday and I could do whatever the fuck I wanted. He then insisted we played pool. I was just the right level of drunk to kick his ass. My claim for pool is that I have to be drunk. Too sober or too wasted I fail, but slightly drunk, I’m wonderful. As I kicked his ass, my brother texted that he was there and to meet him out front.

My brother and his friend came in and went straight to the pool table. I introduced him to Neighbor Boy. Shit was a little awkward, but the night went on. The four of us played doubles. Several rounds later it was nearing 4am. I was exhausted. I knew Neighbor Boy was drained. The party was dying. It was the four of us and maybe a few other people. My brother kept insisting another round. I finally had to tell him I was about to go up to my room and pass out. They left. Finally.

I went upstairs, Neighbor Boy stayed behind but said he’d meet me upstairs once he finished his cigarette and brushed his teeth. I messaged him when I got to my bed to tell him I was passing out but my door would be left unlocked. He came up and we fell asleep.

I woke up to Neighbor Boy pushing his morning wood against my ass. I rolled over and we got straight to business. It was fine, but I stopped him not long after we started. My triangle piercing was killing me. I couldn’t keep fucking, it was unbearable.

He left frustrated. I brushed it off and went on with my day. He messaged me later…

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My birthday marathon came to a wrap. I came a handful of times. Got tied up. Played with toys. All the oral sex. Semi-successful anal sex. Had an emotional breakdown. The actual birthday sex quicky. Morning after birthday piercing pain. There were ups and downs, but I was satisfied overall.

Yours Truly,
Kallie Pygus

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

3 Boys, 24 Hours

The Australian left at around 4am. I woke up at about 11:45am to a “good morning” text from him. He hasn’t left yet, but he was already keeping his promise to stay in touch and we continued to text until his 6pm flight. I also woke up to a “hey” text from Neighbor Boy. He hasn’t seen me since before my recent VCH piercing and wanted to know if I was free that evening, I told him I had a date with The Chef at 8pm.

I wasn’t free that night, but there was a window of time free from the moment Neighbor Boy would be getting home from work and when I would need to be leaving for my date. And that is when pre-date quickies was born. He told me he’d be up around 6:30pm to fuck.

Late as per usual, Neighbor Boy came up just before 7pm. I blew him briefly and we fucked. After our quickie, I got dressed and ready for my date with The Chef, no time to shower (so gross, but fuck it). I ordered a Lyft, realized I was running late, texted The Chef and made my way to Balena.

As I arrived, I felt out of place. It was upscale and the people dining there were all a decade or more older than me. It was the type of nice restaurant my family would go to for a special occasion, not quite what I’d expect of a first date with a guy my friend matched with on Tinder, but then again, he’s a chef so good food obviously matters.

Blunt as always, I laid it out as soon as I sat down and told him that the place was a bit overboard for a first date. He told me we could go somewhere else, and I told him it was fine, I’m sure the food is fucking amazing, so might as well stay. And it was; everything we ordered was made to perfection.

When the bill came, he went to pay in full, but I always offer to pay half, he went with it. I’m iffy about situations like this; I don’t mind paying half, and I usually insist on it, but being that he’s the one that chose a place that ended up coming out to nearly $150 check for the two of us seems a bit steep for a first date, but whatever.

Overall, throughout dinner, we made a lot of connections and the conversation was fluid, he was nice, but there was no spark. I honestly got more of a gay vibe from him than anything, but he even made a point to say he’s not into dudes even though I never mentioned it… meaning he’s aware he comes off as gay?

Outside Balena, I ordered my Lyft home, we chatted some, said our goodbyes, it was kind of awkward. The Lyft pulled up, he went to hug me, then I went ahead and kissed him? Why the fuck did I kiss him? But the kiss was actually pretty fucking hot. His full lips lightly sucking mine and the perfect amount of tongue made for a really good first kiss. It was on, I told him to get in the Lyft with me.

I wasn’t really into him as a person, but that kiss had me intrigued enough. We got back to my place, I showed him around, told him to sit while I excused myself to pee. I went to the bathroom and checked my phone, The Australian texted saying he was in LA with a few hour layover till his connecting flight to Australia. I texted him back, “I’m still out with my gay hubby, sorry! Have a safe flight home. I wish you were here!” I then peed, washed my hands and went back out to The Chef.

I took him to my bedroom and we made out some more. We broke for a quick pause as I blurted out, “Sorry, just a quick FYI, I got my vertical clitoral hood pierced like a week ago and my triangle several weeks ago, they’re still healing. Technically I can have sex, but I also kind of made a rule not to have sex with new guys while they’re healing.” He said that’s fine and we proceeded to make out.

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As the kissing got more and more heated, he told me he gives great massages. I can’t resist a good massage even if it is his excuse to get me basically naked. I stripped down to just my panties, gave him a bottle of lotion, and let him work his magic. He massaged my neck, back, arms, legs, and teased me by gently rubbing my ass and inner thighs barely grazing my clit.

I couldn’t take it anymore, I turned around and pulled him in and kissed him. He kissed down my neck and to my nipples. Fuck! I’m totally screwed. He got me beyond soaking wet. I resisted, pulled back, sat up, and looked at him smirking. I know what he’s doing, but I needed to resist a little longer before I could cave.

He then asked if I have ever been with a black guy. Thinking to myself, yes, many and one just a few hours ago, but I told him, “Yes, why is that every black guy’s question?”

He then explained how huge he is and wanted to warn me before moving forward. I laughed and told him, “I’ll be just fine, but thanks for the warning.” I then proceeded to tell him, “I might need to break my rule, definitely no oral and no touching the piercings, and you’ll have to be extra gentle…” Fuck it, breaking my no sex with new people while my piercings are healing rule. This guy doesn’t have minimal repeat potential, might as well get it in now.

He agreed to being gentle and we went forward. He stripped down and revealed his big black cock. It was definitely pretty fucking huge, but not the largest I’ve been with and I told him as I saw it, “You weren’t lying, you are pretty fucking huge… but I’m sure I can handle it, I’ve been with bigger.”

A shot to his ego, but someone needed to do it. He was cocky and that shit doesn’t fly with me, plus I was only telling him the truth. I got up and grabbed him a condom. We kissed a little longer, he slipped the condom on, and then made his way into my soaking wet pussy. His cock filled me up as he slowly pushed in and out of me.

Yes, his cock was big, but I’m no size queen. What really had me going during the sex was the continuous making out. He was definitely high in the ranking for his kissing style. We fucked missionary for a few minutes before I stopped him, my triangle piercing was hurting and I couldn’t risk fucking up my piercing over sex. I really wanted to keep going. If it wasn’t for my healing piercings, I probably would have cum, a rare first fuck orgasm.

After sex, he lingered, but I was kind of over it. I told him I should probably get some sleep. He got the hint, got dressed and headed out, it was about 2am.

In less than 24 hours, I blew and/or fucked 3 guys; oops (sorry, not sorry)!

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

The Magical Third

So this happened today… Neighbor Boy and I have been talking about finding a third (male or female) or a couple to add to our fun. We literally just joined Feeld today, but hours before I even got our profile up and running, I got a random message from some guy I don’t know on kik.

Only a few messages later, I found out he lives in Chicago, he’s bi, and some of his kinks so I couldn’t resist to ask if he’d be down for a threesome with Neighbor Boy and I.

And just like that, I magically found a third. Not only that, but I might have some fun on the side with Kik Boy. We will see what happens when I meet him. And of course, I will fill you in on all the dirty details.

Something about me screams sex apparently because I have sex falling from the sky.

Yours Truly,
Kallie Pygus

Exclusive Fuck Buddies?

Not long after Neighbor Boy fulfilled his duties for the first night of The Convenient Oral Agreement, he pushed negotiations on condom use, cum shots, and opened discussions for being exclusive fuck buddies…. Never have I ever heard any situation where fuck buddies are exclusive. Is this even possible?

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Before you even ask, the answer is no, I don’t allow him to fuck me without a condom. That would be stupid. We are both fucking other people and in no way have become “exclusive fuck buddies.” But that being said, this conversation, along with a few similar conversations we have had since, got me thinking about terms of casual relationships.

Facials… really boys? And why do guys always push to fuck without condoms? Is it possible to fuck someone exclusively without being in a relationship? Or can fuck buddies be a “priority” for condomless sex? If two people agreed to be “exclusive fuck buddies,” how is that different from being in a monogamous relationship?

What the fuck is an exclusive fuck buddy?

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

 

Location, location, location

A couple days of messaging after my first sexual encounter with Neighbor Boy, we flirted a bunch and then the convenience has been revealed. It’s as easy as saying “I want to fuck” and within minutes Neighbor Boy could be in my room. As for our first time fucking, he initiated by telling me he wants to fuck me when he gets home. Easy as that…. but because I have a uterus, my period decided to interfere.

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He seemed unsure. Like he said period sex was fine, but also hesitant. Then the way he approached telling me that he wanted to fuck and what he wanted to do; at the moment it was a turn off. It also threw me off guard that he was literally negotiating what we were going to do in bed that evening. It was different, and he still does it from time to time, but I’ve learned to enjoy it and it even becomes more like foreplay. A combination of discussing sex to come and sexting.

Lucky for him, my late period didn’t actually start like I thought it did. It was more of pre period spotting that went away shortly after I messaged him that, so he dodged having period sex the first time he fucked me.

The sex was hot. Although he was hesitant because I thought I was getting my period, he still ate me some, played with my vibe, and put in a good amount of effort trying to get me off. I didn’t cum, I rarely cum the first go, but it kept me intrigued and wanting more.

Our boundaries were still a bit blurred. We agreed to have a fuck buddy/friends with benefits situation. I like kissing still, he doesn’t because it’s “too intimate.” Although kissing is too intimate, he likes cuddling? That confuses the fuck out of me. That first night we fucked, he spent the night and cuddled me. It was nice, but weird at the same time.

Every relationship is different. I’ve casually dated and had fuck boys before, some boys like to kiss and cuddle, others don’t. Some like sleep overs, some don’t. I personally like all of the above (sleeping has limits though, snoring and anything that may prevent me from sleeping will send me packing).

This arrangement is unique. I thought having a fuck buddy one floor beneath me would be complicated and messy, I was wrong. It has been very hot and just thinking about the endless possibilities is a huge turn on. It’s easy enough to call him up whenever I want. We even have a convenient oral sex agreement (more on this later). He has his rules, I have mine. We both comply and push boundaries and learn about one another’s sexual desires.

If we want a quickie, there’s no need for dialogue or drinks or hanging out, we can text and within moments we can be fucking, finish, and go on to our separate apartments. If we want a sleep over, it can happen (snoring permitted). And when he does start snoring, I can kick him out if he’s at my place or just up and leave if I’m at his. One flight of stairs, the shortest commute ever. It really has been the most convenient sexual arrangement I’ve had (minus living with my ex boyfriend).

What makes an ideal fuck buddy?  Location, location, location. This was the start of a good arrangement with the downstairs Neighbor Boy and I was very excited for more to come with him.

Yours Truly,
Kallie Pygus

 

Proceeding with Caution

The morning after my encounter with Drunk Neighbor Boy, I woke up early to drive up to the campsite to meet up with my family. Shortly after I got there, he messaged me to apologize for his drunkness and to thank me for coming to his birthday party. Our banter was on point. He asked if he made an ass of himself, I poked fun at all of his ramblings of me being attractive.

It didn’t take too long for him to ask me out. I agreed. He then tried to see if we could hang out that day. I told him I was out of town for the next few days and would be back Tuesday. Without even asking, he then declared that Wednesday we would hang out. Lucky for him I was free.

Wednesday rolled around. No word from him since the morning after his party when I agreed to hang out with him. Now it was getting close to 6:30pm and I haven’t heard from him. I should have just canceled on him, made him think twice before being inconsiderate and not confirming or actually coming up a plan. Alas, I was intrigued by the fact that he lived downstairs and those possibilities, so I messaged him:

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His mention of telling me to wear shorts or tight jeans was a red flag. Who the fuck thinks it’s ok to tell a woman what to wear like that? I still give him shit to this day about it and he still tries to say it was a joke. In spite of his jeans comment, I wore a dress, and not a dress that was revealing. It was just above knee length, t-dress with a high neck line so absolutely no cleavage.

Anyways, after all this, I was starving, he was dragging ass, it was about 9pm by the time he was finally ready. My friend was still chilling, but she was about to head out, I told him to meet me out front in five because I was walking my friend to her car. He agreed. After walking her to her car and then walking back to the front door, I waited. He wasn’t there. I messaged him to hurry his ass up. A few minutes later he finally got his shit together and came out. I instantly gave him shit for his behavior, he apologized but insisted it was a joke.

We walked to DMK burger down the street. On our walk and during dinner we flirted, asked some basic questions to get to know each other, and discussed our expectations. I told him I wasn’t looking for a relationship, he agreed. We kind of hit it off now that we understood that we were both interested in casual sex, but I did tell him I would have to proceed with caution.

As we continued this conversation and walked back to our building, he asked more about what I mean with proceeding with caution. I explained to him that because he is my downstairs neighbor, obviously there are times we will run into each other with other people or if one of us catches feelings and the other doesn’t, things can get weird. He assured me that he would be totally fine and that if he saw me with some dude, he would smile at me and we would keep walking. He even threw in there that he would high five the dude or something which made me laugh.

We got back to our building, I invited him up to my floor for a drink. He accepted. We went directly to the bar and I made us each a whiskey ginger. We made our way up to the roof and kept chatting a bit more about our expectations. He explained his thought process, saying that it would be cool to have a fuck buddy that lives right upstairs. I agreed and it definitely felt like we were on the same page. We then started to discuss some of our sexual styles and kinks. We seemed to understand what the other wanted quite well.

He finished his drink and set it down. I took the last sip of mine, and that is when he went in to kiss me, drink cup still in my hand, I felt around to set my cup down, then wrapped my arms around him and kissed him more. The kiss was hot, not quite my style, but still enticing. He rubbed his hands down my back to my ass to grab it. Obviously an ass guy. He then went to lift my dress. I stopped him.

I kept telling him I’m proceeding with caution and I still can’t be sure if him being downstairs is too close to home. He kept insisting that it would work out just fine. I then joked and said, “You might not be any good.”

He laughed and then proceeded to tell me, “You might not be any good,” and then added, “I can show you and then you can show me your skills.”

I laughed, “Hmmmm, maybe…”

Neighbor boy pushed, “Let me eat you, even just for 60 seconds, to give you a taste of what I can do.”

I laughed, “Tempting. But I’m still being cautious.”

He persisted, “Just 60 seconds so I can show you and then you can show me.”

I bit my lip, thinking about how hot it would be, but also hesitant still, “I have yet to have oral or fuck on the roof…”

“So bend over and let me eat you.” He pressed.

“Fine.” I agreed, slid off my underwear, and looked at him, wanting him to give me direction.

“Turn around and bend over.” He asserted.

I listened and bent over, hands on the ledge. He came up behind me, kissed my neck, and bent me over further, my body now pressed on the ledge, he worked his way down and lifted my dress and ate me from behind for a few minutes. Something about being on the roof looking down at the sidewalk was both frightening and a huge turn on. At any moment, someone from the building could try to come up to smoke or someone could see us from across the street. I was getting into more than expected and his oral skills almost met the hype he gave himself.

He stopped, I turned around and kissed him and unzipped him as we made out, grabbing and teasing his dick. Once I got him all worked up, I worked my way down to kneel to blow him. I took him in and out of my mouth, looking up at him enjoying every bit of it. After a minute or two, I pulled away and stood back up.

“Why are you stopping?” He asked.

“You gave me some, and I gave you your 60 seconds and then some, now I’m done.” I explained.

“Don’t stop, let me eat you some more…”

“Ok, but not over the ledge.” I agreed, as much as it was hot, I also have a minor fear of heights.

He took off his shirt and laid it down on the surface of the roof  a bit further back from the front and told me to lay down. He began to eat me for a brief moment, then asked about 69. I agreed. He laid down, I kissed him, then worked my way down towards his cock and straddled his face. This lasted several minutes. It was hot, I was enjoying it, but I also knew at that moment there was no way I would cum from it. I was excited about the possibilities with Neighbor Boy, but wasn’t in a rush to test him out fully that night. I unmounted his face and continued to blow him a few minutes longer then stopped. I worked my way back up to his lips, gave him a kiss, and then stood up to grab my underwear from the front of the roof.

“Really?” He asked.

“I’m not gonna cum like this, I’ll probably go in and grab my vibe…”

“I like watching.” He tried.

I laughed, “There will be plenty more chances for that, but right now, I’m good. You gave me some and you got some.”

He pulled up his pants, zipped up, and put his shirt back on. We made our way back to my apartment. I walked him to the door, kissed him goodbye and went to my room to take my vibe out.

I wasn’t sure what to expect going into tonight, but I am glad he and I were upfront and discussed our expectations right away. This type of arrangements rarely work, even if the two people don’t live in the same building. I still wasn’t sure if it could work, but I was excited to see where things went. The next day he messaged me:

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The endless conversations we’ve had via messenger since this evening have been very open and honest. We’ve both inquired about our experiences, our likes and dislikes, inform if/when we’re sleeping with other people, and have discussions to make sure the other is satisfied with our sex. This is definitely different than most fuck buddies I’ve had, but I like it. It helps inform our sex and shapes our expectations of one another. It’s been good and proves how important communication is especially when sex is involved. More on communication and it’s imporatance another time.

Yours Truly,
Kallie Pygus