Hopefully…

About a week ago, I posted We’ll see…, which was prompted by a text conversation I had that day with Chase inviting him to a party that Friday. Friday night came, and I still haven’t heard from Chase to see if he was definitely coming or what time to expect him at. I had a gut feeling he wasn’t coming, but I texted to confirm at around 11pm. He responded a couple minutes later with the dreaded message that he wasn’t going to make it.

I was already mentally prepared for this, I had a feeling he’s been slipping. As much as I wanted to tell him to fuck off, I decided to keep calm, so I sent him a light text saying “For sure. Another time ;)” I then went on with my night, hung out with friends, and enjoyed the party without Chase.

Last night I was supposed to hang out with one of the Tinder boys at 9pm, but he texted saying he had to stay late at work and wouldn’t get out of work until 10:30pm instead of 8pm. I told him that would be too late, so we postponed. As soon as those plans fell through, I had an evening free. I should have done something productive, like clean my room or write a blog post, but instead I texted Chase.

He said he was at work until 8pm, then playing basketball, but maybe after. And there was that word again, “maybe.” He’s always a “maybe” or “we’ll see.” I told him to text me when he’s done playing basketball. At around 10pm, he texted asking if I was still free. I told him yes. A few minutes later, he texted that he was out front, meaning he was already on his was when he texted to see if I was free. He came up, I made us drinks, we chatted a bit… Everything seemed totally fine. That is, until we went to my bedroom.

We kissed a bit, but I could tell something was off. He is usually very sexual and rubbing all over me, but last night he was going through the motions and hardly doing anything. We stopped and I asked him what was up. He said he wasn’t feeling well. I asked if I could get him anything. Then he explained that he didn’t feel sick, but he had something on his mind. I tried to get him to tell me, but he said he didn’t want to talk about it.

I was getting frustrated because I haven’t seen him in almost two weeks and on the day we hang out, he’s being extra distant. Then because I was getting frustrated, he was getting frustrated. The whole thing escalated and he ended up leaving. We didn’t really fight, per say, but there was definitely tension and I called him out for being a dick.

I texted him not long after he left.

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“Hopefully.” That was all he had to say in response. I don’t think I will hear from Chase again. I don’t know that I want to. As great as he seemed at the start, he showed how much of a downer he can be over the past 2 months. One thing that stood out to me when we were talking, before we had the argument even, was that he claims that he has a habit of self sabotage. Just like he admitted to being aware that he is an asshole before (see Spiralled Emotions), he is also aware that he is self sabotaging. Both seem at least partially intentional and he could probably stop if he wasn’t stubborn. Chase is extremely intelligent, charming, and very handsome. I really do hope he can get past his front of being a self sabotaging asshole, even if it’s not in time for me.

Hopefully…

Yours Truly,
Kallie Pygus

The Tale of Pigeon Bitch

While in NYC about a month ago, I thought I would Tinder/OKC my way through and meet up with a few guys. Well, there were a lot of guys trying to get me to go out, but it never quite aligned for most of them, plus I ended up busier than expected and wanted to spend more time with my friend Ana, who I helped move there.

My profiles were simple. I reopened my old OKC account, updated the photos, deleted all the text, all the questions I answered in the past were still applied, so no need to reanswer questions. Then, I redownloaded Tinder and uploaded new photos. In both OKC and Tinder, I wrote “Chicago artist and curator visiting NYC for the first time. If you were to take me on a NYC date, where/what would it be?” I filled in OKC a little more, but kept it very simple.

I had floods of matches and messages. Most of the guys saw the fact that I was visiting and took it as an invite to just fuck me, so most openers were something along the lines of, “Come to my place and I will show you a side of NYC you wouldn’t see anywhere else.” Past all the DTF openers, there were quite a few guys who invited me to dinner, drinks, a picnic in Central Park, dancing, art museums, music, etc.

After all the conversations and people trying to tell me what they would do with me on a NYC date, I narrowed it down to one guy to meet from Tinder my friends and I now call Pigeon Bitch.  That’s right, Pigeon Bitch got his nickname because his opening line was “How do you feel about grooming and feeding the NYC pigeons?” That, plus he had a picture of him chasing pigeons and another photo of him with a pigeon shirt. All weird, but the conversation was hilarious and he seemed sweet. Not only did he have a sense of humor, but he’s muscular, dark, with a great smile.

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We did not go to groom and feed the pigeons. I know, I was disappointed too! He even took the pigeon joke a step further to invite me to a pigeon light show, which was actually a thing going on in Brooklyn that weekend, but none of the days/times worked. After a while of talking, he sent me several ideas to choose from. He was very adamant about making me love NYC because I told him my friend is trying to convince me to move there and he might need to help her with that. He took that as a challenge.

We agreed to see some Jazz in Manhattan and to meet up an hour before the show at a nearby bar at 8pm. My friend Ana and I had plans early that evening, so it worked out perfectly. Ana and I went to a bar and then grabbed some food with a friend of hers named James, then the three of us walked to the bar I was meeting up with Pigeon Bitch. We got to the bar just before 8pm, and were debating if we should all sit at the booth and have it be the four of us for a round, or if I should go sit up at the bar. Ana came up with a fucking fantastic idea, I was to sit at the bar and after Pigeon Bitch arrives, James and her would send us over drinks and be flirty and pretend to be swingers trying to fight for our attention. I laughed and agreed, so went to sit by the bar.

I sat at the bar, ordered a drink, and waited for Pigeon Bitch. He texted saying he was running late, but would be there by 8:10. He arrived ordered a drink, and then we did some basic introductions. I realized I didn’t do much questioning when we were just chatting. I didn’t know anything about him aside from the banter about pigeons. I learned he got his muscular build because he is a personal trainer, does crossfit competitively, and is the assistant tennis coach for an after school program. He’s lived in NYC his whole life minus when he went away to college for environmental science.

Once we finished our first round of drinks, I was expecting drinks to be sent over from Ana and James, but then Pigeon Bitch looked at the time and said we should start walking to the Jazz place. We closed up, and left. When we got to the Jazz place, I had 10 texts from Ana asking how the date was going and saying sorry because she didn’t get the drinks in on time for our prank. I told her it was ok and I would text her later.

The hostess took us to our seats, which were at this super tiny table at a half booth, I sat on the booth side and Pigeon Bitch had the seat across from me. He then decided even though there were people on either side of us, he would squeeze onto the booth side next to me to be closer. We ordered some food and a round of drinks, talked a bit more, and waited for the music to start.

As we sat there, I got another slew of texts from Ana. I knew she was worried about me because I was on a Tinder date in a city I’m not familiar with, so I opened the texts to see a gif of Colbert doing a vigorous finger banging motion with his hands. Being that we were in tight corridors, Pigeon Bitch saw it and we both laughed.

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This instantly changed the pace of things. We went from casually talking and just sitting next to one another, to Pigeon Bitch rubbing his hand on my knee and got a bit more touchy. I knew it was because of the gif he now thinks he has a good chance in getting laid (which I’m not gonna lie, I already was planning on fucking him). I thought it was funny how his body language drastically shifted once sex was on the table.

As the music started and the food was delivered, he continued the sexual tension by playing footsie with me until we were done eating. Once we finished, he put an arm around me and rubbed my leg with his other hand. The band came to a brief break, this was his opening to kiss me and he took it without hesitation. His full lips locked into mine, and he sucked on my upper lip as I took his lower. We then made out briefly, his technique is very comparable to my own. Some light tongue with a blend of lip suction. I’m not a fan of excessive tongue. Pigeon Bitch’s kisses were definitely enjoyable.

A few drinks later, the Jazz wrapped up. We decided the adventure wasn’t over, so we went to go play ping-pong, but the place he wanted to go to was closed. We then settled to go to a bar with a pool table back in Brooklyn. He guided us from one train to the next to get to our destination. On every train platform and on the ride there, we made out some and chatted, and made out some more. The night was still young and the sexual tension was heating up.

While on one of the train platforms, our discussion escalated. He began asking about what I like during sex. I was honest, explained that I like being submissive; I love being cuffed/tied up, teased, playing with toys, and nipple clamps (also nipple biting/pinching). His jaw dropped, he wasn’t expecting that. He then explained that he’s done some kinky stuff, but really only light choking and some smacking around, but he’s never tied anyone up or used toys. He then added that he was excited to have some fun with me because there are some things he always wanted to try.

All this talk about sex, I was almost willing to just skip playing pool and go back to his place, but at the same time, I still wanted to see more of New York. When we got off the subway, we walked a few blocks to get to the bar. He told me we were in his neighborhood. It was a quiet, tree-lined area, with rows of brownstones; very residential. I was impressed and asked how he could afford to live in such an area. And that is when he revealed he was living at home with his parents! Usually that’s a deal breaker, but he’s a one night fling, so does it really matter?

I made fun of him for living at home still. He then told me that he lives on the lower level and he has a separate entrance so it’s very private. He also added that the main reason he’s living at home is because he’s saving to buy a place. He’s 28 and would like to own a place in Brooklyn by the time he’s 30, so I guess that’s a little more acceptable. Right?

When we got to the bar, we walked straight to the back to see if the pool table was open. There were a few people playing and someone already had dibs. Pigeon Bitch went to ask the bartender for quarters, I intervened and pulled out quarters from my purse, went up to the pool table, and called next game. When the bartender finally got to Pigeon Bitch, because quarters were already resolved, he asked what I wanted to drink. I ordered a Jameson Mule. I’m now several drinks in and feeling a little tipsy, but when the drinks are free, keep them coming.

As the guys on the pool table finished their next two games, the table opened up and Pigeon Bitch and I took over. He racked, I broke. My break was fine, but my game was all down hill from there. We were playing calls, which I am usually pretty good with, but every shot I took ended up being a lucky slop so it kept going back to Pigeon Bitch. I had a few too many drinks for my game to be on point. It was a close game, I only had a ball or two left when he was down to the 8 ball. In the end, I won because he scratched on the 8 ball. Just my luck.

The Jameson was really kicking in. He asked if I wanted another drink, I declined. If I was going to fuck him, I needed to sober up a little, so I told him I was hungry and he should show me why NY pizza is supposedly better than Chicago pizza. He laughed and agreed. We called a Lyft and made our way to Artichoke for some slices. The pizza was decent, extra greasy, tasty, but couldn’t compare to Chicago style pizza. My tipsiness subsided to a good buzz. I was ready to bring the NY adventure off the streets and to his bedroom.

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We caught another Lyft and went to his place. On the way, I continued to poke fun at him for living with his parents, but he took it like a champ and brushed it off. When we got to his place, we went through the back and down through the lower garden stairs. His room was secluded, so I felt a little at ease. His room was fairly big, especially for New York. There was a queen bed, a couch, TV, desk, and large closet. All it was missing was a bathroom and kitchen and it could have been a decent studio apartment.

While he turned on some music, I sat on his bed waiting patiently. He sat next to me and went in to kiss me. It quickly escalated. The night had been filled with making out and discussing our kinks so the tension was ready to burst. It took mere seconds to go from kissing to being stripped down to nothing. He kissed all over my body and worked some magic with his fingers on my clit. We have been discussing our kinks all night, so it was pretty much all action by the time we were naked.

Once I was worked up from the clit finger tease, he got up and found some rope he had. He kind of hesitated, I told him to tie my hands above my head to the headboard. I think he secretly wanted to be tied up himself, he seemed a bit disappointed that the rope was for me, but he went with it. He tied me in such a way that the rope could still spin so I could be face up or face down, allowing a little more freedom in the positions while still be restrained.

He started off slow. Kissed me gently on the lips then down my neck while reaching a hand down to my clit. As his mouth approached my breasts, he circled my nipples with his tongue. I squirmed a bit, I pushed my hips up, thrusting towards his hand and cock. He then stopped me by pinning my legs with his knees on my thighs. His licking soon turned into sucking which quickly changed to biting my nipples.

Once he got me nice and wet, he reached to grab a condom from the bedside nightstand and put it on. He rubbed his tip on my clit and down to my vagina slightly sticking in just the tip, then sliding it back up to my clit. He did this several times as I lifted my hips up towards him. He eventually thrusted in hard and deep, held it there, kissed me, then with subtle circular thrusts he fucked me for a few minutes. He then flipped me over, had me bent over doggy style. While he fucked me, he rubbed my clit with one hand and spanked me with the other. It was fucking hot. He came. I didn’t, but I was extremely close. He told me he wasn’t done with me yet.

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I was still tied up. He took off the condom, went to the bathroom, and then came back to tend to my needs. He went straight into biting my nipples while playing with my clit. I rarely cum from a guys fingers, but something he was doing was working. I kept telling him not to stop, keep doing exactly what he’s doing. He listened and a couple minutes later I was enjoying a manually stimulated orgasm from a guy I just met several hours earlier. That was a very pleasant surprise.

He untied me and grabbed me some water. After I took a few sips, I went to kiss him and grabbed his dick. He was rock hard and ready to go again. I asked him what he wanted. He surprised me yet again; he told me to step on him. I’ve never stepped on a guy, but there’s always a first. I agreed. Before doing so, I asked what exactly he wanted, he explained to step on his chest, and lightly step on his neck, and rub my foot on his dick and balls without stepping on them. It was obvious he has done this before, he knew exactly what and how he wanted it, but it wasn’t something he brought up earlier in the night so it threw me off guard.

He had high ceilings, so it was easy enough to just stay on the bed. I stood on his chest, teased him a bit by rubbing my feet up and down his abs, then while one foot stayed on his chest, I placed the other foot on his neck and lightly pressed down choking him a little. While I did this, he stroked his cock with his hand. He was really into it, having a naked chick stand on him while he jerked off. He even asked if me stepping on him was punishment for him losing the pool game. I told him yes and that he’s been a bad boy. This got him more worked up. I then released his neck and ran that foot down his abs to intervene with his masturbation, rubbing my foot along his dick and balls as he asked, then lightly pressed his dick up against his pelvic bone. While standing on him, I started to lose my balance a little, so my foot that was playing with his cock needed to be grounded a bit to catch myself. During this small slip,  He pulled me down and jerked off for a few seconds until he came all over my tits.

He got up, grabbed us some wipes, we cleaned up, and fell asleep. He spooned me the whole night, which is always a nice feeling and even nicer when you get woken up to a throbbing cock pushing up against you while having your clit lightly rubbed. I always love being woken up to morning sex.

He grabbed a condom. I told him to sit on the couch. He listened. I was still in control from stepping on him the night before. He was way more submissive than I usually like, but I played along. I straddled him, not taking him in yet. I kissed him, then lightly bit his neck, kissed down his chest as I played with his dick. He quickly unwrapped the condom, and I grabbed in from him, sliding it down his cock, then played some more, teasing him a bit by running his tip across my lower lips. He kept trying to grab hold of his dick to get inside me, I kept pushing his hands away not allowing it. Once he stopped fighting it, I inserted just the tip and lightly took it in and out of me, then slowly took him in deeper and deeper gradually. Once I finally took him in to his base, I picked up the speed and fucked him. He came. I didn’t.

I got up, grabbed some water while he took off the condom and went to the bathroom. I laid on his bed, exhausted from only sleeping about four hours, I started to drift a little. He came back and laid next to me, kissed me gently and started to work his magic with his fingers. As good as it felt, I wasn’t going to cum, I was spent. I grabbed his hand to stop him and we laid there cuddling in silence for several minutes and drifted into a  nap.

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We woke up to his alarm about an hour later. He invited me to take a shower with him. Although he had a bathroom across the hall from his bedroom, the washer and dryer was also next to his room. He heard his mom doing laundry, so before I could walk out to take a shower with him, he told me to wait so he could check to see if she was there. I laughed, after a night of fucking, I was pulled back into reality. He was a 28-year-old guy living in the garden level of his parents place.

We showered, got dressed, and went our separate ways. Since that night, Pigeon Bitch has texted from time to time, he’s always the one to initiate. I know there’s no way we could ever actually date even if I lived in NYC, but I guess if I’m ever visiting NYC or if he was ever in Chicago, he’s a nice option to fuck.

Yours Truly,
Kallie Pygus

Spiralled Emotions

Two days after my friend’s going away party, I decided to text Chase. I only had two nights left until I was leaving town for a week to drive my friend Ana to NYC so I wanted to see him before I left. I asked him if he was free that night. He was quick to respond, and in my favor, he said yes. In the text, I told him the first two rounds of drinks are on me because he brought me donuts and got me a drink the week before. He said he wouldn’t turn down free drinks.

After some back and forth banter about how I was going to kick his ass in Pac-Man, we were set on going to an arcade bar. He met me at my place and we walked to the bar together. As we walked to the bar, we chatted about life happenings and did some basic get to know you type questions. It was weird, although we’ve fucked and have already spent a few days together, this was the first time we have done something alone outside of my bedroom.

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We got to the bar, ordered our drinks, which he tried to pay for, but then I reminded him I owed him drinks still, so he backed off. We went straight for Pac-Man. I dominated the first game. He wanted a rematch, then I killed it games two and three. He had the typical guy reaction, surprised that I kicked his ass, but also slightly a sore loser about it. He then decided it was time for Mortal Kombat. We moved on.

At Mortal Kombat, the bar had three versions of it all in a row. We played Mortal Kombat I, II, III one after another. He was a bit butt hurt because I still kicked his ass at those games. After this, he kind of went to play his own game of Mortal Kombat and was kind of being a dick about it. He was salty that I won, and that was kind of a huge turn off. Going to an arcade bar is supposed to be a good ice breaker, not a downer.

I let him do his thing and I played my own game. After he chilled out for a bit, we reconnected. He is aware he’s an ass sometimes. I personally think that some of it is an act. Like someone told him he’s an asshole and now he does shit like get into these moods and be stand offish intentionally. He even asked why I was still hanging out with him that night, he was being a dick and usually people just leave. He called me weird for still being around him. I told him I’m just patient and can give people space when they need to calm the fuck down.

Once we got past this hiccup, things were light and fun again. He then asked if I wanted another drink, I then turned it around on him and said I would go get us another round. When I came back from grabbing our drinks, we moved on to play Frogger. He actually did pretty good at this and won, so his mood was lifted a bit.

Only two drinks in, I was already getting a bit tipsy and I was starving. He offered to buy us something to eat because I bought the drinks. We left the bar and started walking towards a pizza place near my apartment. On our walk, he apologized for his mood earlier, then things got a bit more flirty and fun. Several blocks in, he grabbed my hand and we held hands the rest of the way there. Lately, I haven’t been dating much and I got too used to casual sex. Holding hands felt foreign, but nice.

We got to Chicago Pizza, ordered a couple slices and took them to go so we could drink some more. When we got back to my place, it was deja vu all over again. I went to the other side of the bar, started making us drinks, and the same roommate that drunkenly joined us a few nights earlier decided to join us again. This time, he was a bit happier and less argumentative. Chase and I kept looking at each other like what the fuck, but entertained my roommate yet again.

During this drunken charade, Chase and I kept making faces at each other. Not flirty sexy faces, but funny squinty faces. Once my roommate finally decided to leave, I walked around to Chase’s side of the bar. Before I could even sit down, he pulled me to him to make out. Not only did he pull me in, he pulled me up onto the bar stool, now straddling him, we continued to go at it. He kept reaching up my dress and pulling my top down. My tits flashed the room momentarily here and there, and there was a moment another roommate walked through the bar. I instantly pulled my dress back into place and Chase and I both laughed.

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This recurring thing happens. I bring a guy to my place. We make out in the bar. I have to stop them and explain that any of my eight roommates can walk in from any of the three doors at any moment. The guys generally brush it off like whatever, but every time I eventually lure them to my room.

Chase followed me to my room. This time was a bit different than the past two times. This time he slowed down, teased me, kissed me gently then worked his way from my lips, down my neck, stripped me slowly, then worked his way down to devour my pussy. As he licked me, he paused and asked what turns me on most. I told him to keep eating me and to play and pinch my nipples. He listened. Continued with what he was doing and pinched my nipples hard. The pain shot through my body quickly, intensely, but was followed with a rush of pleasure.

Everything he was doing was fucking amazing. As the feeling intensified, I began to grinding my hips up and down in motion with his licks. He pulled back for a second, licked one of his fingers and slid it in my ass. Now fingering my ass and vagina simultaneously, licking my clit, plus playing with my nipples, a quadfecta (that’s right, a quadfecta not trifecta) sensual experience. My body succumbed to the sensory overload, I tensed up, my back arched, my breathing got heavier, I thrusted my hips up against his mouth, and my vagina pulsated as I came. Finally, third times the charm with Chase.

After that blissful moment, I pulled him up, kissed him, then returned the favor for a few minutes until he demanded sex. We fucked for a while going from missionary to doggy to standing to cowgirl. He came from the sex. I didn’t, but that was ok, oral is usually the easiest way to get me off anyways.

As we laid there post sex, there was yet another shift in the mood. He began to ask if I was staring at him the first night we met. I laughed and told him he was looking at me just as much as I was looking at him. He then brought up how all my friends know who he is, which I could tell all of this was making him uneasy. I tried to reassure him that he was being ridiculous. He eventually backed down and pulled me in to cuddle and kiss a bit before we both fell asleep.

This whole night was a mindfuck. Lots of ups and downs. At this point, it was difficult for me to know what Chase was thinking. Up until this night, everything was going so well. Now it seems as though he’s questioning everything. All of this right before I was leaving for a week and I couldn’t help but think things were going south a bit, but I also think it could have been a small hiccup.

The next morning, we woke up, I kissed him goodbye and we went our separate ways. A week apart to think about the past four encounters and come back with a fresh perspective.

Yours Truly,
Kallie Pygus

 

Will he pass?

Chase texted me the very next day after fucking all night. He asked how late I would be at my friend’s going away party which I told him about when we were talking at his show. I informed him that the party was at my place and I was the host, so I wasn’t able to leave early, but he was welcome to come to the party. He accepted the invitation. I was surprised, yet excited to see him again.

I don’t usually invite boys to things with my friends this early into seeing them, but for some reason Chase was different. I was nervous, I could tell I was already starting to like him, but I also have a pretty thick shell to break through before opening myself emotionally to anyone. Part of me was eager to see him again, the other part was wondering if it was a mistake. What if he doesn’t like my friends? What if he’s anti social and needs to be entertained the whole time? What if he ends up being a total drunken mess? These are things I had no clue of what to expect because I hardly met the guy a week earlier and really have only hung out with him once.

At first he said he would get there by 9, then I told him I would be there at 9:30 because I had to arrive with Ana to lure her into the surprise, so then he said he would come later. When he still wasn’t around by 10:45, I was kind of getting disappointed, but had no time to get down about it. I was having a good time with everyone at the party and couldn’t let a guy not showing up mess with my night.

Around 11pm, I pulled my friend up on the stage to give a speech and make her do karaoke to Nickelback’s Photograph to embarrass the shit out of her. It was an inside joke, she thought that we were going to karaoke that night, and I asked what shitty song she would sing and that was it, but then I surprised her with the huge party at my place. Halfway through the song, Chase walked in. I was on stage with Ana singing a song we hate and that is the first impression he gets of the party I’m throwing.

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As the song ended, Ana stayed on stage for another karaoke song, I walked over to Chase and explained to him the joke behind the song. He then revealed that he actually likes that song. Kind of disappointing that he does, especially because he’s a musician, but this gives me something to make fun of him for later.

I was trying to hang out with him, but being that I was the host, I had a lot of other people to entertain. I made him a drink to get him situated, then ran around to the various people and things that needed tending. This was the first test, is he ok to be left alone in a room full of people he doesn’t know and he passed. He had no problem introducing himself to people randomly and being sociable. I didn’t need to babysit him. Total bonus points.

In fact, he passed every test with flying colors. As the night progressed, he had made friends with several of my friends, like even exchanged phone numbers. He helped me with various drunk people to get them water and make sure they were ok. He knew when to give me space so I can be social with everyone else and when to give me attention. He drank a few drinks, but joked with me to decline a drink by asking if I was trying to get him drunk because I kept giving him drinks. He knew his alcohol limits, paced himself, and stopped before getting hammered. All of these things I was worried about and he did wonderful. The stress and nervousness I felt before has been lifted.

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Throughout the party, whenever Chase had a moment with me, he pulled me in to kiss. When I had to grab something from the kitchen, he came with so we could be alone for a bit to make out. I love all the attention, if only I wasn’t the host, I would have totally pulled him into my room that moment, but couldn’t do that.

At one point in the night, my friends Ana and Ricky pulled Chase aside to talk to him about me. They told him I might come off as tough, but really I’m sensitive and he better not hurt me. When I found this out, I was mortified. Why would they do this to me??? I hardly know the guy and this is something that is bound to send a guy running far, far away.

After confronting Ricky and Ana, they talked me down and said that everything was going to be ok. They said that Chase is really awesome and he didn’t seem too scared by them talking to him. Ana then added, why would he even listen to a word two wasted people had to tell him? I could only hope that they were right.

Once I was calmed from that brief confrontation with the two of them, I walked into the bar to make myself a drink. On my way, Chase was sitting on the couch at the bar entrance. I almost walked right past him, but he pulled me in to kiss him and he told me that my friends gave him some very interesting information. Once again, I was embarrassed, but I tried to hide it. He told me everything they said, but luckily we both laughed about it knowing that my friends were wasted. Extra bonus points.

Everyone at this point was pretty drunk. It was approaching 3am, people were starting to clear out. It was down to Ana, her boyfriend, a few other friends, Chase, and myself. Chase helped me with Ana who was rolling around drunkenly claiming she was a hermit crab. Once I fed her a bagel and gave her lots of water, she sobered up enough for her and her boyfriend to go home.

As soon as everyone left, Chase went straight in for the kill. He started to rub his hands all over my body as we made out. We were still in my kitchen, he tried to get a bit more handsy, but I stopped him. As hot as sex in a public place can be, I also would like to not have any of my roommates walk in on me. I stopped him and took him to my room.

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Once again, we fucked all night. There were some small breaks filled with pillow talk, then more sex, then some sleeping, but then he’d wake me up for more sex. We even made a brief sexual appearance at 5am in the bar, but the couch in the bar proved to be quite loud, so to avoid waking anyone up, I pulled him back to my room. The sex was plentiful and good, but once again, I still couldn’t come. I wanted to, but there’s a learning curve and also a layer of trust that needs to be built for me to ease up enough to come.

The next day, we woke up at about 1pm. He had to get home to get ready for work. I walked him to the front door, then made my way back to my room and passed the fuck out. I was wiped yet again.

The early stages of meeting a new boy are always the best.

Yours Truly,
Kallie Pygus

Wingmanned by an Entourage

What ever happened to Boy #1 and Boy #2 from my post Failing my Break From Boys? Well nothing has happened with Boy #1… but if I wasn’t so occupied with Boy #2, I might have had more time to write blog posts.

About a month ago I met Boy #2, Chase, we continued to message back and forth on Facebook for an hour or so the first night we met, I gave him my phone number, and then texted well into the night. When he messaged me, at one point he sent a cat sticker with a donut. He found my sweet tooth. He later invited me to his band’s show, I told him I would go if there was donuts.

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The next day, my roommates had band practice and one of them texted me saying to guess who has a practice space next to them. I quickly guessed Chase’s band. I was right. I took a screenshot and sent it to Chase because the night before we had played a little bit of a guessing game which I kicked ass at so I had to brag about this guess being correct as well. We then texted back and forth with some flirty banter which lead back to my sweet tooth. He then questioned if there was more to me than just my love for sweets, I ended the conversation to go to bed and leave some mystery.

Thursday couldn’t come soon enough. I was eager to see Chase again, but I knew I had to be patient. Being that his band was performing, it wasn’t really a date, he just said I should come see them. They were playing at a bar in Wrigleyville… not quite the scene my friends hang out in so the challenge I faced was getting at least one of them to come with me so I wasn’t showing up alone.

I asked my roommates. All of them refused. I asked my gay husband. He said maybe, which usually means no. I then asked my friend and her boyfriend and another friend. They were all reluctant because Wrigleyville, but I did just give them a ride to and from the airport, so one of my friends and her boyfriend agreed, the other said maybe.

When Thursday came, my friend and her boyfriend met up with me before the show to grab dinner beforehand. I haven’t heard from Chase at all since Sunday night. My friend Ana wanted me to text him to confirm what time they were playing. I was reluctant because I don’t want to come off too desperate. To make it light, I sent a donut fact meme and asked if he had a donut waiting for me at the bar. He said I would have to come to find out, opening it up for me to confirm what time they were going on.

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While at dinner, my other friend that said maybe texted saying she was on her way. Then my gay husband called and asked if he could bring a friend. So now, even though I really only needed one wingman, I had an entire fucking entourage of five people coming to the show. I wasn’t sure how I felt about having so many people, but it was too late to tell any of them not to come.

The three of us that went to dinner showed up to the bar first. He was with his friends at a table, so the three of us grabbed some bar stools and ordered drinks. He came up and said hi baring a Stan’s Donuts bag just for me. I excitedly thanked him and introduced him to my friend and her boyfriend. We chatted a bit, then he got back to his friends.

His band was about to start, we made our way to the tables near the stage. I snacked on the donuts and watched as he got behind the drums. While his band was playing, my other friend, my gay husband, and his friend showed up and sat by me at the table. When Chase finished his set, his band packed up, he hung out with his friends for a bit, then came by us to see what we thought. I introduced him to the three newcomers. Now that there was six of us, the table was pretty full.

Chase stood next to me for a moment to chat, but I was now also entertaining five other people who were supposed to be wingmanning me, but somehow they failed to get the memo because they all wanted my attention. He excused himself and went to the nearby table where his band and friends were sitting. I gave my friend the ugh look, and she realized they cock blocked me. My girls and my friend’s boyfriend then decided to go to the bar next door temporarily to play skeeball. Now it was just my gay husband and his friend leaving the table a little more empty. A few minutes later, Chase came back to ask why my friend’s ditched me. I laughed, it was deja vu from the night we first met.

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The next band started. My friends came back, but my one friend and her boyfriend said their goodbyes pretty quick, leaving it with me, my gay husband, his friend, my other friend, and Chase. He offered to by me a drink so I told him my order and he went to the bar. When he got back, he sat next to me and we continued to flirt a bit and then the band asked everyone to get up and stand closer to the stage. We did so, and my girlfriend and I danced a bit to the music while Chase watched.

After the bands were done, my gay husband and his friend left pretty quick. My girlfriend hung out with me for a bit, but Chase lingered close by. He joined in on our conversation for a bit, then excused himself to go buy a band tee from the last band, but promised he would be right back. While he was gone, my friend asked if she should call her Uber, I told her to get on that because it was obvious Chase wanted to hang out with me.

She requested her ride. Chase came back, she then announced her ride was waiting out front. She said bye. Chase and I got talking. Then his friend interrupted to see what he was planning on doing. He hesitated and said he would catch up with them later. He then told me his friends wanted him to come out. I told him he could go, but then he said he would rather hang out with me. I said we could both go hang out with his friends. He revealed he lives in the suburbs, so that would mean going out there instead of staying in the city.

It was already 1am, so not worth going to an actual bar to have it close an hour later, so I then invited him to my place. I have a bar, so the drinks are free and the night could go as late as we wanted it with no restrictions. He agreed to come over.

We had both driven to the bar separately, so we both drove to my place in our own cars. He parked out front at the pay to park. I parked in the back and walked around to the front to meet up with him. We went up to my apartment, I gave him a tour, then took him to the bar and poured us each a drink. I sat behind the bar and he sat on one of the bar stools across from me.

Chase and I got talking, but not long into our conversation, one of my roommates drunkenly joined us. We entertained him for a good hour arguing about an upcoming party we were throwing for a friend. Chase played along and helped me with my argument. He was winning on every front; looks, charm, humor, and now defending me without even knowing me.

After the argument subsided, my roommate finally quit and went to bed. Chase and I were finally alone. It took all night to get my friends to give me space with Chase and then an hour of arguing with my drunk roommate before we actually had a moment to ourselves. It got quiet for a second. The sexual tension was so thick you could cut it with a knife. Chase then stood up and leaned over the bar to kiss me. We kissed for a moment, and then I pulled back and walked around to sit next to him, before I could sit down, he pulled me in and we began to make out. Another roommate walked in, I pulled back and laughed. I told him we should go to my room to avoid having any roommates getting scarred for life.

We got up and took it to my room. We fucked all night and then some. It was good, not great. I didn’t come, but I rarely do on the first night of sex. It was approaching 6am, I had to be up at 8am to shower and go to work. Even in the summer heat, he spooned me until my alarm went off. We woke up, he lingered as I said I had to jump in the shower and get to work. I then invited him into the shower, he joined me. We couldn’t stop touching each other and kissing the entire time. I was running late for work, I had to stop him from rubbing my body. We got out, both got dressed, and I walked him to the front door where we made out some more. I then went to gather my stuff and left out the back door to my car.

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I was exhausted, but staying up all night with Chase was well worth it. There’s more to tell you… I promise I will write again soon.

Yours Truly,
Kallie Pygus

And then he called me…

Heyyy….

It’s been a while. I know. I’ve been a terrible blogger and have lots to tell you. I will get back to Capture the Flag Boy (funny enough, I ran into him at a liquor store this past Saturday). I need to fill you in on some other happenings first.

Let’s start with Shane….

Shane (aka Soccer Player, introduced in Call Me!) and I have been texting more and more the past several months since he started bartending. We haven’t seen each other since last fall, but we text basically every other day and he’s been calling me every once in a while to bitch about customers.

About a week ago, it was one of those nights. He needed to call me to tell me what went down. It was a Sunday night, so pretty slow at his bar. One of his last customers though was so intoxicated I guess he puked all over the bar… story aside, Shane called to vent about this, then he asked if I was going to be awake for a while. I told him I was up, not planning on sleeping yet. He then asked if he could come over and that he would pick up some beer on the way. I agreed.

About 20 minutes later, he arrived. We went to my bar, cracked open the beers and both caught up. Like I said, it’s been several months since we’ve seen each other in person regardless of texting and the occasional phone call about bartending, we still had a lot of other life things to get filled in on.

Nearly two hours and a few beers later and we are still talking, laughing, and having a good time. We were both on bar stools, facing each other, our legs lightly brushing the other’s as the chair swiveled. As we continued to talk, he started to run his hand on my knee and played footsie with me. He then leaned in and kissed me.

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His lips pressing up against mine with the perfect blend of lip suction and tongue all while running his hand up my thigh, around to my back, and up my neck. He has a way with his hands and lips. I missed tasting him and it felt so good to have my lips locked with his again. Several minutes of this, I pulled away and invited him to my room. I got up and he followed.

We got into my room, I took off my sweater right away as he sat on the edge of my bed. I then straddled him and went in to kiss him again. We made out as I grinded him slowly with my hips pressed against his. Oh my god, he is by far the best kisser I’ve ever been with. I wish we were more compatible relationshipwise, but that’s a different story of which I will fill you in on later when I flash back to meeting Shane.

As things heated up, he flipped me over. Now I was laying on my back, he kissed me, then made his was down my neck and to my stomach to then slowly take my shirt off. As I leaned up, he took my shirt off and continued to kiss me as he unhooked my bra. Everything he does is seamless. He laid me back down and kissed my breasts gently, then licked down my stomach and pulled my pants off and dived head first into my vagina.

Surprisingly enough, when I first met Shane, we went on several dates and had sex multiple times and had sex randomly since, but he has only gone down on me for literally a brief minute at a time so I never quite got the full experience to be able to know how good he’d be. This time, he stayed down there. He didn’t come straight in for the fuck, but wanted to give all he could with his mouth.

With the way he kisses, I thought he would be a pro down there, he was good, but not the best I’ve had. He uses too much pressure for my liking. I think it has something to do with the fact that he’s an athlete and probably doesn’t realize his own strength sometime. It felt good, but there was no way he’d make me come like that, plus I was craving his throbbing cock inside of me.

I pulled him up and kissed him. He grabbed the condom from my night stand, put it on, then continued to kiss me. He slowly inserted his dick in me. His penis is fabulous. A good 7-8 inches, thick, and uncircumcised (which I have recently began to prefer). Everything about his penis is the perfect size for me.

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As we fucked, he continued to be seamless. He’s great at going from missionary, to cowgirl, to doggy style, to reverse cowgirl all without saying a word or taking his dick out. He just grabs hold of me and spins me every which way to the position of his liking. The athlete in him that I think makes his oral pressure way off has its benefits because his moves are smooth, he’s strong, and has great endurance.

When I got on top, he came pretty quick, but that was round one. I know from our history he is good to go all night. We laid there and pillow talked for a minute. He then started to rub my breasts and worked his way down to my clit with his fingers. Hardly a minute later, he was ready for round two.

He turned me around and slid in from behind doggy style. He knows my body. Knows I like being dominated. He pinned me down, holding my arms behind my back with one hand while, using his other hand to smack my ass and grab my hips. Everything he was doing was amazing! As much as I enjoyed it, he had to ruin it by saying “Come for me baby!”

So much was wrong with that. First of all, I hate being called baby. Baby is up there with being called man or dude by a guy you’re seeing. Second, as I’ve said before (see Stop Acting and Start Reacting) I hate being told to come. That fucked me over. I was close but not gonna happen at that moment any more. He came. I didn’t. We rolled over and I told him he should know better than to tell a girl to come (I omitted the baby part, that usually wouldn’t ruin it for me by itself). He apologized and knew he shouldn’t have especially because I’ve told him that before.

To make it up to me, he asked what I wanted him to do to me. I explained I come easiest from oral, but that he needs to ease up on the pressure while he’s down there. I also told him I like being completely submissive and teased. We talked a brief moment about my kinks and I realized how vanilla he actually is. As naturally dominant as he can be, he’s never done any actual kinky stuff. He said he’s only played with a vibrator once, he’s never played with bondage, cuffs, nipple clamps, other toys. To not rush him into any of that, I told him to restrain me, bite my nipples, and tease me till I’m begging.

Once he found out I like pain, he got really into biting my nipples, more so than I expected of him. It was hot, but almost excessive. He got me super worked up. He avoided my clit just as I told him, kissing and licking my thighs and stomach and biting and pinching my nipples. He then finally licked my clit with just the tip of his tongue and I pressed my hips up. He hardly got a taste of it, and I gave in. “Come up and fuck me!” I demanded, he gave up too soon and came up. I wish he was more dominant in that moment and told me to shut the fuck up so he could continue to eat me, but he listened instead and put a condom on to fuck me.

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He slid in, I was soaking wet. We were both worked up from the tease, biting, and oral. It only took about a minute of having his dick inside me before I felt my body start to tense, my back start to arch, my breathing got heavier, and I grabbed his ass to pull him in deep as my vagina started to contract. The pulse from my contractions strained his dick and he came as well. We both came. Success.

He laid on top of me, dick still inside for a good minute or two. We kissed gently. Oral sex and kinks aside (which I’m sure with more time with me it could be perfected), he is one of the best lays I’ve ever had.

The next morning, he kissed me goodbye and left. Since then, it’s been back to our normal routine. Text every other day or so to bitch about work. Nothing out of the ordinary, nothing awkward about it post sex. This was nice. What I enjoy most about Shane, he’s the occasional masterful fuck with no strings attached.

Once again, Shane and I are texting as I write this… I hope this ties you over. I will write more soon.

Yours Truly,
Kallie Pygus

Capture the Flag Boy and MIA Texts #2

May 13th I got a text from Caden aka Capture the Flag Boy. The last time I heard from him, he was trying to hang out Valentine’s Day, then before that, it was December. In today’s casual hookup culture, people come and go. One second, you’re hanging out regularly, the next, the person is MIA and suddenly reappears months later. This is post two of five about Capture the Flag Boy and MIA Texts.

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After the first date (see Capture the Flag Boy and MIA Texts #1), we texted back and forth for a few weeks trying to make plans to hang out again, but our schedules never aligned. We both eventually gave up and I almost totally forgot about him, that is, until a month later. Capture the Flag Boy added me on Facebook about a month after we stopped texting each other.

I was a bit thrown off. Generally I don’t add guys on Facebook I’ve only been on one date with, especially if we met online. I accepted it, then texted him to sarcastically question the befriending. We then caught up via text and he told me he was volunteering as a stage hand for a theatre and offered me free tickets to the show. I accepted and gave him a date for the show a couple weeks later.

The night before the show, my roommate Andy had a friend over photographing him. I have a bit of photography experience myself, so when I saw the strobe in Andy’s room, I was eager to see what was going on. I watched as they finished up their shoot, then I went and sat to do some work in the living room. Once they tore down the lighting, Andy was getting dressed for them to go out that evening. His friend, David, came out and introduced himself. David is about 5’9″, much shorter than I usually go for, but still taller than me. He’s got freckles, light brown eyes, brown hair, and perfect teeth with a great smile. Very sweet and boyish features.

David told me about his experience as a photographer and how he went to college with Andy. We got talking about all things photo and the conversation was flawlessly smooth. We instantly became comfortable with one another. As Andy came out and saw us talking, he interrupted and said I should come out to the bars with them. I agreed, got dressed, and we all headed out.

Andy was DJing a set at the first bar of the evening, so when we arrived, he went to the DJ booth and David and I were left alone at the table together. We got chatting again and naturally fell into light, flirty conversation. I was trying to be supportive of Andy as he was DJing, but was so distracted by David. When Andy came down from the booth, David and I both congratulated Andy, and Andy stole David away from me for a smoke.

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When they came back, Andy said we should all go dancing. I agreed and we were off to the next bar. We walked in, David asked what I wanted to drink and he made his way to the bar as Andy and I made our way to the back dancing area. Andy told me that David liked me, which was obvious. He then proceeded to tell me how good of a guy he is. Caveat, David doesn’t live in Chicago. I didn’t care, I really liked him.

David came bearing drinks. We sat on the couches in the back of the club and sipped and chatted some more. David now sitting right next to me, he put his hand on my thigh, gently rubbing it. He was sweet, but obviously nervous. It seemed like he was unsure of how to navigate the scenario.

Several of our friends showed up. I got up and gave hugs, and then they pulled me to the dance floor. I looked at David and did a come hither finger motion. He followed us to the dance floor. It was soul night, so it was lighter and more harmless than a night of grinding at the club. David and I danced and laughed and danced some more. It was a 4am bar and we didn’t realize the time till lights went up and it was last call.

Andy, David, and I waved down a cab and went home. David, who was planning on crashing on a couch, asked if he could crash on my bed. He said that we didn’t need to have sex or anything, he just wanted something more comfortable than a couch. I laughed and told him of course, I was already planning on having him sleep in my bed.

We got home and I took him straight to my room. I got down to my tank top and underwear and he stripped down to his boxers. We hadn’t kissed or anything at this point, but we were already half naked. I climbed into bed. He followed. We laid there and started talking. If all the talking and dancing wasn’t enough, we continued. After about another hour of talking, he finally made his move and kissed me. We ended up making out for a while and pausing every once in a while to chat more. There was some feeling each other up, but he was very hesitant with every little thing he did. I wanted to sleep with him, but I was also kind of liking the slow pace he was setting.

After a couple hours of this, we realized it was 7am and he had to wake up by 10am. He spooned me and we cuddled then next three hours until his alarm went off. The next morning, we ate breakfast, he said his good bye and told me if I was ever near him in Bloomington, I should call him. He had one more night in Chicago, but already had plans with another friend.

I went back to bed and then several hours later woke up to get ready for the theatre. I brought my friend Geoffrey to the show. It was a hot summer day, I dressed up in a sexy short black, red, and white paisley dress and black wedges. We arrived, got our tickets from will call and found our seats. There was absolutely no cell phone reception in the theatre, so I couldn’t text Caden to thank him and say that we made it, but he found us anyways. He was up in the balcony so he yelled down to say hi. Oh my god, I forgot how sexy his smile was. He black and puerto rican mixed, long maintained dreads, angular facial features, tall, fit, and great eyes.

During intermission, Geoffrey and I went outside to chat and so he could smoke a cigarette. I told Geoffrey everything about David and Caden. I explained I just met David last night, but kind of wanted to see if him and his friend wanted to meet us for drinks, but I also wanted to tell Caden he should join us as a thank you for the tickets. Geoffrey helped me and said I should text David and see what he says because he only has one night left and if he can’t I can then tell Caden. This seemed like a great idea, so I texted David.

We then went back into the receptionless theatre and watched the 2nd half of the show. When the show ended, Geoffrey and I made our way out, but Caden stopped us along the way. We thanked him, I introduced Geoffrey to him, and said I would be right back with them so I could step out to the bathroom to check my phone. Once in the bathroom, I tried checking my phone, but because of the lack of cell reception, there was nothing. I went back out to the boys. Caden was kind of lingering, I then thanked him again and told him we should get drinks sometime next week because I had a friend in town that night and already had plans with him, hoping that David would still message me. We said our goodbyes and Geoffrey and I walked out.

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As soon as we got out of the theatre, I got the text. David wasn’t able to make it out that night. I blew off Caden with hope of seeing David, but that failed. I was bummed, but then went and danced my sorrows away in Boystown with Geoffrey.

After that night, Caden disappeared yet again for another month… a recurring theme with Capture the Flag Boy. Boys that go MIA instantly fall into the red flag category, yet for some reason he still had me intrigued.

Yours Truly,
Kallie Pygus