When Two Boys Meet

Fast forward about a month to early August….

I haven’t seen Neighbor Boy at all since I met him a month earlier, which was kind of disappointing, but then again we didn’t exchange numbers or anything. During this time, I went on several tinder dates, saw Chase a time or two, and have been hanging out with Shane more and more platonically. I had so much going on with other boys that Neighbor Boy was the last guy on my mind.

There’s always extra bartending gigs in the summer with festivals, so Shane and I got to work together for a friend’s booth at Taste of Lincoln. Throughout the day, we were mildly flirty, but more friendly and comfortable with each other than anything else. We bonded over both being bartenders; however, during this same gig, he told me he started applying for full-time jobs again and even had an interview, so would be quitting bartending soon.

Although I still find him very attractive, it seems like Shane and I got to a point where we’re friends. Or so I thought… He was very confusing throughout the day. Like he kept giving me this look like he wanted me. A few hours into the day, it slowed down and I sat for a moment and got my sunblock out to reapply. As I went to put some on my shoulders, he walked up behind me and began to rub them for me and spread it down my upper back. Shane is the best with his hands, his massages are to die for, so I relaxed and tilted my head down to let him continue to rub my back. Some people walked up to the booth, Shane stopped massaging me to take their order. I quickly finished adding my sunblock and went back to the front of the booth.

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Our light banter continued, but it was still hard to read. I want to be able to be friends with him, and I think we were doing well for a while minus the times we ended up fucking (even then we easily continued being friends). On the other hand, I really want to fuck him. I miss kissing him, holding him, having him massage me, and I miss feeling his body against mine as he fucks me. He is still one of the greatest lays and I know we couldn’t ever be in a relationship with each other, but I wish we could continue to fuck.

As our evening wrapped up, Shane and I cleaned up our booth, closed up, and headed out. We both walked towards the redline and he asked if I wanted to grab a drink with him. I told him there was a party going on at my place, but that he should come by and we could have a few drinks there. He accepted the invitation and we hopped on the next redline to my place.

When we got to my place, the party was packed, we squeezed our way to the bar and I grabbed Shane a beer and made myself a whiskey coke. There was a band playing that night, so it was pretty loud. My roommates needed some help with the party, so I was running around picking things up and grabbing some friends some drinks. During this, Shane and I kept making eye contact. I pulled one of my other roommates aside to tell him to pick up my slack and let me chill with Shane. He agreed and I got back to entertaining my guest.

I sat at the bar next to Shane. He told me how sweet the party is; it was his first time at one of our parties. I laughed and tried to keep it platonic, but I kept thinking about how I wanted him. The band ended, I went back behind the bar and grabbed Shane and I each another round. As the next band started, I took Shane up to the roof, hoping to find a quieter space.

When we got to the roof, there were about twenty or so people up there, but definitely a bit more quiet and tame compared to inside. I lifted myself and sat on the ledge on the front of the roof, he sat right next to me. He was closer than I had expected, but it was a pleasant surprised. His leg against mine, we started with some bar talk, ranting about various customers and telling tales and horrors of our bartending experiences. This quickly changed to a more flirtatious banter and got to a point where there was a comfortable silence. We locked eyes for a moment in our silence, but at this very instance, Neighbor Boy and his roommate Mike walked up.

I stood up and gave Mike a hug and said hi, then looked and Neighbor Boy and said hey to him as well. I introduced them to Shane and we all got talking. It was Neighbor Boy’s first time on the roof. He asked me how to get a key for the roof because they were having a party next weekend. This was getting complicated, I wanted Shane, but couldn’t resist my flirtation with Neighbor Boy. I’m terrible at hiding it. To be a little sly, instead of flirtatiously giving Neighbor Boy my number, I told Neighbor Boy that Mike has my information or to find me on Facebook and I could get him a key. At that moment, Neighbor Boy got a bit weird, said thanks but then said bye right away and left.

Mike stayed up and chatted with Shane and I a bit more. He told me that next weekend is Neighbor Boy’s birthday party and I should come. I told Mike I have a camping trip planned with my family, but if for whatever reason I’m around, I would stop by. The conversation wrapped up and Mike went to talk to another one of my roommates that was on the other side of the roof.

Shane and I sat back where we were at, but now he was a good foot or two away from me. He took a sip of his drink, I took a sip of mine. At this point, he said he should finish his drink and head out. A little disappointed, I jokingly asked, “Why? Is it past your bedtime?” He laughed, but then told me he was going to meet up with some friends. I let it go. He finished his drink, we hugged, and said our goodbyes.

That was the last time I saw Shane. He got the job he interviewed for, so he quit bartending. As a result, we texted less and less. He no longer had bartending stories or customers to bitch about. We no longer had common ground. He is back to being a soccer playing corporate employee with a 9-5, while I’m still a free-spirited artist and curator that works odd and end jobs. Every rare occasion we will text one another, but usually it’s just a one-off meme or quick text. Nothing more.

Although this boy was no more, you know what they say; when one door closes another opens.

Yours Truly,
Kallie Pygus

Tinder Douche #2

Tinder Douche texted me the very next day to inform me how he couldn’t wait to nap. I wore him out. I threw it in his face that I slept till 1pm. There was some back and forth flirty banter, but he obviously was more interested in me than I was him. If it was up to me, I would have never seen him again. The sex was pretty good, but him as a person was forgettable, but alas, I was bored and the sex was good enough to keep him around if he’s hitting me up. We texted back and forth for the next two days and he finally caved. He needed me.

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It was obviously a booty call. It was nearly 1am. He has been drinking and in the suburbs dying of boredom. He was trying to tell me he needs an excuse to leave. I told him he could make some shit up and just leave, he’s an adult, he can do whatever he wants. He was then trying to tell me that he wants the excuse to be me, he really wanted to see me right at that moment. He begged and said he would pick me up and drive me home, and begged some more until I said yes. At the moment, it was cute. Looking back, it was pathetic.

On his drive back to the city, there was a car accident. To show me that he wasn’t lying or some shit like that, he decided to facetime me while he was driving. What a dumbass!? Either way, he showed me that the cars were up in flames and he was stuck in traffic because of it. I wasn’t too concerned, he would get there whenever he got there.

At about 2:15am, he picked me up. I don’t know why I agreed to let him pick me up. I should have just drove myself and met him at his place. But that is how life goes, you make decisions and shit happens. As we pulled up to his apartment, he bitched about the lack of parking. All I could think is how he lives in Chicago, and even the cherry to top it, he lives in Lakeview, of course parking is tough to find. Stop your bitching and get over it.

He parked his car about three blocks down from his apartment and on our walk, he wouldn’t stop his complaining about the parking situation. Oh my god, I wanted to shoot myself. This little prick is so fucking annoying and somehow I decided to hang out with him again. On the outside, I faked it. I faked it so hard and put a smile on and said “Sorry, this does suck,” to get him to shut up about the parking. On the inside, I was cussing him out, telling him to get the fuck over it because this is how shit is in the city, sorry if you just moved here a few weeks earlier. Boo fucking hoo that you can’t find parking right in front of your apartment.

We got to his place, he went straight to the kitchen and told me to have a seat in the living room and he was grabbing water. I assumed he would get me a glass too because he asked if I was thirsty and I said yes, but he walked in with just one glass which he was hogging. OK? So I spoke up and grabbed the glass from him and drank the water I had asked for in the first place.

He turned on ESPN… Once again, I was annoyed. I spoke up again and told him I didn’t agree to come over so he could catch up on the sports highlights while I just sit there. He apologized for being inconsiderate, then he surprised me by bringing up art. At first I thought he was being genuine and actually interested when he asked about my opinion about some art that was up for auction at Sotheby’s, but I quickly realized he is a complete imbecile. He was trying to argue with me about how a child could paint the paintings that were up for auction and he couldn’t understand what was so significant about the work even when I schooled him with some art history. His only response once I shut him down was, “Well, that’s not my problem.” Which made absolutely no sense.

I should have left then, but I didn’t. Sometimes I wonder why I make myself suffer. Once the art argument dissipated, we went to his bedroom. He quickly went in to kiss me and the night quickly escalated. All this pent up anger and aggravation I had towards him made the sex more aggressive and hot. He pulled my hair and kissed my neck and stripped me naked and bit my nipples and played with my clitoral hood ring. He was in control and very dominant, a huge turn on despite the overall tone of the night so far.

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He then stripped himself down naked, I quickly noticed he had shave since I saw him last. Not only did he shave his dick bald, he shaved his entire chest. Huge turn off, but I was letting it slide because he quickly plunged his face between my thighs and took his mouth to my clit. And this is where he lost me even more. He had no clue what he was doing with his mouth. I literally had to tell him not to bite my piercing. How can he be so good with his fingers and suck with his mouth? On top of it, once I got him to chill with the chomping on my vulva, he got to a decent licking, but nothing spectacular, he didn’t use his fingers at all. I told him to add his fingers and he seemed confused, like how could someone finger and eat pussy at the same time?

Once I got him to add his fingers, things seemed to be kind of better, but hardly comparable to what my expectations were for him based on his other skills. Maybe five minutes has gone by, and that might be exaggerating, before he gave up. He came up and gave me a “suck my dick because I just ate your pussy look.” I looked at him and told him his job wasn’t done. He then told me, “You’re lucky I just ate you that long, I rarely eat pussy.”

No fucking shit. Of course he doesn’t eat pussy. That explains a lot, and now you’re expecting me to suck your dick? I told him to get back down there if he expects me to suck his dick. He then asked if we could 69 instead. I reluctantly agreed. He was doing somewhat better, but he also kept getting sidetracked by what I was doing and kept trying to push his head aside so he can watch me blow him. I was getting no where and I wasn’t about to let him get off without hardly doing shit for me, so I stopped, rolled over, and told him to grab a condom.

He bitched about that too, telling me he was so close to cumming. I told him he’s lucky I’m still even there, then he stopped his complaining and grabbed a condom. Once again, he fucked me hard. Pulled my hair. Spanked my ass. Pinned me down. Pinched and bit my nipples. Played with my clit. It was hot. I was close. I flipped us over, told him to sit on the edge of the bed, facing away from him, I placed my hands on his knees, and sat on his cock, sliding him into my vagina. I pulled his fingers to my clit, and his other hand up to my nipples to pinch them as I rode him hard. I came. He came. We both came.

I got up, and laid down on his bed as he took off the condom and cleaned up. He then laid next to me and said he was getting tired. I looked at him, and said “Ok? So give me a ride home.” He then said “Not my problem, sounds like a you problem. Catch an Uber home or something.” I cussed him out and told him if he wasn’t giving me a ride home, I could have driven myself. Not that it was that far of an Uber ride or anything, but the ass really had some nerve.

He then proceeded to tell me to leave. I got dressed, went to the bathroom, and when I got out, he was introducing me to his roommate. His roommate looked me up and down and asked Tinder Douche, “So this is the hot bartender you told me about?” as if I wasn’t even there. Tinder Douche continued this side conversation with his roommate right in front of me and told him, “Yea, she’s pretty good in bed… too bad she wouldn’t finish blowing me.”

I then told him off right in front of his roommate, “First of all, you fucking suck at eating pussy. Secondly, grow your fucking body hair. Trim it, don’t fucking shave it. You look like a prepubescent boy and your entire body felt like sandpaper rubbing against me. Thirdly…” This rant of mine continued for a good minute or two.

His response, “Not my problem, sounds like a you problem.”

I didn’t say anything after that. I grabbed my purse and walked out and called a Lyft. A couple minutes later, as I stood there waiting for my ride, Tinder Douche walked out to apologize. He tried to comfort me and tried to kiss me. I was beyond my limits, and pushed him away and called him a fucking asshole. He then kept trying to say he was just fucking with me because he knows I can talk shit and hold my own. I ignored him. He kept talking at me and luckily this only lasted a minute because my Lyft driver pulled up. I walked towards the car, he grabbed my hand, I looked back angrily and pulled my hand away.

As soon as I was in the Lyft, I was relieved to be on my way home. That was a night from hell, and I was glad to be done with Tinder Douche. Not long after I left, he texted:

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He didn’t respond to that text. His next text to me was an emoji crying and a gun, which I thought was him saying he was committing suicide as a dark response to me chewing him out, but I guess he was trying to say he was tired? Either way, I told him he could crash and burn like the cars he saw on the way to picking me up. Dark? Yes. Sorry. But Tinder Douche is dead to me.

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

Tampa Boy Encounter #3

I met Tamp Boy (Ryan from Red Flags Equal Fun) Sunday April 24th and hung out with him a total of four times before I wrote him off Tuesday May 3rd. The first time, I realized how many red flags there were going in, but still had my fun. Then encounters two through four were a downward spiral, but I guess that is expected when there are so many red flags. This is part two of a three part post for Tampa Boy Encounters #2-4.

Tampa Boy Encounter #3

The day after my second encounter with him, I texted in the afternoon to be flirty; I told him he got me too high and right after he hung up I took my vibrator out. I was still horny from not getting laid the night before. He responded several hours later around 6:30pm to tell me I’m cute high and that it turns him on that I masturbated right after I got off the phone with him. I responded not long after, but then it took Tampa until around 11:30pm to text me back. Red flag. I was exhausted and had to work early the next morning, he missed his window. He tried to get me to come to his hotel. I told him no, it was too late and had to be up early. After texting back and forth for about an hour, I told him goodnight and told him that I was bartending for a concert the next day and that he should come. He didn’t respond, but that was ok with me.

The concert started at 9pm. Tampa still hasn’t responded, but this worked in my favor. A guy I had a huge crush on in college showed up and sat at the bar. Excited to see him, I gave him a hug. Once we got talking, the conversation didn’t stop the entire 3 hour show (surprisingly not a lot of people were drinking that night, mostly just there for the music). A friend of mine even did some sneaky detective work and found out that he is recently single. I met Landon, College Crush Boy, my freshman year. I was instantly drawn to him, but I had a longterm boyfriend at the time so nothing ever came of it while I was in school. After I broke up with my boyfriend a few years later, I ran into Landon several times at various parties and events, but he had a girlfriend. Now we are both single, but I am supposed to be on an emotional break from boys. We will see if I can refrain, but I don’t know if I want to.

When the show ended, Landon got ready to leave, but lingered and told me to come give him a hug. When I hugged him, he pulled me in, the hug was long, I pulled away, then he pulled me back one last time, hugged again for a brief moment before he let go.  He then put his hand on my arm, squeezed it gently, and told me to keep him posted for future shows. My crush on Landon has been lit yet again. I will let you know if anything happens.

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Shortly after Landon left, my guy friend Shane (introduced in Call Me!) texted to see what I was up to. I told him I just finished bartending for a show, but was still hanging out for a few drinks if he wanted to join. He slacked on responding. About an hour later I still haven’t heard from him.

My phone vibrated, excited, hoping it was Shane, I was caught off guard to see that it was Tampa Boy. I ignored it. I told myself I would give it another 15 minutes before responding in case Shane finally texts. Only after like 5 minutes of waiting, Tampa calls. I answered reluctantly. He asked what I was up to and said he wanted to see me. I agreed and he said he would be at the bar in 20 minutes.

Shortly after Tampa called, Shane responded to the text. He was just finishing work and he texted to tell me about his night. We corresponded briefly, then at one point I texted “Fuck you!” and he responded with, “Sure, why not?” Shane and I haven’t slept together in several months, the last time we actually hung out a couple months ago it was platonic, and since then, we haven’t actually hung out, but we text almost every other day. OF ALL THE NIGHTS HE WANTS TO HANG OUT I ALREADY HAVE A GUY COMING OVER! A huge what the fuck moment. I told him I was tired and was about to head home to end the conversation. Fuck! That sucked ass.

Now that I blew off Shane, I was still waiting on Tampa. It’s been over an hour from when he said 20 minutes and he still wasn’t there. Red flag. I texted and told him because the bar is only a block from my place, to just meet me at my apartment. He said he was just about to pull up, so I met him out front and we walked the block home.

Total deja vu. As we walked in, we went straight to my bar, I made us each whiskey cokes, and he packed a bowl. He went straight into talking about himself, and I just zoned him out, thinking about ripping his clothes off. He moved us to the couch. Made his typical advance. We made out for a bit. He asked about going to my room. I laughed. This time I explained, “My room, although messy, isn’t terrible. The problem is that I live in a space that has paper thin walls and 8 roommates. I’m fine with fucking in my room, but I avoid it. What about your hotel?”

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He then explained his assistant was at the hotel room, this time no son though. He said that she was only in town for a couple nights of the few weeks he was in town, so instead of getting a second room, he got a double queen room for the entire duration of his stay. He then tried to say, “We could go to the hotel. She’s probably sleeping. I can sneak you in. If she wakes up, she would probably be turned on.” HUGE red flag.

I wasn’t having that. I told him fuck no, then agreed to let him in my room. We got up from the couch and went to my room. As we both stripped, I thought he was joking when he said, “Well, because your walls are paper thin I will just have to make love to you as if you were my wife.” Another HUGE red flag.

“What?!”I asked.

He laughed, then said, “Never mind.”

We started to make out. He kissed his was down my body and down between my thighs. The way he worked his tongue on my clit reminded me of why I put up with every red flag he has thrown my way. Eating away, he licked for several minutes, getting me worked up, but didn’t let me cum. He licked his way back up my body and proceeded to kiss me. Then he rolled over and laid there, dick out, looking at me then at his dick as if he expected to be blown. I went ahead and blew him. He enjoyed every bit of it, then told me to stop so he could fuck me.

He got up and grabbed a condom from his jeans, he put it on then got on top, missionary, and slowly entered, kissing me gently. I’m not opposed to soft, “love-making,” type of sex, but in this instance, it was a huge turn off. I couldn’t help but to think about the wife comment he made a few minutes earlier. I pushed him up, and rolled him over to fuck him the way I wanted to fuck. He grabbed me, wrapping his arms around me to slow us down. This struggle of him wanting sensual slow sex and me wanting to be fucked rough was not working. I finally gave in and let him get back on top. He came. I didn’t.

We laid there for a moment, a bit of kissing, then just cuddled in silence for several minutes. He broke it by asking if I would miss him when he went back to Tampa. I didn’t say anything, just chuckled. It was now 6am, he realized the time and then said he should probably not fall asleep because he has to check out of his hotel at noon and still needs to pack. He asked for a ride, but I was too tired. He caught a Lyft instead. I passed out and was kind of relieved that he was headed back to Tampa that day.

Fuck! These red flags were supposed to be fun for a night, not draining for a week.

Yours Truly,
Kallie Pygus

Tampa Boy Encounter #2

I met Tamp Boy (Ryan from Red Flags Equal Fun) Sunday April 24th and hung out with him a total of four times before I wrote him off Tuesday May 3rd. The first time, I realized how many red flags there were going in, but still had my fun. Then encounters two through four were a downward spiral, but I guess that is expected when there are so many red flags. This is part one of a three part post for Tampa Boy Encounters #2-4.

Tampa Boy Encounter #2

I never expected to see him again, but two days after my first encounter with Tampa Boy, he texted to tell me he had more fun than expected and that he wanted to see me again. The texts were light, flirty, and a little dirty. He kept telling me how much it turned him on to tie me up and he wanted more. He was basically begging me to come to his hotel that night, but alas, I am a busy girl and wasn’t about to drop what I was doing for a boy. That was Tuesday, I told him I could hang out with him Thursday when I get out of work around 10pm.

Thursday came around and he texted me to make sure we were still on. I replied with a simple yes. I was busy at work and really couldn’t be bothered. When I got out, I tried to call him to tell him I was leaving work and to see where he wanted to meet up. He didn’t answer. I texted to tell him I was running home to eat before we could hang out. About 40 minutes later, he calls to ask me where I was at and why I didn’t just go to his hotel. I told him I had no clue he wanted me to go to his hotel because we never agreed on that. After some of this banter, he said he was going to come over to my place and would be there in 30 minutes.

Tampa arrived. We went straight to my bar, and I made us each a whiskey coke as he packed a bowl. As I was making our drinks, he plugged his phone in to charge and plugged in the aux cord to my speakers. He explained that the reason it took him so long to call me back was because he had left his phone at his baby mama’s place and he had to go get it. Red flag. He continued to say that his phone was blowing up with texts and emails he had to respond to, so he typed away on his phone while I drank my whiskey coke and listened to whatever EDM bullshit he put on. Red flag.

I was basically done with my drink when he finally finished responding to everyone he had to so urgently text back. Red flag. He then sat by me and took a hit. He asked how I’ve been, I started to respond, but hardly got several words out before he started to talk about himself. His ego and cockiness always seem to take control. Red flag.

He then insisted we moved from the bar stools to the couch to be more comfortable, which is obviously code for I want to make a move on you. We sat on the couch, he continued to talk only about himself, I hardly spoke. He never asked me anything and whenever I would respond, he wouldn’t let me really talk much. Red flag.

Once he got over talking about himself, he turned the conversation all into complimenting me, but mostly my appearance and my body. Red flag.  He then made his move, turned towards me, put his arm around me, pulled me in for a kiss. Fuck! I forgot how good of a kisser he was. All that bullshit and red flags ignored once again. We started making out, he then pulled me closer and I straddled him. The make-out session got more and more intense. He started to kiss my neck and moved his hands up my thighs, grabbing my ass, then moved one hand up to my tits. As hot as it was, I stopped him, “I have roommates that can walk in at any moment.”

“So” he said as he continued to kiss me.

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Moments after that, one of my roommates walked in and was startled, “Oh my god!” He scoffed, then turned around and walked as quickly away in the other direction as possible. I got off Tampa and chased after Henry and told him to chill, nothing was going on, we were just making out. He said he was fine, just caught off guard. I felt bad though because he had just moved in like a month ago.

Once I reassured Henry, I went back to Tampa. He then insisted we moved to my bedroom. I laughed and said he couldn’t go into my bedroom because it was currently a disaster. He then explained we couldn’t go back to his hotel because his assistant was there watching his son. Red flag.

“You’re in town for business, you only see your son when you are in town, go be with your son.” I told him.

“He’s sleeping though,” Ryan said.

I kissed him one last time and told him to leave. He left and not even 15 minutes later called me to ask what I was doing. I told him I was in bed. He asked if I was using my vibrator and thinking about him. I laughed and told him no. I was nodding off, he kept talking. After several minutes of him talking at me as I spaced out from being high, he finally said goodnight and that he would text me tomorrow.

He planted the seed. I grabbed my vibrator but did not think about him once.

Yours Truly,
Kallie Pygus

 

Red Flags Equal Fun

Brace yourself, this is a long post, but there are juicy details, I promise. 😉

It has been almost a month since I declared my boy break and I was doing so good… that is until a couple days ago.

I was bartending Sunday afternoon. Usual touristy downtown Chicago wealthy crowd. A tall, tan, blonde, muscular guy walks in wearing a tight gray t-shirt, a rolex, and some nice shades. He sits at the opposite end of the bar from me, so my coworker took his order. As he takes off his shades, he looks right at me and we made eye contact for several seconds. His piercing blue eyes and his kind smile are what drew me to him.

He stayed put on that side of the bar, I could have gone over to check on him, but I decided not to. It was almost 3:30pm, my shift was about to end, I was closing up tabs, I had plans at 5:00pm, I had no time to chit-chat. I wrapped up and as I left, gave him one more look as I walked past him.

When I got out of the bar, I stopped right out front for a minute to find my car key. While I was searching my purse he walked out. As I heard the door behind me, I knew it was him. I didn’t turn around, I found my key, then paused. He then said, “Hey, I’m Ryan.”

“I’m Kallie.” I responded as I turned around.

“Do you know where there’s an open head shop near by? I have all this bud but nothing to smoke it out of.” Ryan asked.

I laughed, “You’re in the wrong part of the city to buy a piece.”

“Where do I need to go?”

“There’s like five head shops all in a row on Clark and Belmont. It’s on my way home, I could drop you off if you’d like.”

He agreed and thanked me for the generous offer. I didn’t know anything about him, but there was something about him that lured me in and I wanted to figure it out. During the 15 minute ride to Lakeview, we did the usual introductions; I found out he’s from Tampa, he’s in Chicago for business but has been here almost all month and is probably going to be here frequently moving forward, he is 33 years old, he is an entrepreneur and is starting a new business venture. Although he was nice, funny, tall and had the muscular build I usually fall for, he was cocky and very much into himself. The majority of our discussion lead back to how much money he makes and he even brought up all the women that fall for him.

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Aside from his overall friendliness, everything about our conversation were big red flags, but I liked that. As we were talking, I was thinking about ripping his clothes off, but I could tell that there is no way he could be more than a good lay.

Right before we got to the head shop, he realized his friend lived near by so he asked if I could give him a ride. I agreed. We went in, he purchased a piece then we left. When I took him to his friend’s place, he asked if I wanted to come in to smoke a bowl and chill for a bit. I explained I couldn’t because I have dinner plans with friends at 5pm. He asked for my number so we can hang out later, I hesitated because of all the red flags. He then persisted, “I think you’re cool, you should show me around the city when you’re free.” I then agreed and put my number in his phone.

I drove home and went to get ready to go to my friend’s for dinner. It wasn’t even 30 minutes after I left Ryan and he called me asking when I could come hang out with him at his hotel. I told him I couldn’t that evening because I had plans. He said I could bring my friends, but no way in hell that was going to happen. I laughed and explained that my friends wouldn’t want to do that. He then tried to invite himself to hang out with me and my friends. I told him I wouldn’t let that happen because what if he turns out to be a huge douche; my friend’s would hate me for inviting him. He laughed then said he would call me in a few hours to come over to my friend’s when he was done with his meeting.

While I was at my friend’s place, he texted at around 8:30, I ignored his texts until 10pm when I was headed out. I texted and told him I was about to leave, but I had to give a friend a ride home. He told me he wasn’t in a hurry and had all night. He gave me an address and told me to come pick him up so we could finally smoke. I agreed.

I picked him up from a house on the south side and when I arrived, I asked what he wanted to do. He told me to show him the city, but first we need to go somewhere and smoke a bowl. So I wasn’t smoking and drinking and driving, I told him I had to go to my apartment and park my car. On our way there, we stopped at his hotel so he could drop off his bag. When we arrived to his hotel, he warned me that he has a three-year-old son that wasn’t at the hotel at the moment, but there are toys around. Another red flag. We went up and he changed quickly. We then went to my place, parked my car, climbed up the three flights of stairs, and he packed a bowl as I made us each a whiskey coke. I took him up to my roof to show him the view. He tried putting his arm around me, I turned and rejected his advance. It was too early in the night and I was still contemplating what I felt about the situation.

After we finished our drinks, he ordered a Lyft and I took him to Wicker Park so we could do some bar hopping. It was a Sunday night, so not much going on, but we still made our rounds. At the last bar we stopped at, he stayed out front to smoke a cigarette and he made friends with a guy that goes by Tank. They got talking. I went in, ordered a drink, and hung out with some people I knew.

About 30 minutes went by and he still didn’t come in, so I went back out. Ryan then asked if I wanted to get out of here, I agreed. He called a Lyft and Ryan, Tank, and I got in the car. The plan was to go to Tank’s place to grab something before we went to Ryan’s hotel to smoke and chill some more. On our way to Tank’s, we drove past an adult book store. Ryan put his hand on my leg, leaned over and whispered to me pointing at the store. I laughed, but thought nothing of it.

Once we left Tank’s, all three of us went to Ryan’s hotel and poured ourselves some drinks and smoked another bowl. Ryan took some adderall and offered some to Tank and I. Tank took one and I declined. Another red flag.

The boys wanted to roll a blunt, so we left the hotel after hardly being there and walked over to 711. Tank kept trying to put his arm around me and tried getting in my face because I wasn’t talking to him. He was obviously fucked up and I could hardly understand a word coming out of his mouth. The boys agreed that we should smoke the blunt at Tank’s, but Ryan had to stop by his hotel to grab his weed. The boys couldn’t stick to one place, it was starting to get annoying, but I played along. When we walked back to Ryan’s hotel, Tank stayed downstairs to smoke a cigarette. Ryan and I went up laughing about how fucked up Tank was. When we got up to his hotel room, he shuffled around looking for his bud as I sat on his bed and watched. He then sat next to me and said that Tank could wait. He leaned in and kissed me. After making out for a couple minutes, I stopped him and said we should probably tell Tank to leave. He tried to call Tank, but it went to voicemail. We went downstairs to see if he was there, but he wasn’t. Ryan then asked, “Do you want to go check out that adult book store?”

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I agreed. All of these red flags, it was 4am, and I still agreed. This night so far has been an adventure and I didn’t want it to end quite yet, especially now that he wants to have fun with toys. The draw to fuck him has increased exponentially. He called a Lyft and we went to the adult book store. He told me to pick out whatever I’d like and he’d buy it. I grabbed nipple clamps, a rope, and a vibrator. He grabbed a vibrating cock ring and some sort of herbal sex pills. He ordered a Lyft to his hotel. On the way back, he grabbed my hand and put it on his cock. I caressed his crotch and rubbed him gently, teasing him the whole ride.

As soon as we got back to his hotel room, he went in to kiss me. It started off slow. A nice ease into what was to come. He took off his shirt, I then straddled him and we continued to make out as he unclipped my bra. Now topless on top of him, he started to kiss my neck and worked his way to my nipples. He then flipped me over, he sat on my hips, keeping me put while he grabbed the rope from the nightstand. He held both my wrists above my head and started to wrap the rope around them, and tied the rope to the bed frame. As he tied me, I kissed his chest, he told me to stop so he could focus on me.

His natural dominance had me soaking wet. Now that I was restrained, he had absolute control. He kissed me briefly, then pulled back, slowly working his way from my lips, to my neck, down my stomach, then teased me by running his tongue across the top of my jeans and rubbing his hand along the inside of my thighs. I thrusted my hips, squirming from the anticipation. He grabbed the nipple clamps and circled my nipples with them. My whole body now craving more, I tried to lift my head up to kiss him, but he pushed me back down, then finally pinched my nipples tight with the clamps. The quick sting of pain was followed by a burst of ecstasy. He then ran his tongue down my stomach, pulled my jeans off, leaving me in just my red lace panties.

Spreading my legs and holding them to restrain me more, he gently licked along the edges of the lace. He slid his tongue up and down each side multiple times, then with his teeth, he lifted my panties to one side of my soaking wet pussy. He continued to tease me, licking  closer and closer to my inner labia without quite doing so. As the tension continued to build, I kept trying to push my hips up to get him to finally eat me. He kept pushing my hips down.

It wasn’t until I stopped my squirming that he finally went in for his first taste, taking a mouthful of my inner labia, then he ran his tongue between my lower lips, up and down, barely touching my clit every time he licked upward. I tried to move my hips down so my clit would finally get the attention of his tongue, but he lifted his head away from my vagina and looked up at me. No words were said, but I could tell he was demanding me to stay still so he could get back to work. I took his demand and relaxed my hips. He then went back to business, licking up and down, up and down, then he ran his tongue up above my clit, bumping the top ball of my clitoral hood piercing, driving my clit crazy.

He paused, sat up and reached for the vibrator. I was already worked up and he just kept the ultimate tease going. He turned the vibrator on, running it along my clamped nipples, then buried his face back down under, and started to circle my clit with his tongue. My entire body pulsing with sensation, I succumbed to everything he was doing.

He ran the vibrator down from my nipples, and towards my clit working his tongue down to my vagina simultaneously. He kept a good pace, switching from using the vibrator on my clit and in my vagina while licking me simultaneously. After several times of changing it up, my breathing got heavy, my body tensed up, I let out a quiet, “oh my god” as my vagina started to contract, my hips pushed up into his face for a good 15 seconds of pure bliss. As I came down from the orgasm, he pulled his face away, a long string of fluids dripped from his face down to my vagina.

As he unclamped my nipples, he asked, “How was that?”

I smiled and said, “That was fucking amazing. I rarely cum the first time I’m with a guy and you somehow figured out all my hot spots.”

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He kept me tied, then stuck his throbbing hard cock in my mouth and he proceeded to eat me out. I took him in deep, in and out of my mouth, running my tongue over the tip of his cock. As he continued to tickle my clit, every lick made me jolt; I was still extremely sensitive from my orgasm. He then pulled his cock out of my mouth, repositioning himself so we were face to face. He kissed me and thrusted his cock inside my soaking vagina. Every thrust he would pull back and pause with just the tip in me. I would try to push my hips up and wrap my legs around him so I would pull him deep inside of me. He kept pushing me down so he could continue to tease me with just the tip of his dick. After a couple minutes of this, he untied me. I was free to do whatever I’d like. I wrapped my arms around him, moving my hips in a circular motion as he thrusted. He flipped us over. Now on top, I was in charge.

I returned the tease favor, by slowing down, pulling him out, running my fingers along his cock and kissing him, then worked my way down slowly, biting his nipples gently. He rubbed my back with almost a downward motion, trying to get me closer to his penis. I slowly licked down the center of his abs to the base of his cock, flicked the tip with my tongue, but then neglected it and licked along his pelvis towards the base of his shaft, but never quite licking his dick. He tried to grab my hair to control me, to push my head to his dick, I pushed his hands down to his side.

Once he stopped trying to fight me, I ran my tongue from his hips and then lightly tickled his balls with my tongue and slightly took them into my mouth. I then ran my tongue up his shaft and to finally take his dick in my mouth, just the tip to start. Sucking lightly, I licked the rim of his head, running my tongue around it slowly. I looked up at him, I could tell he wanted me to take him all the way in. I paused on his tip while we made several seconds of intense eye contact. To break this, he pushed his hips up and I proceeded to move my mouth down his shaft, then added my hand in a twisting motion up and down as I blew him, cradling his balls. Up and down, taking him in a little more every time. Finally, I let his dick slide all the way in my mouth, deep throating him, and I held it while running my tongue along the under side of his dick.

“Don’t make me cum yet!” He said as he stopped me from blowing him. “I still have to fuck you silly.”

He then grabbed the vibrating cock ring and demanded I get on my hands and knees. He stuck his dick in my pussy, I pushed my hips against him, the vibrator tickled my clit with every thrust inward. He kept trying to slow down to prevent himself from cumming, but I insisted he didn’t stop. He then began to thrust harder and harder, until he came.

As he took off the condom, he stated, “Damn! I haven’t fucked like that in years.”

I smiled and kissed him. His phone alarm went off, he looked at the clock and realized it was 8am. We have been going at it for over three hours and he was supposed to be waking up for work at that very moment. He turned it off and we passed out until noon.

When we woke up, he showered and got ready as I just laid there. Once he was out of the shower, we both got dressed. I kissed him and said my goodbye. He then said, “I’ll see you around.”

I laughed and said, “I’m not counting on it. You live in Tampa.”

He said, “We’ll figure it out.”

I laughed again and walked out. I will probably never hear from him again, and that’s ok with me. I wasn’t looking for a relationship to form. All those red flags were just green flags to have a single night of fun with a guy I wasn’t ever planning on seeing again.

My take away, a night of casual fun, no strings attached, is now allowed during this break. The break from boys is more of an emotional break than anything else. I still crave sex. I just need to eliminate the time wasted on guys when I get attached emotionally. Tampa boy was a perfect slip up from this break.

Yours Truly,
Kallie Pygus

EDIT::: I wrote this last night and didn’t post it because I needed to edit it still, but he texted me today wanting to see me again. All the red flags are still there, and he is still not my type based on his ego, but the sex was fucking awesome. We will see what happens.