3 Boys, 24 Hours

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Yours Truly,
Kallie Pygus

 

Note to Self: Quit Bad Sex

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Yours Truly,
Kallie Pygus

Tell tale sign…

A few weeks ago, I got a text from Isaac, a guy who I haven’t seen in almost a year. This guy in particular is different than the guys I just fuck. He is the type of guy I would date, but when we first met, the timing was completely wrong. I was in a 6 year relationship that was plummeting. Isaac and I were mere acquaintances for a few months while I was still in my relationship. As soon as I became single, he swooped in to ask me out. More on the backstory later…

Fast forward to a few weeks ago… I got a text from Isaac asking if I still live at my loft because there’s a party (which happened last night) that he got invited to by a friend of his. I told him I still live there and he should definitely come. We texted back and forth, and he invited me to an exhibition he’s part of in a week.

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A week passed, I made an appearance at the exhibition. He was doing a performance piece where he was standing with his back to a wall completely still while making intense eye contact with the other performance artist. While they were making eye contact, two guys built a frame and put up drywall to trap Isaac between the two walls and eventually blocking Isaac’s gaze with the other performer. As I walked in and saw Isaac, I quietly approached but kept my distance. As soon as Isaac noticed me in his peripherals, he broke eye contact with the other artist and looked at me, then back at the other performer. Over the time I was there, he only broke his stare to look at me briefly, but from what I saw, he didn’t break it for anyone else. I had to leave before his performance was over. I shot him a text to tell him how bummed I was I couldn’t stay, but I had to get to my friend’s birthday party.

Fast forward to last night… Now it’s been a couple of weeks since his performance. He never texted me back after his performance. I knew when he originally texted a few weeks earlier, he had said he was coming to my loft for the party on September 9th, but I also haven’t heard from him so I was completely unsure if he was coming last night or not.

My friend Ana was in from NYC, so she came last night with some other friends and we all danced behind the bar drinking way too much as bands played and people flooded the space. I kept my phone in sight on a shelf behind the bar hoping that he would text or something saying he was coming. Every time my phone lit up I checked to see if it was him, but every time it was someone else. My roommates asking for help. Friends saying they were on their way. Even a text from Adam (There’s always a red flag…) inviting me to mimosas. No texts from Isaac.

It was a few hours into the party and no sight of Isaac. At this point I had given up on him coming at all, which was fine, I wasn’t sure if he was coming anyways. Josh (Ana’s boyfriend) and I went to go fill the water jugs for the bar, and when we were in the kitchen, I drunkenly spewed my disappointment in Isaac not coming. Josh grabbed one jug, brought it to the bar as I filled the second, then came to grab the second from me.

Well as we brought the water jug back to the bar, there he was. Isaac showed up after all. I walked up behind him and put my hand on his arm to get his attention. He turned and excitedly said hey and hugged me. We chatted briefly, I told him when he was done with his drink, the next one was on me. I went back to the bar and continued to dance with my girls and serve drinks.

Once that band ended, now between sets, the crowd dispersed to the rest of the space, back stairs, bathroom, and roof. Isaac came to the bar and we chatted some more. He asked me if I’m ever in his neighborhood. I told him not really. He then insisted I should come through sometime. I then told him he should give me a reason and maybe I would. His friends came to the bar, he introduced me to them and he ordered a round of drinks. While we talked, he asked for me to come around to the other side of the bar so we could talk more. I looked at Ana and she gave me the nod that she was ok by herself behind the bar. I walked around to the other side. We all continued to chat, Isaac’s eyes on me the entire time even as his friends and I were talking.

Isaac’s friends asked how we met and how long ago. We both answered saying we met in college, but through a mutual friend. We both acted like we didn’t know the exact instance when we met. I said I think we met through Marcela. Isaac brought up a specific place which we ran into each other after we met; it was this place that he initially tried to ask me out before I broke up with my ex. During this conversation, he kept brushing his hand on my side and giving me this look like he wanted me. I told him that once the last band was done, I could give him a tour of the loft. Although he knew of the space even before I moved in over a year and a half ago, he still hasn’t been there before.

As the next band started and everyone came back to the bar, I needed to get back to helping Ana. Isaac stepped away from the bar and centered himself in front of the stage while his friends still sat at the bar. Ana pointed it out and said that he’s trying to play it cool by putting space between us. I didn’t care, it’s not like we could talk or anything while the music is going and people are lining up to order drinks. Not long before the band ended, Ana, Jackie, and Josh said their goodbyes and headed out.

The band ended. Isaac looked at me, but then him and his friends went up to the roof. I finished up what I was doing at the bar, got my roommate to cover for me, then went up to the roof to find Isaac. He was chatting with his friends. I walked up behind him and lightly grabbed his arm. He gave me a hug, we talked briefly, but then he went back to the conversation with the person to his left. I then started to talk with his roommate. He was asking about how it is working at the space, I then explained I live here and it’s an artist loft. I told him there’s eight bedrooms. He had the usual reaction of not realizing anyone lived there and was impressed. Isaac overheard this and said quietly in my ear, maybe I could get a tour of your bedroom. I laughed, and agreed. Isaac then asked his friends if they were ready to see the rest of the space and asked if I could show them the recording studio.

I took them down and walked them through the space. Living room. Kitchen. Wood shop. Bathrooms. Gallery. Recording studio. Then as I pointed out the doors to the bedrooms, Isaac asked “And which one is yours.” I pointed down the hall, then led all four of them to my room. They were all in awe over the space. We all hung out in my room for a bit, but then his friends caught on. Isaac’s friends filed out one by one until it was just the two of us. He looked at me, pushed the door slightly so it was almost shut, then went in to kiss me. I wanted him bad at this point, I kissed him back passionately and as it heated up I pushed the door all the way shut.

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He then told me to slow down, and he wasn’t looking to shut the door. I laughed, but also felt a bit rejected. We then walked out to his friends. They asked what the plan was. I told them they were welcome to chill, there’s always after hours. They agreed and I made everyone some drinks and they smoked a joint. After the first round, I went to go to the bathroom. When I came back, they were getting ready to leave. Isaac’s roommate said that he definitely wants to come back sometime. I told them the next party is coming up in a week. Isaac gave me a hug and said he’d see me sometime soon.

I get that he probably didn’t stay because he had his friends and roommate with him, but I also felt confused by the end of the night. He kept building this tension by being flirty and brushing his hand up on me… but then that kiss was less than what I wanted and he left me hanging at the end.

Now I eagerly want to text him to let him know I’m glad he came by last night, but I also don’t want to come off desperate, but then again we have a history. It’s one of those tricky situations. Do I wait for him to come to me? Should I text him? I usually don’t care. I let guys come to me, but I have also been the one to text first a fair share of times and it hasn’t mattered. It’s 2016, a woman can text a guy if she wants. Why does dating have to be so complicated? I’m usually not one to stress about it, but with Isaac, because he’s not a guy I just want to fuck, my mind is flooded with all these questions and thoughts.

The tell tale sign of liking someone is when they are all you think about. Fuck.

Yours Truly,
Kallie Pygus

An awkward night…

When I woke up at about 3pm, I saw Adam’s text (see There’s always a red flag…). He texted to say it was nice meeting me and we texted back and forth for a bit that day. The next day, he texted to ask if I was free later in the week for dinner. I agreed. I was excited, yet still unsure about him. I had a really good time, but I could tell he’s way more conservative than I am, that plus the whole living with the ex girlfriend thing was a huge red flag. Other than that though, I had a really good time and it was definitely an unforgettable night of adventures throughout the city.

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On the day we were supposed to meet for dinner, I was almost out of work and I still haven’t heard from him to confirm. I know he’s probably been out of the dating game a while, being that he’s recently single and all, but when a guy doesn’t confirm, I always have the urge to just cancel on them. I let it slide. I texted him around 4pm saying I was going to be working longer than expected and to tell him I would be running late. This would buy me a little extra time to get ready, which I needed, while also being a sly way to confirm that he still wants to get dinner. He responded saying that it was no problem and he’ll see me there.

That evening, I got there right on time, went to the bar of the restaurant and ordered a drink. The bartender took my card and assumed I was opening a tab, which was fine, but you’d think she would ask me before just holding onto my card. I was there a good 5-10 minutes before he finally arrived. He apologized when he got there and then sat next to me at the bar. The bartender came by and asked if he wanted a drink. He mentioned that we were there for dinner, she asked if we wanted to stay at the bar and order or get a table. He said the bar was fine. OK… so he set it up for awkwardness right from the start. Not confirming. Running late. Agreeing to stay at the bar. I know he’s been out of the dating game, but dude, all of that is adding up to make me really annoyed.

He started out with small talk. Nothing too exciting. We chatted, he told me about his EMT training, I told him about work, we drank, hardly looked at the menu. The bartender checked on us a few times before we finally got around to figuring out what we wanted to order. We continued to small talk. Still nothing too exciting. He’s very dry and kind of monotone. I think the newness of him has already worn off and was only made more interesting a few nights earlier because of the amount of alcohol we had consumed.

When the food arrived, we ate, talked, ate. We were there a good three hours before we realized the time and asked for our check. And that is when I remembered the bartender already had my credit card. Adam asked for the check and she had said, “Oh, do you not want it all on your tab?” Adam looked confused, then I explained and then we agreed to split it. She seemed a bit annoyed, but it was kind of her fault for assuming in the first place that everything was going on my card and for even starting a tab without actually asking.

We left the bar. I was tired and tempted to call it a night, but then he asked if I was still up to hang out, I agreed. I was holding onto hope that I would regain that spark from a few nights earlier. We walked. He had no plan of where to walk, we just walked. It was a neighborhood he grew up in, so he told me some childhood stories which were sweet to hear. Once we walked without further plans for about 20 minutes, I told him to turn left. He didn’t know it at the time, but I was leading him to my place.

On our walk, we walked right past a sex toy store. He made a point to say something about how his friend and his friend’s wife are very open about their sex life. I told him I am too and I think that sex is a very natural and healthy thing. He kind of shut up about it. I don’t know if this was a turn on or turn off for him at that point. I think he wasn’t expecting that, plus he seems very reserved and a bit prude from what I can tell thus far.

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As we got closer, I told him I lived a few more blocks down. He called me out, “Is this just a sneaky way to get me to walk you home so you can end the night?”

Although that wasn’t the case, I was tempted to say yes, but then told him, “No, that’s not what I was doing. You obviously didn’t have a plan of where or what to do, so this is my way to be sneaky to get you to come to my roof and have another drink with me.”

He laughed and told me that was smooth of me. We went upstairs. I gave him a tour of the place. We went to the bar, I poured us each a whiskey ginger ale and then we headed to the bar. We looked at the view and chatted briefly. He made his move. We started to make out and within minutes, two of my roommates opened the roof door and walked in on us. I pulled away and laughed, then introduced Adam to my roommates. We all hung out for a bit while they smoked their cigarettes. Once they were done, they went back downstairs and Adam and I went right back into making out.

At this point, things got hot. He started to work his hand all on my body and up to grab my breasts. As he felt me up, he started to kiss down my neck and eventually kissed down to suck on my nipples. I was so worked up at this point, yet still exhausted, yet still unsure and leaning towards a no with him. We continued to feel each other’s bodies and kiss until my roommates came up for yet another cigarette break, but this time, they walked to the other side of the roof away from us.

We stopped making out. I realized the time and said I should probably get going to bed soon. He said he would leave whenever I wanted him out. I looked at the clock, it was about 11:30, I told him midnight would be fine. My roommates didn’t seem to be leaving this time, so Adam and I just kind of hung out awkwardly for a bit longer before I caved and asked if he wanted to go to my room.

He agreed. I then gave him a caveat and said there will be no sex and he’s still leaving at midnight. He laughed and still agreed. We went downstairs and went to my room. We got back to making out. I got on top and straddled him. As we were making out, he started to rub my back, which felt amazing, so I told him to keep doing that. What was a make out session, quickly turned into a soothing back massage and cuddle session which I ended up falling asleep on him as he rubbed my back.

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I woke up around 12:20 and realized what had happened. I saw the time and said I should probably get ready for bed. He put his shoes on and made his way out the door, on his way out, he said we should hang out again soon. I agreed, but wasn’t really that interested anymore. I would have hung out with him again if he tried, but he never did.

This was a month ago. And we went the entire month without talking, that is, until this past Wednesday he invited me to a party for Friday. I told him maybe I could show up later, but I had another party to go to. I ended up not being able to go, but told him we should catch up soon. The ball is in his court. I’m not really going to push hanging out again, but if he hits me up, I probably wouldn’t turn him down.

We’ll see if this goes anywhere… Sometimes you should leave it at one night of romance, this is probably one of those times.

Yours Truly,
Kallie Pygus

 

There’s always a red flag…

July 23rd, it was my friend Jackie’s birthday party. A small group of eight met up before a night of drinking to get dinner. I was a bit out of the circle of people, I recognized some of the people from previous events, but didn’t really know any of them. One guy in particular that I thought I knew, but obviously didn’t was Adam.

At some point in the dinner, I asked Adam, “Weren’t you that guy from two New Year’s Eves ago?”

He was absolutely confused, “No, I wasn’t in Chicago then.”

Jackie butted in, “Who are you thinking of? Was it…” She then started to ramble to list off friends of hers it could have been.

I explained, “Good, glad you aren’t him. He kept staring at my tits the entire night and was a total prick.”

Adam laughed, “Thank god I’m not him then.” He smiled at me, I smiled back. At least I didn’t make a complete fool of myself quite yet. Adam is cute, brown eyes, dark hair, clean-cut, nice build. He is former military and conservative, not quite my type, but I was already captivated by this flirtation we have started. It was still early in the night, so we did some coy looks across the dinner table.

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After dinner, we all made our way downtown to the bar. When we arrived, we were joined by several other people. We took over a pretty large section of the Chicago Athletic Association’s game room. Adam sat and ordered a drink, I went off to the restroom. When I got back, the only seating was the opposite side of the section we took over. I sat down, but it wasn’t long until Adam and I started making flirtatious eye contact.

Once the first round of drinks were consumed, everyone was ready for some games. Several of the people went straight for pool, and a group of us made our way to bocce ball. A game of four on four, girls versus boys. Lo and behold, Adam and I both were playing bocce ball. In between turns, Adam made an effort to talk and flirt with me.

As the night progressed, more and more people joined. Adam tried to get me on my own, he insisted we should order another round of drinks at the bar and check out the other side of the game room to get away. When we got to the bar and ordered our drinks, another friend of mine followed and was trying to catch up with me. I gave her a look like, “Dude, I’m occupied right now.” She quickly caught on and walked away.

We then grabbed our drinks and found somewhere quiet to chat. He was sweet. A bit reserved and quiet, had a cadence you would expect to hear out of an old movie, but this only lured me in more. Not more than 30 minutes later, a friend of mine interrupted to tell me she and a group were headed to Chinatown. While I went and said my goodbyes, Adam got pulled off to play shuffleboard with Jackie and some others.

I drank and watched from the sidelines, Adam and I kept making eyes, so I wasn’t really paying much attention to the game. As the game wrapped up, the birthday girl and the few others that were left took over foosball, Adam and I found a chess board to play. We chatted and played and flirted and I totally kicked his ass. As our game came to an end, Adam’s friend came up and summoned us to the bar to take shots with everyone.

One shot down. “Cheers to Jackie!” Another round was poured, without hesitation, we were all grabbing our second shots. “Happy birthday!” Two shots and four or five drinks in, I was definitely starting to feel it. It was about 1:30am, Jackie was still going strong, so she said we should go to Mindy’s, another Chicago Athletic Association bar on the top floor. We made our way up, everyone ordered drinks and sat at the bar, and I grabbed a water and sat on a couch by the window to chill for a bit.

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I sat there watching the lighting in the distance flicker beyond Millennium Park. Not long into my reminiscing, Adam joined me. We sat in silence for a minute. It was nice. To break the silence, he asked, “How would you feel about walking along the lake once we leave?” I was exhausted and a bit tipsy, but I didn’t want the night with Adam to end quite yet, so I agreed.

An hour or so later, they announced last call. I was ready to leave to walk with Adam, but had to wait to make sure Jackie was ok. She was pretty hammered and was flirting with the bartender. He asked for her number, she gave it and lingered. I had to pull her away, the bartender smiled at Jackie as we left.

We headed out, Adam and I walked together a little behind as the other three remaining souls were a few feet ahead.  His friend was on a mission to get us all to the next bar or somewhere we could keep drinking. Adam looked at me and said, “Let’s ditch them.” I agreed. At the next crosswalk, the three ahead of us walked straight and we bolted right and crossed the street to cut through Millennium Park.

As we approached the park entrance, we were quickly stopped by the guard, “The park closes at 11pm.” We turned and walked along side the park towards the lake instead. We walked up Randolph, I knew all along we were going the wrong way to the lake, but I let Adam lead. He eventually realized we were on an upper level street. There was no way to the lake, at least an easy route from where we were at. He asked, “How adventurous are you?” I laughed, although I was in a dress and flats, I am still always up for an adventure. We hopped a few fences, and found our way to Lower Wacker, then to the river walk. Finally, a clear route to the lake.

We walked and talked and laughed and flirted. He’s very well mannered while I have a sailor’s mouth, a weird mix to say the least. I called him out and said to loosen up, he said it just takes getting to know him before he fully unleashes reveals that he is just as vulgar as me. I don’t know if I fully believe this.

The river walk merged into the pier and docks just East of Randolph. We walked along the pier and found our way to the end, the last dock was several police patrol boats, then there was a cement barrier separating the docks and the lake. We faced more fences. Adam asked, “Are you still feeling adventurous?”

“Bring it on.” I replied. He swung his leg around the fence, lifted himself above the water, and reached his leg to the cement ledge. I followed, but being shorter, plus in a dress, this fence proved to be a little more difficult than the ones from earlier. I quickly realized the way my dress was stretching over the side of the fence, it was making it difficult for me to spread my legs far enough to reach to the cement barrier. Adam saw my struggle, and reached his hand out to pull me over.

We continued our journey along the cement barrier. As we walked further and further, suddenly swarms of seagulls flew up above us cawing. It was actually quite beautiful, hundreds of white birds flying overhead alongside skyscrapers on one side, the lake on the other. We approached the end of the barrier and leaned against the wall. Adam created a story about a military man and the lighthouse in the distance. His voice was soothing and somehow blocked out the noise of the seagulls.

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As his story came to an end, he looked me in the eye, I smiled. He smiled back. My heart started to race a little, he leaned in and kissed me. We locked lips, his hands on my waste, my arms wrapped around his neck. A perfect romantic moment you’d expect to see in the movies. We continued to make out for several minutes. He pulled back, smiled at me, and I smiled back. We were quiet, but it was a comfortable silence.

“Do you want to go to the beach?” he asked to break the silence.

I agreed, but then I added, “First, I need to pee.”

He laughed and led the way back to the pier, helping me back around the fence. We walked back to the start of the pier and luckily there were bathrooms that were somehow still open at 4:30am. I went in to pee, he stayed out and waited. When I came out, he asked if I wanted something to drink. I laughed, “Sure?” confused as to where he would get us drinks. Turns out not only were the bathrooms left unlocked, the patio by the bathroom, although gated off, wasn’t too hard to squeeze past the gate and get to the fridges which were also unlocked.

He grabbed us each a sprite, then we found our way to the nearest street to call an Uber. He pulled me in and held me and kissed me and we waited for our ride to the beach. We got in the car, headed north, and were dropped off near the beach entrance. The entrance was blocked off, another place that closes at 11pm. We started walking down Montrose away from the beach, and he said, “Well that was kind of a fail; where would you like to go.”

He had told me earlier that he lived near Montrose Beach, so I said, “We could go to your place.”

Adam hesitated, then revealed, “I would say yes, but I actually still live with my ex girlfriend. We’ve been broken up for two months, I’m the one on the lease, she’s refused to move out, and I wasn’t putting up a fight. My lease ends at the end of the month, so I’m moving out next week.” Red flag… but there’s always some of those.

Not really sure if I should end the night, but still kind of tempted to keep going, I brushed if off and said “That’s gotta  be tough.” I paused, “Well, we can still go back to the beach, just not use the main entrance.”

We walked back, but headed south away from the entrance and cut through the trees and grass. As we scurried through, Adam grabbed my hand as to guide me through faster. As we exited the tree covered area, we slowed down the pace and continued to hold hands as we walked. We ended up on a hill. At the top, Adam pulled me in yet again. He’s very affectionate, which I usually like, but I felt a little off with all of this. He seems way to proper for my taste, but it was still very sweet so I went along.

After a prolonged embrace on the hill, I pulled away and started to head towards the beach. He followed. When we got to the beach, we sat on the ledge just before the sand. He put his arm around me, I leaned up against him, putting my head on his shoulder, watching the waves flow in and out before us. We chatted some, but the night had us both exhausted so we mostly sat in silence, taking in the view in front of us. An hour passed and we watched the sun rise.

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As daylight got brighter, I was quickly reminded of what time it was. I told him I should probably go home. We walked back towards Montrose, I called an Uber home. He waited with me and held me and kissed me some more. I was torn. At this point I was a little turned off by the fact that he lives with his ex still, but I enchanted by his affection. It seems like even the most well mannered boys still have at least one red flag, and this was a big one. My Uber pulled up, we said our goodbyes, and I headed home. As soon as I got home, I went straight to my bed and passed out until 3pm.

I woke up to a text from Adam. Now what to do with it?

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

 

 

Tinder Douche

As I told you already, I redownloaded Tinder again briefly Thursday, July 7. It was about 9:30pm. Well within a half hour, I had a dozen matches, and several messages. One guy in particular held pretty good conversation, at least played along with my banter. I tend to dissect what people say and twist their words in a playful manner to start a flirtatious argument.

For the sake of this blog, he doesn’t need a name. He was a blip in my sexual life, so this guy will only be known as Tinder Douche. Well Tinder Douche started out fun and light via messaging. At one point, he said he’s not looking to date, so I jokingly told him, “I completely understand, I’m on here for strictly platonic friends too.” He was terrible on his defense, and said “No, I’m just not looking to date, but I also don’t want a one night stand.” So basically, he was passive aggressively trying to see if I would be down for a casual sex/fuck buddy type thing. I responded with, “Are you sure you aren’t telling me you aren’t looking for a one night stand so I let my guard down and fuck you the first time we meet? I’ve got my eye on you.”

I thought it was funny how hard he tried to say he wasn’t looking for a one night stand, but he also wouldn’t admit to wanting a fuck buddy, but also said he didn’t want to date. He was getting so worked up every time I twisted what he said. He eventually ended it with, “I like your style. You can really talk some shit.” Our flirtatious messaging went on until about 11:15pm when he messaged saying “Instead of messaging for the entire hour, we could have met up.” I shot it back at him, “Well isn’t it past your bedtime?” He quickly responded to tell me he could stay up till 3am tonight. I agreed to meet up with him for drinks at a bar near me. I told him to text when he got close.

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He texted when he was parking. I walked down and saw him by his car. We went into the bar, he ordered a beer and I got my usual, Jameson Mule. He seemed nice, a little bit bro-y, but not too much to send me running out the door. Aside from being nice with a dash of bro, nothing really stood out to me. We were at the bar for a little over an hour when they started last call.

Tinder Douche said he still had two hours before he needed to go to bed, so he’s open to going somewhere else. Being that I lived a few buildings over, I offered my place because I have a bar and rooftop. He declined because he didn’t want any chance of my roommates being around. He then offered his place and promised he would give me a ride home at 3am. I agreed and we drove to his.

We went to his kitchen, he poured us each a drink and we continued to talk. I noticed right away that his kitchen wasn’t your typical 24-year-old boys’ kitchen. It was pretty clean. The entire apartment was clean. He also told me how he knows how to cook. I was impressed.

Although he wasn’t my type romantically (he’s a bit too white suburban bro), he was still cute, nice, and had some redeeming qualities. At the moment, I was intrigued. I could see him being a good lay, but I’m unsure of how far I would take it or how long he’d be in the picture because he definitely isn’t my type.

After we both finished our drinks, he suggested that we could watch a movie or something in his room. I laughed, no one really watches a movie when they’re hanging out with a guy from Tinder. They don’t call it Netflix and chill because people actually watch movies. I was hesitant, but intrigued enough, so I agreed.

We went to his room and sat on his bed. He started scrolling through the TV guide and found a movie on HBO. We sat back, talked briefly, but he went quickly in to kiss me. His kisses were surprisingly full for a guy with thin lips, but being that his lips weren’t the fullest and his facial hair was well past a 5 o’clock shadow, it was nearly like having sandpaper rubbing against my face. Not fun. I pulled back and told him to be careful, he got the picture and kissed me lighter.

As things picked up, it got a bit more hot and heavy. He kissed down my neck and unzipped my jeans, pulling them off as he continued to kiss me. He then lifted my shirt off and unclipped my bra. He was pretty slick with his maneuvers, I’ll give him that. He reached down with his hand, and massaged my clit. I was in clit tease heaven at this point. Not many guys can get the right pressure on my clit that quick, but he managed to do so.

Prior to this, there had been no discussion of our kinks or desires. He either had the exact same sex style as me, or he knew exactly how to read my body as I reacted to whatever he was doing. He nailed the pressure on my clit. Then he went in to my nipples, started gently  rubbing them with his fingers, then built up the pressure into some squeezing and pinching, then went in and bit my nipples. I never told him I like my nipples bit, but he figured it out anyways. It was hot.

Soon enough, his magic on my clit and nipples had me worked up. He had me soaking wet. He knew I couldn’t resist at this point, he looked at me wanting me to want him. I paused, I was so turned on at this point, so fuck it. I told him to grab a condom and we fucked hard. I wasn’t expecting him to pull my hair the way I liked it, or to pin me down and restrain me, or to rub my clit or bite my nipples the way he did as we fucked…. but he did it pretty damn well. Some guys just fuck me the way I want it; he surprised me, nothing stood out earlier in the night, but he sure can fuck.

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He came. I didn’t. He got me so close to cumming, but alas, something about the first time rarely gets me there. I have a wall up that has to be penetrated before I trust a guy to show him how vulnerable I can be and unleash my orgasm. As we laid there naked for a few minutes, I saw the time. 3:20am. I told him it was past his bedtime and he should give me a ride home.

Once he dropped me off, I walked up my four flights of stairs, got ready for bed, and passed the fuck out. He was fun, if only I kept it at just one night, he might have not gotten the name Tinder Douche.

Yours Truly,
Kallie Pygus