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

The Tale of Pigeon Bitch

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Yours Truly,
Kallie Pygus