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.
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?”
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.”
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.
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.