I was asked about my “hoe phase” recently and realized that I never really had one. However, I had a very slutty weekend in the beginning of the summer a couple of years ago. I knew that I was off from Saturday morning until Monday morning and only had plans with friends on Saturday afternoon, so I wanted to pack in a date and sex filled weekend. There were three first dates between Saturday evening and Sunday night, followed by spending the night at a FWB of mine nearby. Obviously the optimal option for a fun, sex filled weekend is to go on a trip somewhere with one person, but she was out of town and I wasn’t comfortable enough with anyone else to plan such a trip. So I was left with hitting the dating apps and hoping to share enough of a spark with someone to cancel any other plans (spoiler alert: it didn’t happen.)

Wednesday morning I had made accounts on the two most common apps, posted my best pics, and wrote something along the lines of "let’s do your dream local date this weekend.” I had a lot of matches with girls who wanted five star meals or shopping excursions so I guess it gave off a bit of a SD vibe, but eventually I found three attractive women who had more reasonable ideas. It happened to work out that I was able to book all three of them without overlap, one in my borough of New York on Saturday night, and two on Sunday in Manhattan. Parts of it were a blur, but I will retell this story to the best of my ability. Enjoy!

Saturday- Deb After I hung out with friends, I prepared to meet Deb. Deb was tall, thick, blonde and blue, sweet, and very easy going. She wanted to drive to the water, chill and chat, while drinking and eating the good gummies. It was going to be a cute hookup and chill, so I asked a friend of mine for his candy stash and bought some Trulys before heading over to meet her. She was so shy in real life, and I was shocked at how different she was from our prior communication where she was outgoing and almost bubbly over text. Nevertheless, she warmed up pretty quickly (I’m sure the stuff I brought helped) and was soon pressed up against me giggling into my ear and lightly teasing the bulge in my pants. Soon we were making out with reckless abandon, and she actually brought my hand up to her boobs.

She wanted more, but unfortunately it was already late and she was working early the next day. So we went back to her car and to kiss goodbye when she asked me if I wanted a blowjob for the road. I wasn’t going to turn that down and the kisses on her neck turned into us piling into her tiny car and yanking my pants off. Deb’s blowjob skills were superb and she somehow managed to navigate the cramped quarters and suck my dick like a pro. My legs were splayed out at 90 degree angle, one on the dashboard and one behind her body as she caressed my balls and gagged on my cock. She was pressed up like an accordion but was a real trooper and only stopped to assure me she was comfortable and enjoying herself. Her finger teased under my balls but she felt me yank her hair and laughed before cupping my balls again.

I was ready to cum and Deb was ready to swallow, literally begging for my cum as the head of my cock stayed in her mouth and she jacked me off with her spit covered hand. I yanked her hair and subconsciously thrusted my hips, forcing my cock to go further into her mouth and shooting my cum down her throat while she moaned and sent the most pleasurable vibrations up and down my shaft. I looked at the clock- 17 minutes a pretty long time to be choking on a cock while folded in half in your tiny car, and thanked her profusely for all of her efforts. Deb laughed and told me she’s more of a “slap my ass on the way out” gal and rolled over to stretch her legs over me and giving me unfettered access to her juicy ass.

“No marks please, Daddy” was all she said before feeling the palm of my hand slap against her denim shorts. I gave her a few solid spanks and enjoyed kneading her thick ass cheeks under the denim but she needed to go. I quickly slid my hand against her muff and felt the warmth of her arousal before reluctantly sliding her legs off of me and opening the door to exit the car. In the darkness of a quiet night, I stood up and then pulled up my pants before watching Deb get comfortable in the drivers seat and rolling down her window for me to go around and kiss her goodbye. I kissed her passionately while leaning through her opened window and asked if she wanted to hang out again, perhaps I could return the favor for her. Deb just looked up at me wistfully and showed me the lock screen to her phone, which was her showing off a sparkling ring finger with a man smiling happily beside her. “I wish” was all she said before putting the car into drive.

Sunday Morning- Aurora
I had fallen asleep right away the night before and got up at 9, still thinking about how I was sucked dry the night before by a naughty engaged woman. But I soon threw on a polo shirt and chinos before taking the subway to midtown Manhattan, I had two dates planned, one at noon and one at 6 which hopefully meant time to grab a quick bite myself in between. I was meeting Aurora in a cafe and we were going to grab food to go before finding a park and day drinking whatever whatever she had in her fridge (which turned to be half a bottle of rosé and some assorted cocktails in a can.) I knew she, like every other NYC college student, had roommates and hoped that we would be able to get away with some sneaky public fun.

We met outside of the cafe and hugged before ordering some food and heading over to a relatively quiet park that she was familiar with. Aurora was the stereotypical leftist college student in NYC: petite with long dark hair and blue eyes, skinny, and had a few random assorted tattoos and piercings. She was wearing a white tee which was tight enough to accentuate her b cups and pierced nipples, with long enough sleeves that I could barely catch a glimpse of her dark and thick underarm hair through the thin white material when she lifted her arms. A small pair of cotton shorts which showed off plenty of pearly white skin and a little flowery handbag (thrifted of course) completed the look.

We chilled and got a little tipsy too early on a Sunday when the topic of feminism inevitably came up. I am pro gender equality but wouldn’t call myself a male feminist, and thought that it would definitely be a dealbreaker for her. But Aurora had her list of questions to ask and I must’ve passed her test because she climbed onto my lap and nuzzled in close to me before whispering “you would take care of me, wouldn’t you?” Followed by my name and a quick kiss on my ear as punctuation. She was so light, I easily pulled her into my lap to kiss her and taste the faint trace of alcohol still remaining on her lips. Her lips and tongue attacked mine with such passion while my hands ran up and down her tight body, stopping on her little butt to squeeze while we made out.

It happened to be a quiet park and we weren’t too close to anyone so I felt comfortable kissing her soft neck and tasting her sweet skin, it seemed like she had showered just a couple hours earlier. Aurora just purred in my arms and giggled when my hand reached up to cup her little tit, playing with her piercing between my fingers as we made out aggressively. My greedy hands had free rein to her body and made the most of it- pinching her little ass, massaging her lower back, and then reaching up to tease her boobs and hardened nipples. I started cupping my hand over her pussy and shorts, feeling how warm she was in the most sensitive of places when she stopped kissing me and held my hand.

“I just want you to know that I don’t believe in the body grooming standards of today and keep my hair natural” she said proudly and then tilted her head expectantly. It was my move now and she was daring me to make it. “I know, cutie” was all I said before slipping my hand into her shorts and feeling her soft cotton panties “and I want you so bad.” Aurora was shocked but just laughed when I said that her white shirt was advertising her natural armpits and I assumed she kept it natural down below as well. “Guilty as charged, Sir” she said with a laugh “have your way with me.” I checked to make sure we were still in a quiet area, and the slid my hand into her panties, feeling her hard breath out on my neck as my fingers brushed her curly pubic hair on their way to her clit. Her soft pubes were slick with juices around her tight little hole and I pressed two fingers inside before pulling my hand out and making a show of sucking my fingers until she facetiously slapped my hand away from my mouth.

She was in heat, grinding her pussy against my legs, moaning into my ear, and practically yanking my hand back down into her panties. I had flipped her around so that she was sitting on my lap with my hard cock nestled between her butt cheeks and our bags and garbage in front of us, somewhat obstructing the view of my hand in her panties. Aurora twisted her neck so we could continue kissing while I had two fingers buried deep in her pussy, and the palm of my hand was pressing against her clit, with my other hand doing its best to keep her wriggling body in place on my lap. Finally I pulled out and rested my right hand on her soft bush while I played with her clit. I used my two fingers which were soaked with her juices to manipulate her little love button in slow circles while we kissed and I felt her breathing changing in my mouth.

I spread her legs apart a little further before kissing her one last time and then using my left hadn’t to choke her gently as I brought her to orgasm. And that is exactly how Aurora came: with my hand on her neck, choking her slightly and talking dirty in her ear while my fingers went in furious rhythmic circles on her clit. I watched her pretty blue eyes bulge before rolling back in her head and she used both of her small hands to squeeze my forearm while she rode out her orgasm on my lap. By then my hand was thoroughly drenched in her juices and she watched me pull it out, trailing strings on grow from her sweet pussy. This time she didn’t let it go all the way to my mouth and diverted it to her mouth before sensually sucking them clean. She laughed about not willing to share her precious juices that easily and we spent another hour or two just walking around and kissing to round out the afternoon, where we broke for our own suppers, her with her cousin, and me by myself in preparation for the next date.

Sunday Night- Pauly I grabbed a quick bite to eat myself and thought about the karmic circle of orgasms and how much fun it is to just meet a stranger, talk about life, see what you have in common, and then hopefully pick the right time to make a move. I then freshened up (most department stores will offer you a squirt of cologne) and continued to the Upper East Side where I was meeting Pauly, a social worker in her high twenties. Pauly was tall, 5’8 and very tanned with curly dark hair and chocolate brown eyes, with a grabbable ass and cute boobs. Pauly was half white and half Mexicana, so she liked spicy food and spicy sex, but everything else vanilla (her words not mine.) We met in a bar and got more drinks, so I was maintaining my buzz and was a lot more outgoing and chatty than I usually am on a first date. In fact, I met her a couple of times after that and she mentioned that I was more bubbly on that first date than any time since.

We spoke a lot about her industry and psychology in general, which was fun, until the famous experiment of falling in love was mentioned. I highly recommend you look into this- it’s about 30 questions which get increasingly more intimate as they progress, and end with staring silently into each other’s eyes for a few minutes afterwards. Well of course we tried it and asked each other all of the questions while I rubbed her thigh and she caressed my biceps before setting a timer for the staring contest. After it was all set and done I immediately kissed her softly and asked her if she felt anything. Pauly replied in the negative but that she still enjoyed it, and the kiss. I wasn’t feeling smitten either so we decided to go for a walk and continue the kissing part.

We walked back to her apartment which was surprisingly close and although the sun was still setting, she invited me inside “for better light- in case we are going to have another staring contest.” But the way that she was kissing me in the elevator showed me that we weren’t going to be sitting silently staring at each other. As soon as we got in to her room, she hit the dimmer and our clothes started hitting the floor! It was one of those times that everything is just a whirlwind of arousal, and I can’t even tell you the order of our hands and mouths on each other’s body. But next thing I remember, Pauly was standing next to the bed that I was laying facedown on, fully nude with my head between her legs.

It is an interesting position to eat a girl out, but I definitely made the most of it. My hands were clasped on her supple Latina ass, squeezing her cheeks as I stretched my tongue out as far as I could into her sweet cunt. Pauly had a thin landing strip above her kitty and it was tickling my nose while I licked her salty sweetness. Her hands were in my hair and I was trying to breathe and suck her clit at the same time, but unfortunately it wasn’t very easy and I had to tap out from this reverse blowjob. She very much appreciated the effort and told me to stand up so she could show me how it was done. I eagerly listened to her instructions and let her pull down my boxer briefs before marveling at the thickness of my cock.

Pauly teased and kissed my boner while her long nails grazed my balls, until opening up wide and taking most of it into her mouth. She held it there and looked up into my eyes while breathing through her nose and cupping my balls before lifting up her left wrist. She wasn’t wearing a watch but I understood her perfectly and laughed before saying that I wasn’t going to time this staring contest. She just tantalizingly slowly let my cock out of her mouth and said “well if you’ve had enough staring Into my eyes, then its TIME to fuck me doggy” and opened up her dresser drawer to show me a box of condoms. I had my own and went to slide it on while she got on all fours and put her hands on her ass, ready to spread her cheeks for me.

I firmly grasped her thick hips and slid my throbbing erection between her pussy lips, I had been teased all day and needed to pound her tight, warm, little hole until I could release all that sexual frustration. I always find that first gasp when you slide into a woman to be so incredibly sexy, that little half moan half caught breath, and Pauly might have the sexiest one I’ve ever heard. Words don’t do it justice, but it will forever be in my spank memory bank. She wanted it rough and I quickly picked up speed while spreading her cheeks and spitting on her asshole. She knew where my thumb was going next as flexed her asshole around it, making a tight little ring for me to grip. It didn’t take long for Pauly to cum, and I fucked her through the orgasm, bringing myself oh so close as well. Feeling her tight pussy clench up around my penis just about put me over the edge, but I was able to hold off until she caught her breath and sat up.

That’s when I took off the condom and stood over her, my hands roughly in her hair. Without hesitation, she started stroking me and spitting on my cock while looking up at me. Pauly could feel me throbbing in her hand as I tensed up ready to explode and told me “cum on my tits, but stare into my eyes again while you do.” I didn’t need any further instructions and held her hair while my knees went weak in orgasm. I was all pent up and came hard, ropes across her chest while we stared into each other’s eyes and she bit her lip. I don’t know if there is an eye contact kink, but we both enjoyed it that night, because after we cleaned up and cuddled, we had some lotus position sex with heavy eye contact as well before I had to be on my way, work started too early to sleep over by her.

Monday- Eleanor So it was still Sunday night when I got back on the train home and saw that Ellie had texted me an hour earlier to tell me that she was back in town and wanted to get food. I told her that I was heading back from Manhattan and would stop by to pickup her favorite Chinese before coming over. Ellie was a long term FWB of mine on and off who I wrote about earlier (she very quickly got into relationships that lasted anywhere from 3 weeks to 3 months) and when I told her where I was coming from, she laughed and asked how the date was. When I got to her place she quickly ushered me inside before saying “straight to the shower, dirty boy, I don’t wanna know where your hands have been.” When I got out it was only 11 o’clock but we were both tired and decided to watch a movie and cuddle before falling asleep. However the next morning we were both more than ready for action and we both said that we missed this as she slipped down onto her rightful place on my cock. The familiarity was perfect, even though it had been at least a month since we fucked, and we both knew how to hit the right spots for each other. We came together, as we often did and got ready to start our workweek.

Thank you for reading! I hope you enjoyed! And thank you for almost 700 followers!