I’ve told this story more than a few times. Hopefully it’s not familiar to anyone, as being anonymous here is my preferred way of being.
It was a Tuesday night in my mid/early 20s. I worked a shitty tech support job in central Florida that was stressful but mostly comfortable. My friend I moved there with and I would frequent a local bar that catered to the local school students. They also had pitchers for $5 and even then, that was a good deal.
So anyways, my friend and I would get a pitcher or two and sit outside to sort of people watch as this bar was in a plaza and it was frequently busy. That night was quite busy. A line of people going in and out of the bar, and the club next to it made the foot traffic in front of us constant. I spot a redhead, natural might I add – that lighter red that doesn’t come from dye, and she was thicc in all the right places while have a tight narrow waste. Wearing booty shorts and a wife beater with a black bra holding her decent sized tits underneath. She was shorter, around 5’2” but had the best proportions out of anyone I saw that night.
Once the line progressed and it got to where we were, her and her older sister (nowhere near as attractive) started chatting with my friend and I. Asking what we were doing, if we planned to go to the club. I said, “Nope, I plan to stay here and drink a pitcher or two with my boyfriend.”
It got my friend chuckling and she asked, “Oh you’re gay?” I replied with “Absolutely.”
They both got really excited and started hardcore flirting with us. They sort of knew we were joking but the fact we put up a wall of “not being interested” made them want to try harder, and they so did. They hopped out of line, sat with us. Helped us finish the pitcher and even went to get us another. While sitting next to me, I massage her thigh under the table and she keeps talking as if nothing is happening. I kept going higher, and higher as her smile grew and grew. I stopped just short of her crotch and left it at that.
They eventually went into the club which was their original plan. My friend and I still sat at the same table and drank for about another hour before we decided after we finished our drinks we would begin walking home. We were responsible! No drunk driving for us.
Right before we leave, the sisters come out of the club drunk, loud, and laughing. They point to us and scream “THE GAY GUYS!” in unison. Was like nails on a chalkboard haha.
They ran over to us, her sister hugging and sitting by my friend while the redhead grabbed me, kissed me on the neck and sat on my lap. We obviously stayed and chatted for a bit as it was fun. We were young, drunk, and had at all times in the world.
While sitting on my lap she ‘dances’ by just rubbing her ass across my crotch while lightly bouncing up and down. The booty shorts being eaten by her ass. I sure as hell did not complain and I was starting to get hard from it. Anyone would. Once she was done bouncing around she put her weight back down and sat right on my half hard cock. With a glance back and smile I knew she was a fan.
Her sister and my friend even noticed the look and asked “What was that about?” I answered with “Oh I just pinched her butt when she sat back down.”
She was a good girl, and went along with it.
She would push down and move her ass around my lap in small circles, basically rubbing my cock through my pants for me. I look down and pull her booty shorts into her ass a bit more to see her cheeks. I grab both sides and push her cheeks in and out a few times. My hands travelling down the back of her thighs until I was holding both thighs, one in each hand. I decided to play that little game of chicken again. I slowly massaged up her thighs. She’d give a push into my crotch with her ass or moan quietly to me that she is enjoying it. At this point, my half hard cock was as torqued as it was gonna get in those pants.
My hand makes it to just shy of her pussy again and stays there, just massaging her thigh. I have an internal dialogue trying to decide if I should go for it or not. She could flip out, yell at me, slap me, who knows. I then just wondered, isn’t she massaging your cock with her ass right now? Best to return the favor.
I grab the front of her booty shorts with my left hand and pull them away from her right thigh as they were tight, giving me an opening. I didn’t do this quickly, mind you. She could feel it all slowly happening and didn’t make a flinch or effort to stop me. I slid my right hand up first and put a finger right in her pussy. She pushes back hard on my cock, harder than before. This time it was even obvious to my friend and her sister. They both just looked and rolled their eyes, ignorant to the fact I had a finger in her pussy and was working up to two.
She sat talking to her sister and my friend as I slowly go in and out of her tight pussy. Shaved clean and soaking wet from pussy juice and the sweat from the club. I don’t know why, but I discover sweat incredibly hot under the right circumstances. When things started to wind down she suggested both my friend and I drive them home in their car as they were too drunk, that they’d drive us home in the morning. Her sister objected to this, but my friend and I convinced her. So much for not driving drunk.
I get in the driver seat and she gets in the passenger seat. Her sister and my friend in the back. With her own sister in the car, she starts taking off her bootyshorts while I am driving. I look over and it’s bare pussy and ass in my face as she is dancing. Her older sister is raging in the backseat to get her to stop. She eventually settles down but keeps her shorts off. Her hand on top of my pants the entire drive. When we did get back to their place, it was a nice house in a gated community. They definitely came from money. When we all got out, she left a wet spot on the leather seat. Hot. As. Fuck.
We all walk around back to a little concrete patio and drink a little more. The little sister with her bootyshorts back on, unfortunately. The older sister is staring at me with rage. I found it funny. She mentions “Well I guess I’ll just fuck your friend.” thinking it was some kind of attack? And at that moment, her rage was reduced to jealousy as the curtains were pulled back. She went to use the bathroom after a bit and the redhead and I locked eyes and just started going upstairs.
We knew what we were there for. My friend says “Great, leave me with the sour sister.” as we walked out of view.
Her door was at the top of the stairs. She led me in by my hand, taking her bra and wife-beater off the second we get into the room. She had nice tits with light nipples. I discover most redheads have light areolas. Might just be me. We start making out hard. Heavy sounds of saliva and lips and tongues rolling over each other. She pushes her bootyshorts off as we make out and I begin to finger her pussy. I pull 2 fingers out of her pussy and I lick them. I love tasting pussy. She joins in licking her pussy juice off of my fingers and we both giggle a little about it.
She pushes me back on her bed and undoes my belt buckle and my zipper. She pops my cock out of the top of my underwear and says “I thought it felt this big” with a smile.
She starts sucking it immediately after her remark. Swirling her tongue all around my uncut cock and under my skin. I pull her big hips and tight waist over my face, open her legs, and sat her pussy right in my mouth. Perfect height. I swallow so much pussy juice and sweat as I keep sucking her lips, licking her clit, and fingering her pussy. She starts to sit up as she cums and my nose is basically in her ass, and I love it. She is rubbing her pussy and ass all over my face as she moans loudly. As she calms she says my precum tastes good and wants to fuck.
As I’m putting a condom on she is already getting on her back and spreading her legs. She wanted cock in her tight wet redheaded pussy and I wasn’t gonna disappoint. She is licking her fingers and adding spit to her already wet pussy for me. She knew it was gonna be tight. She had the sort of tight pussy only the head goes in at first. You have to work her up to take the rest of the cock, and I did. Slowly pushing it further and further in each stroke as she moaned and whimpered. I have both hands on her throat as I’m basically forcing a big cock in a tight pussy. She shakes her head yes, so I squeeze gently. Her face turning red and eyes rolling back with ecstasy, smiling and wheezing every time.
Hey, I’m not 100% sure why a lot of women like being choked when being fucked, but I oblige.
She cums a few times and needs a break. We lay there and talk a little. She says she is really enjoying tonight, that we need to do it again. She straight out says, “I wish my boyfriend fucked me like this.”
“Uhm excuse me?” I said.
“Oh yeah, I have a boyfriend. He is some chubby guy that doesn’t fuck like you do.”
“It’s a good thing I find that hot.” I said. More smiles from her. For being such a slut, she had a pretty smile.
“Ya know, he wants to try to fuck me another way but can’t.” She said, seemed like a lie, but I went with it. I said “How is that?” She replied with “Oh you know…”
“In your ass?” I ask, as I already fucked her mouth. Another cute smile.
“Who knows, maybe it’s just too tight.” she said with her lying mouth lol. She wanted fucked more but her pussy was sore. I think she wondered maybe I wondered it was gross? Not the case.
She rolls over on top of me and starts kissing me more. I spit in my hand and rub it all over her asshole before putting a finger in, after a few minutes another, and another until I had 3 fingers in her asshole all at once. She held her ass open with one hand the entire time, she wanted this. Her spare hand grabs my cock and starts jerking it off, keeping me hard the whole time. I feel this was something she liked doing. She kept me hard at the bar, the ride home, and of course as we lay naked together too. She tugs at the top of the condom and pulls it off.
“Oh we don’t need that” she says as she throws it across the room.
I push her over off of me, put her on her stomach so her ass and legs were hanging over her bed. She reaches back and pulls her ass open for me while looking back at me smiling. Her ass and pussy were pink and contrasted with her pale skin. She was soaking wet and looked so inviting.
I get behind her as I line the head of my cock up to her asshole and slowly push in. She is moaning, whimpering loudly when I go too fast so I slow down. I spit on my cock every now and then as it slides in and out of her ass. She is nearly dazed with stimulation as I keep pounding her ass.
I pull out to take a short break and lay on my back beside her on her laying on her stomach. At this point we had been going at it for at least an hour. We were out of breath trying to catch it and slow our hearts down. She reaches over and keeps jacking my cock.
“I really want your cum.” she says as she lazily keeps me hard. She gets up, straddles me, and sits on my stomach. I can feel her wet pussy and her stubble poking into the skin of my stomach. I like the feeling a lot.
She lays down on my chest for a few minutes, both still out of it. She looks up at me from my chest after a few minutes with a smile again. She closed one eye as if concentrating. I was confused, until I felt her hand grab my cock again. Jerking it more to get it rock hard again. She slides back leaving a trail of pussy juice on my stomach and lines my cock up with her ass again. This time, she pushes back/slowly sits on it. It felt so fucking good. Her pussy could only take my cock about 3/4 of the way, while her ass took absolutely all of it. This was the first time someone was on top as I fucked their ass. Was a new angle, one I didn’t even knew worked at the time, but oh damn did it work.
We made out as she bounces her ass up and down my cock. Both taking turns spitting and rubbing it on the shaft of my cock as it slides in and out and in and out of her asshole. I’m pulling her hair as she goes down, pulling her down on it even harder. When pushing down hard she rocks back and forth slightly and it felt like her entire ass was squeezing and stroking my cock. I look into her eyes and just say “Yes, that’s the fucking spot.”
She kept her ass pushed hard down and rocked back and forth, staring at me as I choked her, pulled her hair. I even spit in her mouth/on her face when taking turns adding spit to my cock. She was so carnal in every way, it was probably the sexiest fuck I had had in my life until that point. I grabbed both of her tits and use them like handles to rock back and forth. That turns into just me pinching each tit hard, pulling and pushing. Wish I knew about clamps back then 😉 I begin to get close to cumming. I have some stuttered breathing and she notices.
“Yeah?” she said. “Oh fuck yeah.” I said back.
She knew I was about to cum. She rocked back and forth faster and faster squeezing her asshole on my shaft as she did it in pulses. It felt so good I couldn’t hold back anymore. I grab her throat and squeeze as I pump cum deep in her ass. She is squeezing with those pulses as I drain all of my cum into her. After embracing for a bit she fell to my side and we lay there a bit longer. We finally exchanged numbers at that point.
I get dressed and go downstairs. She hangs out for literally 3 more minutes before passing out on her couch. We dipped soon after, with radically different personal experiences to tell about the same night.
I still refer to her as ‘Tuesday Night.’
Reworked for grammar and structure.
HMT, also known colloquially as ‘Tuesday Night,’ you were so much fun.
I left it out of the story, but her terrible sister actually came in the room mid session, followed by my friend. They were unfortunately still dressed.
It was a scene, that went like this.
She breaks into the room, and sees my cock clearly with no condom on it as we both jump up.
“What are you going to do when you get pregnant? Huh? dad is gonna kill you!” her sister says
“There isn’t a risk of her getting pregnant!” I said. She looked confused.
“Why is that? Are you sterile or something?” She said in an insulting tone….she really should have fucked my friend to not be jealous.
I looked at her and she shrugged with a smile, sort of giving me permission to say ” Well because I was fucking her in the ass.”
Her sister’s mouth fell open in shock and she got flustered, and left the room. My friend slowly followed her out, after giving me the thumbs up lmao.
Her sister and my friend never hooked up. He said he just drank more and smoked while I was up there for a couple hours. He said she sort of tried to initiate it but stopped as he was low energy. He wasn’t feeling being a fallback dude.
Also, the next day the redhead texted me, saying that she shit out so much cum that morning and that she enjoyed it. She was a freak