Random Encounter

It was my birthday I just turned 30. I was with 2 colleagues at the mall on our lunch break. We were sitting at Starbucks and joking around. We are all straight dudes working at an IT company, but we love to joke around about gay sex. Usually, we joke around with our older colleague, teasing him that he likes to suck dick and so on. Today we were louder than usual. Since today was my birthday I was asking them where they want to eat, my treat, but from one joke to another I told my older colleague that he will be happy only if he can get some cum. I don’t know why but I told him, I will ask around the coffeehouse if any guys want to fuck him, my treat again. I guess I said it too loud since people started to give us nasty looks. I took the joke further and said to him if he doesn’t like the guys I can ask if a girl will fuck him, I will even buy her a strap-on if he doesn’t already have one. I kept teasing and pushing him for a few more minutes. When we decided where we are going to go and were getting ready to leave a really beautiful girl showed up. She was a tall, big ass, big boobs, long hair wearing sunglasses, with huge red lips.

“Hey guys, I heard your conversation and if you are still looking for someone to fuck you, I’m available.” – said the girl, and then left a business card with her phone number on it.

“Just call me and let me know where.” – she continued, pulling her dress up.

Under the dress, you could right away see her white panties, and the massive dick they were trying and failing to hold. She then pulled her dress down and left just like that. We were stunned by what we just saw. Moments later we got up and left. I pick up our cups to throw them away and quickly grabbed the card with her number on it before my friend’s notice. I told them I threw it away with the rest of the trash.

Little about me, I’m not hot. I didn’t have a girlfriend I was overweight, with a big ass. I only had sex 3 times before and it was nothing special, and it was hard for me to find a girlfriend since most of the guys out there are jacked, and I was just a shy fat kid, well man since I’m over 30 now. However I had spent the last year trying to reform myself, train, lose weight, and so on, mainly because I was horny all the time. I don’t consider myself gay, but for the past 5 years since I started to live alone, I have spent a ton of money on sex toys, including a lot of but plugs dildos, and so on. At first, I just wanted to try what it feels like, but the more I used my toys the more I craved a real dick in my ass.

Back to the story. It was a week after my birthday, I was still holding onto the phone number. Maybe due to the promise I made to myself to try new things from now on or the fact that I could not get the picture of that dick out of my head, but I wanted to call that number so bad. I was afraid someone will find out about it, or that I will chicken out before someone even picks up. It was Tuesday night, I was out with my colleagues, and we had a few drinks when I got home a kept drinking for a while alone. I would say that I was the perfect amount of drunk to do something stupid but still remember it the next day. It was around 2 a.m. and I dialed the phone number. The name on the business card was Anabel, so I started to ring, and not long after someone picked up.

“Hello.”

“Um, hello I’m calling for Anabel.”

“Yes on the phone, what do you want?”

“Um sorry to bother you, we met last week, at Starbucks, and you gave me your business card.”

“Last week I don’t remember.”

“We were three joking about sex, you left us your card before flashing us.”

“Ooo, I remember the 3 dudes that were seeking someone to fuck them, which one are you?” – she asked.

“The fat one.” – I replied not knowing what else to say.

“Good I like large men, they have juice asses. Do you want to meet up, my offer still stands?”

“Yea I would like to if you are still willing.”

“Yeap, I’m free Friday night, text me your address and I will be there.”

After that, she just hangs up the phone and that was it. I had a sex date to say. I was wondering if I should rent a hotel room, but I was scared to get caught outside with her so I texted her my address right away and that was it.

Friday came so fast, I took the day off work to prepare, shave my dick and ass, clean my ass, and so on. It was around 19 o’clock when my phone was right. It was Anabel, she said she is here, I let her inside the building told her the floor, and waited at the door. A minute later there she was, again with sunglasses and a dress on, with high heels. I invited her inside and offered her a drink, but she didn’t want any. She walked right into the living room and sat on the couch.

“So do you often pick up strangers at the coffee to fuck you?” – she asked.

“No actually you are my first.”

“Ok” – she said surprised. “Have you ever been with a transwoman before?”

“Actually I have only been with a few girls before.”

“Wait you have never had your ass fucked before? I’m going to be you first?”

“Um, yes.”

“Wow, ok sweaty I promise I will try to be gentle then.”

“Do you do this often?” – I asked her.

“As often as I want to, I’m not ashamed of who I am or what I like.”

“Cool, cool, and do guys fuck you as well?”

“Look honey this is not what this is, I’m here to fuck you, not the other way around.”

“Oh no I get it, I’m just asking.”

“Well, to be honest, it depends on the guy’s dick, I can’t take a big dick up my ass. I like guys with small dick that I can fucked their brains out and from time to time I want them to fuck me too. Now enough chit chat I came here for a reason, turn around, and let’s see that juicy ass.”

I was shaking I didn’t know what will happen or if I would like it or not, but I did as I was told. I removed my shirt and turned my back toward her, dropping my pants and boxer at the same time, exposing my naked ass to her. Shaking it a bit before turning around. She had one of her legs up on the couch and was holding her 7-inch dick in hand stroking it slowly. She told me to not waste time and drop down, which I did before started to play with her dick. I was stroking it, exploring every inch with my hand before she grabbed my head and forced it down my throat. She started to fuck my mouth aggressively, and it didn’t take long for me to gang on that massive cock. But she would pull it out for me to take a breath and then just shove it back in. She stood in front of me and fucked my face for at least 15 minutes before she sat back down on the couch. This time with no instruction I just slid forward a bit and kept playing with her cock. I liked the way her dick felt in my mouth, I liked the sweet taste of it and I wanted more. She was just watching me and caressing my face and head while I was down there sucking on the cock. I played with it for a little longer before she instructed me to lie on my back. I laid on the couch on my back as instructed and then she got down on her knees in front of me and started to play with my balls. She licked my balls, played with my little not even 5-inch cock, and sucked me till I got hard, not that that took long, before telling me to lift my legs and started to lick my asshole. Good thing I shaved it before. I could feel how wet it was getting, her tongue on my ass, she was playing with my anus, sticking her tongue in and out. It drove me crazy. Not long after I could feel her long nails pocking me, she licked her finger and started to fuck me with it, then 2 then 3. I have to admit my ass is a bit loose, but I felt pain on the third finger. She then grabbed her purse and pulled out a tube from it, it was lube. She poured a generous amount on me and then a good amount on her dick, before rubbing it in. She placed her cock on my entrance, looked me in the eyes and just said relax before adjusting her cock on my ass and pushing it in. The pain at the first moment was sharp, but since I was horny and hard, and she was still playing with my hard dick with one hand, the pleasure overtook the pain. I didn’t even realize when she managed to stick it inside. I could just feel it feeling me in. Then she leaned toward me and we started to make out, with her cock balls deep inside my ass. We made out for 2-3 minutes before it started to feel her pulling out, I still had her tongue in my mouth so I could not scream, when she rammed it back in, pulling it out almost all the way, before ramming it back inside. When I started to relax, and my hand grabbed her ass, she took that as an invitation to speed up. She was leaning over me and I could feel her speeding up, you could hear the sound of her balls slapping my ass with every thrust she made. At some point, the speed was so fast that sound got monotonous. I was screaming for the cock, to fuck me harder. She was telling me how great my ass feels, and how tight I am, and she was slapping my ass in the meantime. She was holding one of my legs up and supporting herself with the other while jamming that cock in and out of me. She told me I’m her slut and that she wants to cum on my face. I didn’t care I agreed I wanted to taste that cum. But with the heat of the moment and the speed and force she was fucking me she didn’t manage to pull her dick out in time. So she slammed it in and collapsed on top of me, filling my ass with her cum. That fresh, farm cum hit my walls, filling me up inside, before the warm feeling of it dripping out of my ass. She then stepped over me and gave me her dick to clean it up. The rest of her cum covered the dick she just pulled out of my ass. I licked it all, sucked every last drop of it, I needed more. I told her I want more. I pushed her head down and told her to lick it out of my ass hole, and when she did I pulled her and kissed her passionately. We were swapping the cum from one mouth to another before I swallowed everything that remained.

She lay next to me on the couch and we started to talk, while I was still playing with her boobs. I was starting to get hard again. And while she was telling me about this skinny guy she fucked, and how she preferred juicier asses, I started to pinch her nipples and lick them. Then I moved my left hand between her tights, playing with her balls, before moving down in the search of her ass. I felt that she liked that since she stopped talking and was playing with her other boob. It didn’t take long for me to turn her on her belly, grabbed the bottle of lube which I squeezed on her ass, and started to rub my cock on the ass to lube it up as well. I was rubbing her asshole with my dick, but then she reached back, adjusted her hole to my dick, and told me to fuck her. My dick went inside with no problem at all, and I was laying on top of her fucking her ass before she stood up on all fours and was fucking her ass doggy style. It didn’t take too long for me to fill her ass up with my cum. I right away started to lick off her ass, of course, didn’t want to waste any of it. Shen then turned around and kissed me taking the cum out of my mouth and swallowing it, before leaning down and juicing my dick of what was left on it.

We collapsed on the couch breathing heavily and tired of our little adventure. She was laying on my cheats legs wrapped around me, I could feel her cock resting on my thigh. That is how we fell asleep. I woke up a few hours later and the sun was just rising. I got up to go to the bathroom and when I came back she was still asleep. Her head was laying on the side, she was laying on her back, and I could see cock resting on her belly. I laid on my stomach next to her and I started to suck her dick. She was getting hard but she didn’t wake up so I kept sucking. At some point, I again looked at her face and now I saw her looking and smiling at me. I smiled back with cock in my mount and kept sucking her cock. She was enjoying the morning blowjob. After a few minutes, I stood up and she asked me why is stopped. But I just took the bottle of lube, put some on my finger, and rubbed it on my asshole. Then put some more and rubbed in on her cock, before sitting on top of it. I was with my back against her, and I was jumping on and off her cock, while playing with my own under me, I’m pretty sure she was just enjoying the show. But when I got tired, I stood up, said on the cock facing her, with my legs up on the couch and I started to kiss her. We were making out and felt her thighs start to move, then I felt her dick sliding slightly out and in. Not long after I started to move as well, and I was riding her. We kept making out while she was fucking me. My dick was hard this time, and it was rubbing again her and my belly. I could feel I would cum soon. But before I got the chance I felt her cock twitching in my ass, and then feeling me once again. This time I didn’t stop, I still jumped on her semi-hard cock, grinding my dick again her belly. Not long after Cumming all over her stomach, boobs, even reaching her neck. Dismounting her right after and went down on my knees, to lick the cum of her cock, and balls. Moving slowly onto her belly, tits, and neck, slowly moving my tongue one after another carefully not to miss or spill any of our combined cum. After picking up every last drop and wanting over her and grabbed her chin, forcing her to open her mouth before I spit all the cum from mine to hers, and then kissed her. We were kissing with cum filled mouths. We could feel the cum on our lips and dropping on the side of our mouths before we picked it up with our finger or just straight licked it up again.

After we had swallowed every last drop there is, she went to the bathroom to wash up, picked up her clothes, and left. Telling them she had a great time and to call her so we can do it all over again. After she left I just collapsed on the cold floor with a sore ass, cum still dripping out of it.