[Group] Craigslist Days Revisited

I relocated to the Tampa Bay area about 12 years ago. The job I had was extremely flexible, I had a LOT of free time on my hands.

My newness to the Tampa Bay area left me curious about the areas notorious adult lifestyle scene.

Craigslist casual encounters was the easiest way to check out the lifestyle.

I would check the adult classifieds daily and usually several times a day. More often than not the ads were fakes or scams. I have several stories of the encounters that were not fakes or scams. This story is of a real event that I was a part of. I don’t mind sharing and I hope you enjoy it!

As I briefly stated, I had a large quantity of free time in my new city. One day I was scrolling through the endless list of fellow lovers of arousing and fun encounters, I click on an add looking for participants in a orgy/ possible gangbang.

I’m interested.

The add was a bit vague. Really a few words and an email address for more details. No pictures. These were the adds that had the possibility of actual realness. Straight to the point.

I email and received one back and hour later. The woman was a mid-fifties divorced MILF who decided to relocate from the southwest to the Tampa Bay area. She moved to the area to try and start a career as an amateur pornstar so to speak. The Tampa Bay area has it’s fair share of amateur porn stars. She was attempting to join the ranks of them.

As requested by the received email, I send pictures and stats. I received several SFW pictures and a short email back soon after. The pictures are good. She looks mostly fine. She has a very curvy mom-bod, which is fine with me. She is the definition of PAWG. Whooty even.

Imagine Virgo Peridots body type only a decade and a half older.

I call the attached phone number to voice verify with them. Turns out the woman’s fiance is her new “career” handler, manager, cameraman, and promoter. I chat with them about what they are looking for. They are looking to have a group of guys over at a hotel near their home in the New Port Richey/Hudson area which is northwest of Tampa. They will be videotaping the event. There will be two other women there also to provide fluffy support I’m informed. They said party favors are appreciated but not required. They prefer snow skis or possibly a girl named Tina Krystal. I don’t ski or know any girls named Tina Krystal. Not my thing however “you do you” I reply back. However, I do offer to bring a couple handles of liquor though and they are cool with. In true Craigslist fashion, they tell me they’ll email me with the location and day at a later date.

I figured I would not hear from them again. Color me surprised when I get an email a couple hours later from them with the details. The date and time was set for the following Saturday night. Fantastic.

I refrain from jerking off for the next five days. Yes, it did indeed suck. I am naturally a heavy cummer and I have almost no refractory period. This means I can cum multiple times and keep on fucking. I am prepared to give this session my best.

Saturday finally rolls around and I spend the day resting and drinking lots of water in preparation for the evenings possible carnal events. I make my way from the Tampa area up to NPR/Hudson.

I arrive a little early to do a drive-by of the hotel to check the scene. Not a lot of cars and the hotel is actually a very rundown motel/notel. Ehh, I’m a little concerned but not too much. These situations can sometimes be a set up for a robbery or something even worse. Fuck it. I drove over an hour to get there I will at least check the vibe.

I cruise past the location and head to the nearest liquor store to get the two handles of liquor.

After, I pull into the motel I squirt two shots of Yohimbe extract under my tongue, lock my car up, and head to the room. The door is answered by the guy I talked to on the phone earlier in the week. Pleasant guy who introduces me to the rest of the assembled crew. All in all there are a total of three women and three men not including the main woman’s fiance who will just film the evenings events. I’m good with all of this.

The amateur porn star wannabe, and I say this kindly, comes out of the bathroom adjusting her spaghetti strap t-shirt and pulling the denim short-shorts out of her camel toe. She laughed and excused herself jokingly. She looks very good. Much better than her pictures for sure. She definitely does some tanning in the hot Florida sun. Beautiful skin tone the color of dark golden honey. Her waistline is much more slender. I would say that she has an extremely curvey exaggerated hourglass figure. I love women of all shapes, sizes, and colors however, her shape and size get me rock-fucking-hard instantly. It is what I prefer.

The mixer begins and everyone is talking and being cordial. The two other guys are respectful and laid-back. One dude looks like the professor from Gilligan’s island and the looks like Dollar General version of Eminem.

The two other women, a brunette and redhead are late twenties spinners. Little titties, cute little butts. Both little and petite with their hair already tied up in the Ho’ Bun style. They mention that they both have stripped at the low rent clubs up and down US19. The two spinners and the two other guys go into the bathroom to assumably do some party favors. Ten minutes later the young women are mostly nude on one of the two beds making out and rubbing on each other. Dicks start coming out of their pants and a circle jerk ensues around the bed. I pull my cock out and slip on my favorite metal cock ring.

The older woman asks me to come over and unbutton her denim coochie cutter short-shorts and slide them off of her. I oblige her. She is standing drinking a liquor drink and watching the two girls making out and the other two guys beating off watching them.

I walk up behind the hot older woman and put my hands on the soft curves on her waist. Like I mentioned before, her body type puts the fucking lead in my pencil so to speak. I run my hands around her waist to the front of her jean shorts and start unsnapping the buttons slowly. I run my fingers between her skin and the waistband of her jean shorts to loosen them up as they are beyond tight. I start to pull them off and her big fat ass is resisting the denim waistband. The shorts are almost too small. With a little forceful tug I get the down past her beautiful ass cheeks. The come to rest where her legs meet her ass. I grab a handful of her soft luscious booty several times before removing her short-shorts completely.

I’m throbbing hard and my cock is ready to bust out of my loose basketball shorts now. I move in and rub up against her thonged ass and slowly dry-grind on her plentiful ass crack. I excuse myself momentarily and back up off her while I pull off my shorts.

My dick springs the fuck out of my shorts and thumps the side of her big butt with a smacking thud. Her ass cheek and my meatstick recoil in motion.

I go back to her waist and get bold and kiss her neck behind her ear. She grabs her dirty blonde hair and moves it so I can continue kissing her there. This was the reaction I was hoping for and received! I quickly run my tongue down her neck and then back up towards her ear. She lets out several quiet moans and then reaches back to pull me closer to her from behind while we’re still standing. My precum is flowing heavily now as I slide my cock down into her ass crack. I’m hotdogging her ass cheeks from behind and my cock head is bumping and pushing her pussy mound. She reaches down and rubs my wet cock smearing my clear semen on her bald twat. She then immediately turns facing me and sits down and back in the rooms chair.

As she is leaning back in the chair, she is also pulling her legs up and bending her knees sharply. With her legs spread wide open and pulled up and back her pussy is now fully exposed. She is pulling her glistening cunt wide open and shallowly finger fucking herself and guzzling a liquor drink steadily. It’s fucking hot and I’m letting her know that I’m loving what I’m seeing by stroking my hard veiny cock, it’s head dark purple and steadily leaking clear precum.

She is giving direction to the two younger women on the bed. She then pulls her spaghetti strap top down to expose her massively gigantic tits. I am next to her and leaning against the dresser/tv stand lightly stroking my hard cock trying to maintain a balance by grazing it. Just barely touching my freshly shaved dick and nuts. I am pulsing hard and the veins in my cock are fully surfacing which she compliments me on.

It is hot as hell which is the norm in summertime Florida. The raggedy window AC unit is just not cutting it. I have low hanging rather large balls and they are trying desperately to stay cool now. The older woman reaches over and strokes my thick hard rod several times and then grips my nuts and pulls me closer to her and starts to lick and suck on both of them. This one, then that one and then both pop into her mouth.

I look over at the bed and one of the young women is blowing one of the other guys cocks. The professor guy blows his wad quickly with a pinched face and clearly has a moment of post nut clarity embarrassment. He quickly pulls his shorts back on and mumbles an excuse to leave quickly. Slightly awkward but this will only play into my favor, so adios dude. The other remaining guy quickly puts his cock into the spinners super wet mouth and starts to face fuck her vigorously but with care. She is doing the gagging gurgling thing and enjoying it.

The older wannabe porn star is playing with my balls while I stroke off watching everything that’s going on. She is enjoying the smoothness of them and jokingly says “at least someone prepared for this! I nod in agreement and rub my bulbous cocks purple head while she is rubbing and licking my smooth nuts. I softly jelq my cock from base to tip forcing a long sticky stream of precum to exit my penis heads mouth.

The older woman immediately holds her hand under the stream and catches it, brings it up to her mouth and licks it off her hand without breaking eye contact with me. In all seriousness, this woman is well versed.

I tell her how hot that was to watch and she says “oh yeah?” and proceeds to engulf my cock in her mouth. My dick involuntarily flexes and bounces hard. My metal ringed cock grows in girth and she vocally “hrrrmmps” with my dick deep in her throat. After a short sensual throating she excuses herself to the bathroom to powder her nose.

I sit back and watch the live show on the bed. The two younger woman are both giving head to the Dollar General Eminem.

The older woman comes out sniffling and plops on the bed pulling her knees behind her arms. Her hips are very wide and her quim has a fresh slathering of lube on it. Her fiance hands her a large dildo. She starts slapping her pussy with the dick shaped unit barking out “get that pussy! get it! get in that fucking pussy!”

She slaps it harder and harder and finally plunges it into her hot box. She has a full audience now. We are all watching this hot scene. Everyone is stroking off.

The plunges get more and more intense. The dildo get buried to the hilt over and over as the room fills with that unmistakable smell of beautiful cunt-hole musk. Feels like the room is humid from her snatch. One of the spinners goes over to her and pulls the dildo out of her pussy and devours it, licking off all of the pussy gruel and then reinserts it back in the older woman pussy.

The older woman asks me and the other guy to both slap our cocks on her pussy alternatingly.

He slaps, I slap, he slaps, I slap….

She adds her hands to the mix and starts to rub our two cocks together on a circular motion and then on her pussy. She is sopping wet. She is extremely turned on.

After a few minutes of this her pussy is now starting to sop gruel heavily. Her hips are bucking like she’s being fucked by a phantom cock. She asks us to tease her harder. We then take turns quickly sinking our cock heads into her hot hole in rapid succession. Just a few plunges at most then the next guy dives on. Back and forth repeatedly. Fast tagging-teaming her pussy ensues. The other guy is doing practically the same as I by flexing short loads of precum into her pussy each time we’re in her pink entrance. Her pussy feels amazing.

I might like to add this; wearing a good fitting metal cock ring exponentially enhances what you are able to feel from you dick if that makes sense. This woman’s pussy feels VERY textured. I can feel it intensely and immensely. Very rigid feeling.

She is super into it. And asks that we start to go deeper and no more than a few long strokes each unless she says more. We oblige her request. Again, her pussy feels amazingly textured. Like hundreds of little tongues flicking the entire cock on its way to the deepest depths. We each bump her cervix which to my surprise, she greatly enjoys.

The spinners were there to provide hand and blowjob fluffing. However, one of them is clearly turned on and is now in the chair fucking herself with the older womans dildo she had been previously using on herself. It’s a hot thing to watch an audience member getting off.

We hold back momentarily and just watch the older woman please herself.
She is apparently double jointed or something as she is self folding up. Her knees firmly behind her shoulders and her face a foot and a half from her pussy. It is a beautiful sight to behold especially for an overly thicc woman in her mid 50s.

Props to her for real.

She is insisting that someone get on top and stick a hard cock in her and fuck the daylights out of her. The other guy goes over a sticks his dick in her and starts furiously jackhammering her twat until he pulls out and cums a short hard stream onto her stomach and one of her large tits. He dives right back in and slows the pace down to fuck her steadily for several more minutes. He is profusely sweating and hops off of her quickly and says “next! I need a cigarette.” We all start laughing.

I go over and caress her wide hips and start to mount her but I hold her head so she can suck on my cock for a moment. I also hold her cum glazed titty up to her mouth so she can taste his cum. She licks it all off like a greedy slut. My cock is just throbbing with my racing pulse as I slap her pussy with my meat. I plunge into her hot hole and start pumping her in steady rhythm. The feeling is incredible and it is increased by the fact that her fiance is filming all of this. I pull out and stick my wet penis back into her mouth. The other guy remounts her and starts slow deep grinding in her and against her clit. One of the spinners leans over and begins sucking on her nipples. She is thoroughly enjoying this attention that she is receiving from multiple people. After several minutes I remount her and begin to re-fuck her well used pussy. The sloshing sound of wetness is amazing.

I pull out and shoot a single large white rope of hot cum on her stomach. I immediately re-enter her pussy and keep on fucking her. I hear a “hell yeah” from one of the younger women. The older woman says to everyone in the room, “the cum stays, all the cum, don’t wipe me off! It’s all mine!”

She flips over and I start fucking her doggy. This woman is rather incredible. Her flexibility is amazing. She arches her back so much that her pussy is gaping wide open and easy to access. It is pulsing hard also. Opening and closing. Opening and closing with the combined cum slightly dripping out. I stick two fingers in her and her pussy is absolutely cavernous. I could probably fit all of them in there. It wants to be satiated to the extreme.

I’m wanting to watch and refresh. I get off and the woman turns on her side and one of the spinners starts tongue fucking the older woman. The young woman’s face is totally glazed after being buried in the gash. Just sopping wet. The other guy lays behind her and puts his cock in her again. After several minutes he gets back up I lay on the bed and she mounts me cowgirl and we start grinding deep and slow. She says she likes the feeling of the cock ring up against the top of her clit she says. She starts grinding very hard in a motion that is causing her ass to shake in a way that is similar to twerking. I can feel the quaking with my hands on her hips but I wish I could see it from behind. It is unbridled and the natural rhythm of her desire to cum that is driving this. Her motion and repetition is excellent. Her pacing just right. She shakes violently and then quivers hard and long when she finally cums. Her pussy is gripping my cock and feels like it is sucking it back and forth hard up against her cervix with the head bent up towards her G-spot.

She is exhausted and now laying on top of me with my hard cock still in her. I keep the pulse going back and forth very slowly. She is winded and spent but still wanting more. I hold her ass cheeks open so her fiance can video tape the sopping wet mess that is her mess of a pussy with my cock still working slowly at drilling at her swollen red hole.

The participating spinner reaches over and starts to play with her asshole, eventually pushing her ring finger into her butt slightly. I can feel the pressure of her finger up against the shaft of my cock in the woman. It’s fucking hot. Essentially a DP involving a cock and finger.

The feeling is so intense that I pull the woman down hard on me to shoot several hot thick loads into her pussy. She meets me with her lovehole squeezed tight like a ring and milking my cock into her deepest depths. Her hairless pussy is squeezing and pulling as much batter as my pulsating balls would give her.

We are all soaking wet from sweat and cum. She rolls off of me and is laying spread eagle on the bed fanning her pussy with her hands. Her hole is leaking lots of combined cum. The other guy mounts her in mish and rubs his cock all over her snatch getting it lubed back up using the already deposited cum. He pushes back into her hot pussy. He jackhammers her again for a literal hot minute and cums in and on her pussy.

By now everyone is needing to cool down but before that…..you guessed, I mount her one last time and long-stroke her quickly to blow one last quick load in her. No regrets!
We gangbanged, more like group-sexed her as best we could that night.

As a footnote;
I emailed the older woman and her fiance a few weeks after that date inquiring about the video footage that he took. Turns out the data on the SD card he used was corrupt. The only footage that they were able to retrieve was of the professor guy who left embarrassed pulling up his shorts. That’s fucking it.

They asked in our last correspondence if I was up to do it again if they could re-arrange another date.

I replied, “of course anytime anywhere!”

Source: reddit.com/r/gonewildstories/comments/12qofsg/group_craigslist_days_revisited