The Daily Double: A Two-for-one Story

I think this one needs a bit of a preface… it’s long but it’s a ‘two-for-one’ story.

The preface: At the time of this experience, I had a great network of horny, highly sexual, uninhibited people that loved to play any time, all the time and I had an insatiable sexual appetite so I found myself increasingly seeking and connecting with new partners and experiences daily…occasionally multiple experiences a day.

Back at a time when Craigslist Personals were still a thing, I browsed them on occasion (and by ‘on occasion’ I mean daily) as a supplement to my favorite Adult Personals and every now and again CL yielded some great encounters – I’ll get around to writing about all of them in time. On one such occasion I was heading home late one weeknight after a post-work Happy Hour that ran late into the evening. Horny as always, I decided to cap off the evening by popping in for a quick blow job from a sexy friend, in Bloor West with whom I often visited for her exceptional deepthroat skills. Plus, I knew she was almost always up to meet and play. I hopped a cab and shot her an amusing text that I was a little drunk heading home but needed to ‘drop something off’ for her to which she responded quickly with an ‘LOL’, explaining that she was in her PJ’s going to bed and asked me how ‘urgent’ it was that I ‘drop it off’ right now. I playfully responded that it was very urgent, and I wasn’t sure how much longer I could hold onto it for her. She responded with typical good humour that I had then better get over and drop it off quickly so I diverted my cab ride and headed there.

Minutes later, she was greeting me at her door with Pyjama bottoms only, topless from waist up – worth noting that
she had fantastic large boobs that she was very fond of showing off and it was always a dilemma whether I finished between her tits or in her mouth – she loved both. She had a glass of wine already poured for me by the couch and she poked fun at my drunkenness as I pulled my clothes off and plopped down naked with stiff cock already at full attention….she settled in next to me with her own glass of wine, reached over and began to caress and play with my cock while she inquired about my evening. We chatted and laughed as we sipped our wine and she casually played with my swollen cock, alternating between lightly tickling my balls and making long slow strokes up my shaft. She was fully engaged in our conversation and not so much as acknowledging my swollen dick in her hand but after about 10 minutes of chatting, she could see that my focus in our conversation was waning and my eyes were now drifting down and lingering on her hand as it glided up and down my thick shaft. She said, ‘so about that urgent thing you had to drop off’. We both laughed as she slid down between my legs and engulfed my cock with her mouth.

I sunk back deep into the couch, laid my head back, closed my eyes and listened to the sloppy smack and soft purrs she made in rhythm with the deep wet mouth strokes. She had no gag reflex and was very proud of that, often showing off with long strokes that started at the tip of my cock and slid right down to the base with a final push to squeeze each stroke as deep as possible. Then dragging her tongue back up the base of my cock all the way back up to the tip again to repeat. I loved that I could literally feel the stages of each stroke on my cock…from her tight pursed lips popping down over my cock head and sliding down my shaft, her warm soft, sloppy mouth and tongue easing all the way down my shaft, and then her pause as my fat cock head reached her narrow throat, and finally the slow tight squeeze as she eased my cock into her throat until I feel her lips press into my pelvis. She forced my cock head into her throat with a back and forth wiggle of her head that squeezed and swirled the sensitive underside of my cock so amazingly that each down stroke made me twitch and think I might lose control, then with each upstroke, the pressure relented just enough to regain control and hang on for the next stroke.

And so this went on…hand rhythmically caressing my balls as she devoured my cock. I laid back soaking it in inching to the edge over and over and then easing back from the point of no return. With each retreat back from the edge I could feel the pressure building and I resisted each rush to release. I marvelled as I watched my big swollen cock disappear effortlessly, over and over and she loved to stare up into my eyes as she squeezed my cock into her throat. Eventually the pressure in my balls peaked and like a release valve, I could feel a thick volley of pre-cum flood into her mouth…I could see it in her eyes when the salty pre-cum hit her tongue and she sensed I was close.

She was almost predatory…Her cadence sped up and her mouth became an intense vice…she wrapped her hand tight around my shaft and pumped hard to coax me over the edge. I was ready to give in and I signalled I was soon cumming but then seeing her amazing tits hanging down on each side of my balls gave me the sudden urge to wrap them around my cock and use them to pump out my load. I leaned forward and whispered to her that I wanted to tittyfuck my hot mess all over her tits.

She stopped abruptly, and burst out laughing. In between giggles, she said ‘I was just getting ready to crawl into bed when you texted and came over you fucker, you better not spill a single drop of jizz anywhere that I have to clean up!’.
We both laughed hard for a few moments and I said, ok, ok…mouth it is!

With that, she dove back to work, and I drifted right back to the edge…this time over the edge. I reached down u*********sly with both hands and pumped her mouth…that primal involuntary thrusting that happens with each spasm of of cum…an intense uncontrollable reflex. I could feel my load flowing hard into her throat and mouth and eventually oozing down my shaft and pooling onto myself…when I opened my eyes, she was looking at me with a big cummy smile.

When I smiled back at her, She popped up quickly and plopped back down beside me, then grabbed her glass of wine and handed me mine while I still sat twitching and rubbing my sloppy dick. We sat quietly for a minute as I sipped in post orgasmic bliss. I very clearly recall glancing over and seeing that she was sipping from her wine glass with my cum still smeared around, including thick cum all over her wine glass. I’m certain she was making a show of it for my benefit.

My cock was still half hard and sensitive and I instinctively continued to stroked it while we chatted and finished our wine. As I played with my cock it stiffened again and we both realized together that there was a big hard cock between us again. She giggled and proclaimed, ‘Nice try!! I’ve seen this movie before…you made your drop off and now you gotta let a girl sleep.’. I teased for a bit, joking about a second ‘drop off’ but took a rain check instead and headed home for the night.

Fact of the matter was that this scene had played out already many times before as she was a reliably horny friend and we had been leaning on each other for frequent casual encounters just like this for a few months after connecting on CL Personals. It was comfortable and easy for both of us and we were both always game so we connected a lot. There was nothing unique about this time except that on this night, it laid the groundwork for the main story which is still to come.

The story: I got home and poured a night cap but couldn’t shake the twinge I had in my crotch. Sure, I just had an exceptional deepthroat BJ and emptied my balls but having left things with a renewed hardon, I couldn’t help feeling some unfinished business…I had a lingering feeling that I needed more so I plopped down at the computer queued up a little porn and picked up where I left off at her house stroking. I wasn’t gonna be able to sleep without another release.

I fired off a couple txt and emails to see who was still up for some play but after midnight on a weeknight I knew it wasn’t likely so I cruised through the usual Adult forums and CL personals to see if there was anything going on. Sure enough I found an Ad in CL for a couple looking for a late night rendez vous at a hotel on Dundas in Mississauga. A bit far out for me but I fired off a msg anyway – why not!?.

Minutes later I got a response asking me to call them which I did. I called and spoke to a dude who explained that they were in town from up north and wanted to video tape some porn with his girlfriend. He asked some standard fare questions and then promised not to show any faces in the film if I was cool with him filming my body and cock with his girlfriend along with a couple other dudes. It was 1am at this point and my good judgement was long since impaired by the alcohol so I said sure thing and immediately hopped into a cab to head out to Mississauga.

I arrived and knocked on the door and what a scene. The door swung open and the entire doorway was eclipsed by a giant man-mountain…he had to be 6’.5” and a very fat 350lbs…he was early twenties and was wearing nothing but a giant baggy white tshirt and droopy fruit-of-the-loom briefs. He was friendly and invited me in but I was thinking ‘wtf did I get myself in to?’. I stepped into a very tiny, tight room and scanned the room…there were 2 youngish dudes in the room, one standing to the side of the bed clothed and one laying on the bed, apparently naked under the covers from waste down.

Sitting in a desk chair at the desk, there she was….I was very pleasantly surprised…she was covered with tattooes, had her hair dyed purple, had a nose and tongue ring, and was wearing sexy black lingerie. She was curvy but tight and not at all what I imagined when I first saw man-mountain at the door.
Introductions all around…the clothed dude standing had just arrived also, the dude under the covers had shown up a little before and had already shot a load before I arrived and was hoping for a second round.

Man-mountain explained that he and his girlfriend had plans to start their own porn site online and make untold riches from the content that they were filming (I didn’t have the heart to burst his bubble about their chances of fulfilling their porn empire dreams). They were from some place way the fuck up in Northern Ontario (I can’t remember), and they had driven for 2 days, stopping and filming his girlfriend sucking and fucking dudes all the way down to Toronto where they were going to spend a few days filming as much porn as possible. They had a laptop on the desk and he queued up a bunch of the stuff they had been filming along the way so that we could check it out.

There was booze on the desk and they graciously mixed a stiff drink for everyone and said help yourself whenever you want. With drink in hand and already feeling comfortably numb, I parked myself on the edge of the bed. They showed a video they had filmed of her sucking a random cock right in a public mall…barely hidden from sight…it was risqué and hot…as I watched, I could feel my cock stiffen. Her eyes kept coming to it as we watched and so I reached down, popped my cock out of my pants and started stroking. I leaned back a bit to show off my cock that was now pointing straight to the ceiling and that got things moving. Man-mountain grabbed a hand held video camera and explained to everyone that he was going to start filming but that he would hand the cam off to everyone to participate in filming from all angles and views.

She moved into position in front of me on the edge of the bed and wrapped her fingers around my cock. The dude from under the covers was now moving to the other side of her on the edge of the bed beside me. He had a long slim cock that was also already hard too. We both laid back on the bed and she kneeled between us stroking both cocks up and down at the same time. The third dude stepped up beside her with a modest cock that she turned to and licked while she continued to stroke the 2 in her hands while man-mountain watched and filmed. It was a beautiful sight watching her badass tattooed arms pumping our cocks. I laid there sipping my drink while my cock got stroked, and marvelling that just a couple hours earlier, I was in a different part of the city with different company, watching my cock being deepthroated to completion. Life was good.

Man-mountain was now giving directions as he moved around with the Camera and instructed her to lay down on the bed with her head back over the edge so we could all take turns to fuck her throat. She obliged and we all took brief turns sliding our cocks deep into her throat...no gag reflex just like my friend from earlier in the night. I could see the outline of my fat cock head sliding into her throat with every push and we made sure to get an awesome close up of my big cock filling up her throat. It was only a short time later then when the dude with the long slim cock who had already cum earlier gasped and popped his cock out of her mouth and sent a long spray of cum down her neck, between her tits and halfway to her bellybutton. Several more big spurts then slide his cock into her mouth to clean it off. For a second load, the dude popped like a champ and we all had a good laugh with him about it as he took a seat to watch the rest.

I was sliding my fingers along her clit and into her very wet, warm pussy while I watched and now I wanted very much to feel her pussy on my cock. As she tugged and licked at my dick from underneath, I asked her if she wanted to feel it inside to which she said she wanted to get fucked hard from behind.
We made a quick adjustment and she crouched on the edge of the bed with her ass and pussy pointed up…it was a gorgeous pink with large engorged lips made for swallowing up cock. I positioned my cock head between her lips and slid in slowly until I was buried deep. I held onto both of her sexy hips and slid her back onto my cock, rocking her to work her onto my cock one inch at a time until I could feel her slippery, swollen clit pressed against my balls. I took long deep strokes and spread her awesome round ass cheeks apart as I buried my cock deep so that man-mountain could film perfect footage of my cock sliding in.

The other dude was now positioned beside her head on the bed and she periodically slurped and tugged on his cock as I kept up a good hard rhythm on her pussy from behind her.
After a few minutes, man-mountain handed the Cam over to me and asked me to film POV while I fucked her which I gladly obliged. With his hands now free, Man-mountain popped out his soft cock and positioned it directly in front of her face for her…it disappeared into her mouth and I filmed back and forth between my cock disappearing into her puffy pussy and her slurping mouth. It was only less than a minute when man-mountain slid his still soft cock out of her mouth and stepped back. She immediately barked at him in an amused, surprised voice ‘did you just cum?!’, and he sheepishly grinned ‘Yep’.

After monopolizing her pussy for a long time, I popped my cock out and swapped with the other dude who was enjoying her mouth but was patiently waiting a turn at her pussy. At this point, the first dude who already finished twice, decided a third round wasn’t in the cards and he let himself out.

I mixed another drink and got comfy on the bed with my cock positioned directly below her mouth and she gobbled and tugged it while buddy filled her pussy from behind. He pounded her good and long and it was clear that between the two of us, her pussy was going to get very well used.
Between the excellent load I popped earlier in the night and the free flowing drinks, I was in no hurry to finish up. The two of us took turns between her mouth, pussy, and hands rotating through a myriad of positions and she squirmed and moaned her encouragement through it all.

This scene played out for a long, long time…swapping from position to position around the room…impaling her juicy pussy on my cock, then giving up her pussy and using her mouth, taking the occasional break to mix a fresh drink, and she even continued jerking me off while I mixed drinks… all while Man mountain quietly filmed everything from every angle, occasionally giving direction on positions or handing the camera off for a POV shot.

Eventually, he directed us to stand side by side and let her work both cocks with her mouth which we did. She deftly managed both cocks simultaneously, alternating each one from her hand to her mouth and back again until the other dude grunted out that he was going to cum soon. I stepped back to free up her mouth and hands for him and she skillfully used them to coax him to finish…she squeezed and tugged his balls with one hand while hand pumping his shaft hard with the other hand as she sucked. Dude thrust in rhythm, panting and urging her on directing her faster, harder, don’t stop, and then finally, telling her that he was cumming. She sucked and hand pumped his cock, catching some cum in her mouth and the rest on her face.

It was a hot scene and I couldn’t wait to feel her soft tight pussy back on my cock again as I stood by stroking. I was reaching that pressure point…cock rock hard with urgency, balls swollen and in need of release. So, as soon the dude was empty and stepped back, I stepped forward and pushed her down on her belly on the bed, face and tits still smeared with hot cum. I straddled her sexy round ass with my balls dragging across her ass cheeks, squeezed her legs tight together, directed my cock downward and squeezed my fat cock head straight down into the apex of her thighs and ass until I could feel the slippery hot channel between her swollen pussy lips. I leaned into the tightness feeling my cock head then my shaft slip past her puffy pussy lips and into her sloppy hole. When I could feel my pelvis hard against her soft ass, I slowly started to pump. I was on all fours straddling her ass with my legs, squeezing her legs together tightly to squeeze my cock as I drove it down into her. My body was propped closely over hers so I could talk into her ear and I told her to squeeze my cock hard with her pussy as I fucked her deep…come on baby, squeeze that pussy tight, I told her…let me feel you squeeze this big cock hard…I told her to cum on my big dick and make me cum with her.

She whimpered and moaned as I fucked her and told her not to stop gripping my cock tight with her pussy. I squeezed her legs and pussy tight and drove my cock down hard into her, intent on driving her over the edge and straining hard to get there with her … I lost track of man mountain, the camera and all else in the room…I was focused only on driving my swollen cock into her tight hole and getting to that point of no return. Sweat was dripping, the smell of sex, the sounds…loud rhythmical slapping on her ass as I pumped as hard as I could, her moans, my primal grunts…I strained to get to the edge and be ready for any sign from her to let loose.

I reached around her body and as I slammed my cock down into her and squeezed her firm tits tightly in my hands feeling and squeezing her enormous rock hard nipples…this instantly made her squeal “fuck ya, fuck ya…don’t stop…I’m gonna cum”.

Note: Now is probably a good point to confess to the reader, and you may divine from my favorites, that I have a thing for boobs and especially tit fucking…it is absolutely irresistible to me to slide my cock between a sexy pair of tits until I explode. I’m a big cummer and it’s just a huge turn on to me to look down and watch myself explode and make a hot mess of a gorgeous pair of tits. So this should explain how things went next.

Feeling those sexy titties, and hearing her moan how she was going to cum, took me to the edge. I pumped hard for the home stretch and she exploded with a gush and moaned that she was cumming.
BUT now in a confluence of poor judgement from the alcohol plus having been denied from the tittyfucking finish in my previous session earlier that night, and now having these sexy tits squeezed in my hands right at this moment, I inexplicably made a ridiculous judgement call just as she is in the middle of a huge orgasm and just as I myself have gotten myself right to the edge of cumming…yes, at the worst moment…I was struck with the idea that I wanted to pull out, flip her over, and tittyfuck her to finish. And that’s what I did.

The moment the thought crossed my mind, I just reacted…bolted upright and my cock snapped out of her pussy, from between the apex of her thighs and ass cheeks, and snapped straight up. She squealed in what I can only imagine was total confusion and surprise. While still straddling her, I took her firmly by the hips and rolled her over while saying something to the effect of ‘come on babe, let me fuck those gorgeous titties…”
To her credit, she rolled with it like a champ…after the momentary surprise passed, even in mid orgasm while rubbing her thighs together and moaning, she also had the presence of mind to reach down and grab my cock and stroke while I slid up her torso and guided my cock into the channel between her tits. I firmly squeezed her tits around my cock which was slick and soaked with her pussy juices, and started to pump. It took a minute to get back to the edge but watching my swollen cock head pop up from between her cleavage and disappear again soon got me there…I groaned and announced to her and man mountain that I was going to cum

I’d later come to find out that it had been over 2 hours of pretty well not stop fucking sucking, and jerking since I had first arrived so with all of that build up, as soon as I went over the edge, I knew it was going to be a giant release. I bore down on her tits and pumped hard and the first volley of jizz erupted up from between her tits hitting her in the neck and chin and splashing outward. I pumped the next couple of big volleys of cum from between her tits leaving a thick sloppy mess from her neck down between her tits and then pulled my cock out from between her tits leaned over her and stroked my twitching cock hard for the rest. I shot several more volleys of cum now landing on her face and mouth while she stuck out her tongue as a target.

I stroked for a long time, I usually have a double orgasm and thought maybe I’d give her a double pop but with too many drinks, it wasn’t in the cards. So after I finished stroking, she took a hold of my cock, squeezed my balls and worked her hands from the base of my cock to the tip to milk out every last drop. Man mountain then spoke up and just said ‘holy fuck dude’.

At this point She was an amazing mess of cum all over the place and I felt very self satisfied at that moment that I had opted to finish the way I did however, a short while later as she was cleaning herself up, she half jokingly called me an asshole for pulling out while she was Cumming and I apologized profusely.
So anyway, that’s basically it…I got dressed and took a cab home…it was 5am when I got home and I had to get up for work. Totally worth it.

I really wanted to see the video that they filmed of the whole thing but I emailed them about it and they never responded. It makes me wonder if it’s kicking around out there on the internet somewhere. I hope so because it’s gotta be awesome! ?
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