How Did I Get This Lucky? Pt. 01

I'll start out with a confession. Ever since my divorce, I've become addicted to cock. I love sucking it, I love swallowing cum, and I crave getting fucked up the butt.

The problem is, I'm not gay. I wish I was gay. I wish I was attracted to men. But unfortunately I'm not. I love dick. I worship cock. But dammit, I have absolutely no romantic feelings toward males. I don't want a relationship with a dude, I just want his penis.

That leaves me in a weird sexual reality. I still love women; I love the way they look, the way they smell, their sense of humor. I love kissing women. I love cuddling and sleeping with women. I just don't find much sexual satisfaction from a vagina.

Now in my mid fifties, I've been divorced for nearly 10 years, my kids are all grown, and my ex is remarried. I am semi-retired, having sold the business I created some 30 years ago. I do some consulting work periodically, and trade actively on the financial markets, so while not rich, I make a decent living. I keep myself in good shape, regularly hitting the gym, jogging, and riding my bike. I keep my balding head shaved, have a pretty impressive but closely trimmed beard, and in all ways appear very masculine, even though I'm a total submissive bottom in the sack.

I'm in the closet about my man to man sexually preferences, which makes it somewhat difficult to hookup. I don't want to date men, I just want to suck them off or get bred. The idea of kissing a guy makes my stomach turn. I get an instant boner when I'm on my knees sucking a dick, but if the guy tries to return the favor, I go instantly limp. I can shoot my wad from getting pounded in the ass, but the thought of fucking a guy's hairy hole gives me the heebie-jeebies.

So, as you can see, I'm a total weirdo. I turn to on-line apps mostly to find sexual partners. That way I can spell out my likes and dislikes, chat and share photos, and identify alpha tops that just want to use a sub bottom like me. Mostly, the guys I hookup with are married or divorced, identify as straight, but aren't getting the sex at home that they desire. I'm just a surrogate set of holes for them to use in private to get their rocks off, which is absolutely fine with me.

All that said, I would really like to find a woman to spend the rest of my life with. Maybe a dominant woman, my age, that thought the idea of butt-fucking her husband with a strap-on dildo or maybe cuckolding him was her idea of fun. I don't have any idea how to go about finding somebody like that. Sure, porn on the internet is full of these fetish sites, but no way they are real, right? So until recently, I never saw that as a realistic goal.

But let me get back to my story. Around the corner from my house is a great little bakery called Sam's, owned and operated by a beautiful woman, Samantha, that I enjoy the occasional flirt, but she is way out of my league. She is probably about my age, but looks 10 years younger. It is clear she spends a lot of time at the gym, and doesn't just sit around all day eating her baked creations. And of course there is the whole "she has a vagina" thing. Yuck. She just doesn't appear as the strap-on wielding type, although I have fantasized about it. She is single, but I've never heard much of her backstory.

Anyway, before I invite a new guy to my place to have his way with me, I usually meet him at the bakery to make sure he isn't a psycho. We'll grab a table in the corner, have some coffee and a roll, and talk quietly about what we are planning to do before heading around the corner to my house to partake in some deviant man on man sex.

One day I was sitting at the bakery near closing time, waiting for a guy I met on an app to show up. I was on my third cup of coffee when I finally realized he must have flaked. Damn, I knew that picture of the fat hairy cock he sent me was too good to be true. Well fuck, now what was I going to do. I was horny as fuck and really needed some dick.

I pulled up my laptop and logged onto a few of the apps I use to see if anybody was in desperate need of my services. The bakery has great wi-fi and I was tucked away at a corner table as I perused some listings. Besides, it was nearly closing time and all of the customers were headed out.

To my surprise, Samantha pulled up a chair and sat down. "Did you get stood up, Darren?"

"Wha, wha, what do you mean Sam?" I tried to innocently reply, my face likely turning a bright shade of red. I quickly closed my laptop and looked into Sam's deep green eyes. She is a redhead with a lightly freckled face, the kind of woman I dream about, when I'm not dreaming about dick. She was wearing a pair of baggy jeans, tennis shoes, a cable knit turtleneck sweater, and a flour specked apron. And she looked beautiful.

"Who do you think you are kidding, Darren? I know your secret you naughty little cocksucker," she giggled.

"I don't know what you are talking about," I tried to act indignant. Yea, sure, I am a cocksucker, but how the hell did she know?

"Give me a break," she chuckled. "You've been using my bakery to meet your johns for over a year now. A steady flow of strangers meeting you here and then off for your perverted little sexual rendezvous. Don't try and deny it."

"Uhhh, what, oh fuck... how did you know. Am I that obvious? And by the way, I'm not a hooker and those guys aren't my johns." Sure, I was being a little defensive, but what do expect when somebody catches you red-handed being a cocksucking homo.

"OK not a hooker, but clearly a man whore. Well at first, no it wasn't obvious. You always seemed like a nice guy, maybe a little insecure, but masculine and you come across as straight. I assumed you were just meeting business clients or something. But I have plenty of security on my router and I can review all the dns and website domains that my customers access. Once I saw the sites you were viewing when you were in here, I did a little digging and accessed your accounts. I gotta say, you are one twisted cocksucker and bottom bitch."

"Jeez, are you some kind of software hacker or something?"

"Let's just say I haven't always owned this bakery. So, yea, something like that," she snickered.

"OK, I guess there is no keeping my secrets from you. So why haven't you kicked my pathetic ass out of here for good?"

"Well, I thought about it, but to be honest, all your promiscuity was fun to follow. You are one kinky son of a bitch and following your adventures always made me horny. When you first started coming in here, I kinda wondered if you were hitting on me, but once I learned how addicted to cock you are, I figured I was wrong."

"So you aren't completely disgusted by me, but why are you telling me all this now?" I asked.

"You looked so depressed when your latest fuckbuddy flaked on you, I just thought I could maybe help you out," she replied, as she went to the front door, locked it, and pulled the shades. I was the only customer left in the place.

"Sorry, Sam," I replied, "I find you incredibly beautiful, funny, and a real catch. But as you now know, I have some less than normal preferences in the genitalia department."

"Well thank you for the compliments, and I know what you like you nasty old pervert. It just so happens I have something that might change your mind."

Walking back towards me, she slipped off her apron and lo and behold there was a huge bulge in the crotch of her jeans. And given her jeans were on the baggy side, a bulge like that was mighty impressive.

"You might say I'm a woman with a little something extra," she laughed as she squeezed the crotch of her Levi's in a crude way.

"That doesn't look "little" to me," I choked out.

"Oh from your history, I know you are a huge size queen," she replied. "And trust me, you won't be disappointed in what I'm packing."

"Hmmm, that sounds like fun. How about..." I tried to spit out.

"Shut up," she barked. "I don't want to talk anymore right now. I want you to wrap those faggot lips around my meat and show me how good a cocksucker you are." And with that, she unbuttoned her jeans and whipped out the most beautiful cock I'd ever seen. Cut, with a huge mushroom head, bulging veins up and down the length which was way above average. Thick didn't begin to describe her member and her hairless nuts hung low in her wrinkled sack. Although her ballsack was cleanly shaven, the base of her pole was entangled in a mess of red pubic hair. Fuck did she have a sexy package.

"Oh my god," I exclaimed, "it is gorgeous." I fell to my knees in front of this goddess, my mouth literally watering.

"Strip cocksucker," she ordered. "Show me the respect my cock demands."

Damn if she wasn't a dominant woman too, but instead of using a strap-on, she'd be feeding me the real deal.

I stripped in record time, my very average penis throbbing with anticipation.

"Kiss it bitch," she ordered.

I gave her piss slit a wet kiss and was rewarded with a taste of her special sauce. It was without a doubt the most delicious pre-spunk I had ever enjoyed..

"Now give my balls some attention you horny pervert. Make love to those nuts," she barked.

Damn, I wondered if she was really this dominant or was just play acting based on what she thought I was after. Either way, I wasn't complaining as I licked and gently sucked on her girl-balls. They were slightly musky after being tucked in her jeans all day, but they smelled yummy, the most feminine scrotum ever. It reminded me of the smell of a woman's pussy, way more than the stink of a guy's crotch. Both of which I love.

"Very nice. Do you want to be my personal cocksucker Darren?" she cooed.

"More than anything Samantha," I replied.

I got a quick, stinging slap to my face. "When you are on your knees, you will call me Mistress," she angrily said.

"Yes Mistress, I'm sorry," I answered.

"Good boy. Don't let it happen again," she chuckled, as she swung her meaty member giving my bearded face a few gentle swats of her growing boner.

I started licking up and down the length of her cock, exploring every inch and feeling the veins throb as she grew to full erection. Swirling my tongue around the big bellend of her glorious tool, I opened wide and engulfed the first couple of inches.

"Oh my sweetie, you are a very good cocksucker. I guess you should be with all the practice you get," she laughed. "Do you like my penis?"

"I love it Mistress. It is the most beautiful cock I've ever had the privilege of worshipping," I genuinely meant it.

"I knew you would," she snickered. "I don't usually have sex with men, because it is not easy to find a "straight" man that loves women and cock equally. So I normally fuck women. But damn, women are horrible at sucking cock. You on the other hand... oh my."

She stopped mid sentence as I took her entire cock down my throat until her balls were resting on my chin. I had to fight my gag reflex as her fat hog filled my throat, but like she said, I did have many, many hours of practice. I kept it there for 15 or 20 seconds as I worked my throat muscles around her pole and licked her nuts before slowly backing my way off.

"Yep, you are one world class cocksucker," she sighed. "A male slut for sure, but a talented one."

"Thank you Mistress," I replied before diving back down on her dick.

She grabbed my head firmly in her two hands, and started face fucking me hard and deep. My own penis was rock hard and leaking as she fucked my throat, tickling my tonsils like they were a g-spot deep down in my mouth.

"Normally I have incredible staying power, but your throat is better than any pussy," she exhaled. "I haven't had a good blowjob in years. I'm gonna pop my load pretty quick."

Here I was, naked, on my knees, in my neighborhood bakery, getting my throat fucked by a beautiful woman with an amazing cock. And she was going to feed me her big load. How did I get this lucky?

She lifted up on her toes, arched her back, and I felt her cock stiffen noticeably; I knew what was coming. And boy did she cum. The first few jets went straight down my throat as she pulled back slowly, the next few filling my mouth. She shoved my head back as I let her big bulb pop out of my mouth, and finished shooting several thick streams of her scalding hot jizz on my face and beard, marking me as her territory. I swished the cum in my mouth around, admiring the taste of her viscous fluid before finally swallowing. It was easily the most scrumptious load I'd ever had the pleasure of enjoying.

Sam collapsed back on the chair, her legs trembling. "Holy fuck, that was incredible," she sighed.

I crawled between her legs and cleaned her monster with my mouth, making sure I got every last drop of her precious cum.

Looking down at me, she laughed, "You look so sexy with my sperm coating your face and beard. Did you have a good time, baby?"

"The best ever, Mistress," I replied, still slurping on her deflating member.

"Glad to hear. You up for more?" she giggled, as she tucked her big swinging cock back into her jeans.

"At your service Mistress," I said.

"Good. But first I need something to eat. Gotta replenish my protein for you honey," she laughed. "Let's go up to my flat and I'll mix up some dinner. Then I'm gonna fuck that hairy, faggot ass of yours and breed your hole."

She was my dream girl. The way she could vacillate between the sweet, sexy bakery owner I'd always known and the dominant, big-dicked, fuck-Mistress I'd fantasized about was priceless.

"Leave your clothes down here, you won't be needing them, and follow me upstairs to my apartment. Remember, when you are naked and servicing me, I am your Mistress. We can figure out exactly what our future relationship will be later, once my cock is fully satisfied and you are dressed again. Probably tomorrow morning."

Sounded good to me. The idea of spending the night with this beautiful woman, completely at her mercy, kept my dick throbbing. I knew if I even gave myself one slight little jerk, I was going to explode like Mt. Vesuvius.

Her flat above the bakery was very modern. A couple of bedrooms, a nice master suite, and a great room with an open kitchen that faced out to the street.

Pointing to the fireplace, she said, "Start a small fire while I get some pasta and sauce on the stove."

"Yes Mistress," I complied.

With a fire going and the pasta starting to boil, Sam said, "I'm gonna jump in the shower and get comfortable. Finish up in the kitchen, open a bottle of Pinot Noir, and fix us both a plate. I assume since you were planning to meet a man tonight, you are all clean and ready back there?"

"Yes Mistress," I answered.

I can't explain how submissive I felt walking around her nice home, naked, with a throbbing boner as I did her chores. All the while knowing I'd shortly be impaled on her huge cock. I have become quite adept at anal intercourse over the years, but her big, fat dick was still pretty intimidating. Not to mention, I did not want to disappoint Samantha.

Unbelievably, while I finished up my tasks, my cock stayed hard as stone. It was like I'd taken a little blue pill, but no, it was just the anticipation of being used by this beautiful goddess with her stunning cock.

As I set the plates down on her dining table, she sauntered back in, wrapped in a shabby flannel robe, barefoot, and with a mischievous grin on her angelic face. For a woman in her fifties, she had zero wrinkles, high cheekbones, and those light freckles that were really set off by her sparkling green eyes. She had her curly, long red hair tied back in a ponytail, and I'd have sworn she was in her thirties if I didn't know better.

"Grate some parmesan cheese on my pasta Darren," she ordered as she took a drink of the red wine.

"Yes Mistress," I obediently answered, careful not to poke her with my boner as I leaned over.

"I knew you were submissive from reading your online activity, but I assumed it was just the persona you took on in your faggot sex encounters. In your public life, you always appeared in control and somewhat normal. You really crave being submissive to a dominant person don't you?"

"I can't explain it Mistress. But sexually, I like giving up control and being used. I guess that makes me some kind of weirdo, but I'm in no hurry to see a psychiatrist and try to fix myself."

"Understood. And I don't think you are necessarily a weirdo, but you do have some alternative kinks and fetishes. Things I think I can work with and help you explore. Most guys that find out I'm a meat packing chick, either run for the hills, or immediately want to jump in the sack with me. I don't care for "shemale chasers" as it were. I much prefer to get to know a person before I stick my cock up their ass. I've gotten to know the public Darren over the last year, and I'm glad we now have the chance to explore each other sexually. I think we can have some real fun."

"I couldn't agree more, Mistress. I've had a crush on you for some time. You are beautiful, have a successful business, have a great sense of humor, and I've always thought we had a good connection. Finding out you also have a glorious cock, well, it is just the icing on the cake."

"Well said Darren. You may now pour me another glass of wine, cleanup the dishes, and get ready for dessert," she giggled as she sat back in her chair, letting her robe fall open. My jaw nearly hit the floor as I observed her naked body. I knew her cock was amazing, but damn, she had the most striking body, something out of a fitness magazine. Her breasts weren't huge, maybe b-cups but her nipples were very pronounced, nearly an inch long. I could imagine sucking on those beautiful cherries for hours. Her body was like an athlete, with a ripped set of abs, and long legs toned to perfection. The light freckles continued down her chest, set off by her milky white complexion, highlighted by her fading early Fall tan. Any twenty-something young lady would be envious of her physique. Oh, and of course there was her perfect cock hanging lewdly under her red bush.

Seeing me staring, she giggled, "You like what you see, fag? Isn't this way better than those fat, hairy old creepers you usually hookup with?"

Now I admit, as I've said before, I'm not physically attracted to men, other than their cocks. And in fact, it was true I normally had sex with guys like she described. But that didn't bother me at all, since I was after their alpha attitudes and horny dicks, not how attractive or ugly they were. But she was right, a beautiful woman AND a cock... WAY BETTER indeed.

"Yes Mistress, you are a goddess. Don't take this the wrong way, but I think I am literally head over heels in love with you," I chuckled.

"Hmmm, I like the picture of you heels over head, with my cock buried balls deep in your butthole," she laughed. "Now finish cleaning up and get back over here. I'm gonna need a little of your oral assistance to get my beast woken up and ready to breed you."

I finished off the dishes and was on my knees between her legs in record time.

"You need some more of this?" she teased, as she spanked my face gently with her heavy, soft cock. Even limp, she was nearly 8" of meat, significantly bigger than me. I love cocks that are still long and fat, even when they aren't at full erection. And damn did I love her cock.

"Yes please Mistress," I begged.

"You know you still have some of my dried cum in your beard?" she giggled. "I had to stifle a laugh as you ate pasta with a face painted by my dick. You like being my little cumdump don't you?"

"I'll never wash my face again," I kidded.

"Oh, if this works out, you'll be out in public with my jizz painted on your face quite often," she laughed.

Damn, she really knew how to push all my buttons. Humiliation goes hand in hand with submission in my library of sexual fetishes.

"Now get to work, cocksucker. Bring my beast back to life, and I'll give you the fucking of your life."

Five minutes later, with a sore jaw I had her back to 80%.

"Good work bitch. Let's retire to the bedroom and I'll let you finish getting me hard," she said.

As she got up from the chair, she let her robe fall completely off. Following her, I gawked at her firm, round, dare I say perfect ass. She usually wore baggy jeans, probably to help hide the bulge in her crotch, and I knew she had a good ass, but oh my god.

"Do you like my ass, queer?" she asked, giving it a little wiggle.

"Outstanding Mistress," I choked out.

"Good, maybe I'll let you eat it out later. And if you are a very good boy, I might someday let you fuck it."

As a rule, I have no interest in fucking a guy's ass, but the idea of banging this beauty made my dick leak a few drops.

"Jump up on the bed cocksucker, on your back, with your head hanging over the edge. With all your experience, I know you know what is coming," she purred.

Did I ever. I love getting my face fucked like this, giving up all control as a cock uses my mouth and throat like a pussy.

For another five minutes she deep-dicked my face, letting her balls slap off my forehead as she repeatedly drove her spear down my stretched throat. A couple of times, she reached down and gave my nipples a hard tweak, causing my dick to shoot a little.

"Does my little faggot like that?" she laughed. "Oh, I guess you can't answer with my prick shoved down your pie hole. But based on the copious amounts of sissy-sauce leaking out of your little clit, I can tell you like it. Not surprised, you do like a little pain with your pleasure, huh?"

Again, she seemed to know exactly how to push my buttons.

She finally pulled her now fully hard boner from my mouth. "OK, slut, time to see what that hairy little hole of yours feels like. Flip over, scoot onto the bed, and get on all fours. I do like fucking a hairy hole, reminds me of screwing a hairy pussy, only so much tighter."

I instantly assumed the position, arching my back and tilting my hips down. I knew I wasn't virgin-hole tight, but given her prodigious girth, I also knew it was going to be a tight fit.

Sam reached down between my legs and scooped up some of the jizz I had been leaking, rubbing it around my exposed hole. She gave my dick a couple of quick jerks, then squeezed me hard at the base, ruining any potential orgasm, but again making my dick squirt some cum. She lubed up her fingers with my sperm, and inserted one, then two, then three fingers into my puckered hole. I was moaning like a bitch in heat when she finally pulled out her fingers and lined her missile up with my horny hole.

"Between that sissy-sauce and the throat slime all over my cock, I think I can wedge this fucker up your pussy now," she chuckled. "What do you want now, whore?"

She was going to make me beg for it.

"Please Mistress, I need your cock up my ass. I need every inch of your powerful tool deep in my bowels. I want you to fuck me hard, deep, and long until you breed me and make me your bitch."

"Of course you do" she barked, and with one powerful push, she shoved half her cock up my ass. Yea, I thought I was ready, but I was stilling seeing stars. Sure it hurt, but it hurt so good. She kept about half her length buried, letting my rectum adjust as she reached around and tweaked my nipples hard again. With a satisfied groan, I pushed back against her, driving her rod deeper up my butt.

"Oh, my little butt pirate likes it doesn't he?" Sam exclaimed. "You are nice and tight, just like I like it. I can't wait to pound you like a cheap slut."

And before long, she was sawing slowly in and out of my hole, her balls bouncing off mine as she was bottoming out. I swear, I thought her cock was going to split me in two. But after a couple of minutes of this slow action, we began to grind in rhythm, Sam picked up the pace, and sure enough, she began pounding me hard and deep.

After about 10 minutes, she collapsed on my back. "Gotta pace myself bitch," she reflected.

I could feel her nipples, hard as diamonds raking across my back and she breathed deeply, catching her breath.

I began squeezing my ass muscles, massaging her cock impaled up my butt.

"Wow, that feels great Darren," she gasped, "You really are a talented little slut. But if you keep that up, I'm gonna flood your ass sooner than later."

My initial thought was I wanted this to go on forever, but then I figured we had all night. And hopefully many nights to come. The sooner she bred me, the sooner I'd get her unbelievable cock back in my mouth and again up my hole. This was going to be a night to remember.

"Fuck you little whore, you are going to work a load out me," she barked as she resumed her assault on my hole, grabbing my hips and starting to fuck me with abandon.

Within a minute, her constant stimulation of my prostate was just too much for me to handle, and with a loud grunt, my dick exploded, sending wave after wave of orgasmic pleasure coursing through my body. I would have collapsed on the bed, but Sam was holding me tightly by my hips as she continued pounding me.

"Did I make you cum like a sissy whore?" Sam exclaimed.

"Yes Mistress, you fucked the cum out of me," I moaned.

"Well my turn," she laughed.

I didn't think it possible, but she started fucking me harder, and before I knew it, she was pumping what felt like gallons of her sperm deep up my tortured hole. Fuck, I was going to have her spunk dripping out of me for days.

Slowly, she started pulling her fuckstick out of me, until I heard it pop out of my gaping hole. Yea, like everybody says, I felt so empty.

"Are you my personal little fucktoy now Darren?" Sam asked while gasping for breaths.

"Yes Mistress," I replied, as I turned around, took her spent cock in my mouth, and started cleaning her off from base to tip.

Her dick nicely cleaned, we collapsed back on the bed. I wrapped my arms around her and said, "That was the best fuck ever. Thank you Mistress."

"Yea, it was pretty fucking great Darren. You are one horny little slut, and I'm going to enjoy using you as my personal cumrag."

"Sounds perfect Mistress," I said.

"Let's get a little sleep," she replied. "For now, you can stop calling me Mistress."

"OK Samantha, Sam," I replied.

"But don't get the wrong idea. I own your mouth and your ass, and I'm still the one in charge. Got it?"

"Oh Sam, not only do I get it, I love it."

"I knew you would," she sleepily yawned, as we curled up and fell asleep.

Sam's alarm went off at 4am, as she needed to be down in the bakery to get the kitchen started. We were both exhausted, but to my surprise, she had a raging case of morning wood.

"Suck my cock for me Darren," Sam whispered, wiping the sleep from her eyes. "I'd much prefer feeding you my load over jerking off in the bathroom sink."

I happily obliged, swallowing another gargantuan load from her seemingly always horny cock.

As she brushed her teeth and threw on some clothes, she mentioned, "Don't forget your clothes are downstairs. You better go get dressed before the bakery staff get here. I don't want to have to explain to them why a naked man, with cum dripping out of his ass, and more jizz dried on his face is sneaking out of my apartment."

"Great point," I replied. "Will I see you later Sam?"

"Fucking straight you will. Be back at the bakery at closing time. You are taking me out for a nice dinner, before I bring you home and have my way with you." With that, she gave me a deep, passionate kiss and patted my bare bottom. Her full soft lips were like kissing clouds, and I actually wondered for a second what they would feel like wrapped around my dick.

"Yes Mistress," I winked as I headed for the door, my jaw still aching, my ass sore, but with a huge smile on my face. Fuck, that was the sexiest kiss I've ever received, and it was from a beautiful woman with a cock. How did I get this lucky?

... to be continued