How Did I Get This Lucky? Pt. 02

... continuation from Part 1

I did a little work around the house the rest of the day, but to be honest I spent most of my time replaying the night before. Was it a dream? The pain in my rear reminded me it was very much real. And every time I saw myself in the mirror, the streaks of jizz on my face were further confirmation.

I jerked off two or three times throughout the day. It was either that or have a perpetual boner as I couldn't get the image of Sam's terrific body and amazing cock out of my mind. It had truly been the best sex of my life, with the most beautiful woman ever.

Around dinner time I jumped in the shower, finally washing the dried cum off my face, cleaned up my butt, dressed in jeans and a sweater, and headed to the bakery for our date.

The front door was already locked so I knocked. Sam came to the door wearing a white sundress and some black high heels, looking stunning. She grabbed a sweater off the coat racked, locked the door and gave me a quick kiss. The cool night air made her nipples stiff and they lewdly pushed against the strain of her white dress. I wanted to dive down on them right there and then, but she wrapped her sweater around her shoulders, hiding the view.

"My eyes are up here, pervert," she joked.

"You look amazing," I said.

"Well, you certainly look more presentable without my cum on your face and beard," she chuckled.

"To be honest, I only washed it off about an hour ago," I admitted.

"You are one sick puppy, Darren," she replied. "Of course, that is why I like you. So, tell me, how many times did you jerk off today?"

"Ummm, welll, I kinda lost count," I said.

"Thinking about my cock each time?" she asked.

"Bingo. Although actually, I don't think I ever stopped day dreaming of your cock all day."

"Well, I'll have to give you some more thought provoking spank material tonight," she winked as she grabbed my hand and we started down the street.

I had made a reservation at a small Italian Cafe a couple of blocks down the street. It was romantic, and I already knew she liked pasta.

As we walked, Sam made a revelation. "I jerked off a couple of times today too, remembering last night. I had a hard time keeping my beast under wraps; sometimes it has a mind of its own. So I took a couple breaks, went up to my flat, and pulled out a load, remembering those amazing blowjobs you gave me."

Walking hand in hand through the neighborhood with Samantha, the owner of the popular local bakery, made me so proud. We looked like the perfect couple, even if nobody knew who wore the pants in our relationship.

During dinner, we talked and laughed like longtime friends. And equals. In public like this, Sam explained she didn't want to be Mistress, she just wanted to be Sam.

"But beware," she said, "At anytime I may turn back into Mistress and expect you to submit and obey."

"Works for me," I admitted.

I learned a lot about Sam that night. Samantha was born Samuel Johnson. She (I guess I should say he) went to the State University, studied computer science and law enforcement before going to work for the government. She ended up in covert operations, as a hacker and later an operative. Yea, a spy. Several years in, her identity was compromised on a mission and she was going to have to go into something like a witness protection program. The agency she was working for had been experimenting with some new drugs that allowed agents to go through painless gender transition, allowing them to continue their careers, unrecognizable to their original identity. She had always dreamed of being a beautiful woman and volunteered for the program. Her one demand, she did not want to give up her penis.

"Thank god for that," I had remarked, as she smiled wickedly.

The drugs were amazing, and within a year she had fully transitioned to her current look as Samantha Johnson. The funny side-effect of the drugs, not only did she not lose her male genitals, they were actually enhanced. She told me her cock had always been above average, but her current monster was a permanent result of the transition.

Jokingly she said to me, "Trust me Darren, my old dick was still bigger than yours. But my new one makes size queens like you drool."

The agency considered this a failure and ended the program. But she loved her new cock, other than the fact in seemed to ramp up her libido, making her constantly horny. She worked for the agency several more years until she retired on a healthy pension and opened her bakery. Since moving to the community, she had been in the closet about being a transgender female. Everybody thought of her as a woman, knowing nothing about what was between her legs. Like me, she pursued sex through online hookups, primarily with women. Again she mentioned her few forays into men had all turned out to be tranny "chasers," not interested in her as a woman at all, only wanting to have sex with her because of her cock.

She reiterated that although she loved being a woman, her sexual arousal was 99% focused on her penis. She was a top, she preferred being dominant in the sack, and while she was attracted to men, she mostly just wanted to use them. She would love to find a life partner, but that man better be as horny as she was, and not afraid to submit to her in just about every way.

I was touched that she opened up to me about her history. I reiterated that I thought of her as a beautiful woman first, with her big dong just an added bonus. But the whole conversation made me more horny to suck her off. Apparently the conversation had made her horny too.

She winked at me as she ordered the chocolate soufflé for dessert and said she understood when the waitress said that would take 25 minutes to prepare.

"No problem," she said, "Maybe we'll take a walk while we wait."

She grabbed my hand and pulled me up, leading the way. As we walked by the restrooms, a few individual rooms marked as unisex, she opened one of the doors and yanked me inside, locking the door. "Damn Darren, I can't look at that mouth of yours without wanting to stick my cock in it."

"That is what I like about you Sam," I chuckled.

"On your knees cocksucker. You've got roughly 20 minutes to work your magic on my horny dick," she demanded.

"Yes Mistress," I eagerly obeyed.

"Aren't you forgetting something?" she barked.

I looked at her perplexed.

"My cocksuckers are always naked," she reminded me.

Buttons pushed!!! I stripped down, fell to my knees, and hiked up her pretty dress. She was wearing a pair of light grey boy shorts under her dress, cleverly designed to tuck her big swinging dick back between her legs, hiding any view of her massive bulge.

I pulled down the lycra shorts and out sprang her big muscle, smacking me on the chin as it enjoyed its freedom.

I immediately went to work on her semi-erection, turning it into a throbbing boner in no time. Sam moaned quietly as I deepthroated her repeatedly.

"Oh yea bitch, that's what I was dreaming about all day. Fuck you are a great cocksucker," she purred.

As a cocksucker, I take great pride in my oral talents, and no matter what cock I am worshipping, I love hearing the cock's owner praise my efforts.

Sam slipped off one of her high heels, and started stroking my dick with her bare foot.

Pulling her cock from my mouth, I said "Mistress, if you keep that up, I'm gonna make a mess all over the floor."

"Why don't you jerk it all over my cock before you finish me?" Samantha proposed.

She didn't have to ask twice, and with a few strokes, I blew a chunky load all over her fat cock, before kneeling back down and engulfing her member. My cum worked great as a lubricant, and she grabbed the back of my head and gave my face a hard fucking, sliding deep down my throat with each thrust.

"OMG, I'm gonna shoot," she whispered, careful not to announce to the whole restaurant what was going on behind closed doors. "Sit back, open your mouth, and get ready for it slut."

The first few spurts landed on my tongue, but her eruption couldn't be controlled. Further spurts splattered on my face, drenching me in her seed. I licked her clean before she tucked her cock away in her boy shorts and straightened up her dress.

"Get dressed bitch, let's go eat some soufflé," she giggled.

I knew I had a thick load of cum all over my face and dripping from my beard and sweater I had pulled back on over my head, but she didn't give me a chance to clean up, as she grabbed my hand and pulled me back to our table, just as the dessert was being delivered.

"I hope you had a nice walk," the waitress commented as she put our dishes down, trying to stifle a giggle as she stared at my cum coated mug..

"Did you see the look she was giving me?" I asked, embarrassed out of my mind.

"Well, you do have a big load of cum all over your face," Sam laughed. "Don't worry, I'm sure she is more confused than disgusted. Besides, I can tell you love the humiliation. You have a boner right now, don't you whore?"

"Yea, I actually do," I replied.

We finished dinner, paid the bill, and took a walk through the nearby park as we headed home. Sam kept teasing me as we walked.

"How would you like to bent naked over that picnic table as I drilled your ass?"

"I can see you on your knees between my legs as I sit on that park bench."

"I'd love to watch you blowing some random stranger back in those trees."

At some point, I had to stop her.

"Sam, you are as sick and twisted as I am," I exclaimed. "And yes, I love all your ideas. But obviously neither of us can risk getting caught right here in our own neighborhood doing those things in public."

"Good point, D," she laughed. "Guess we'll have to go on vacation somewhere that we won't be recognized so I can defile you in public."

As we approached her flat, Sam squeezed my hand, turned toward me and gave me a long, deep French kiss, that made me weak in the knees. I truly was falling in love.

"I think we might have a future Darren," she announced.

"God I hope so," I answered.

"But right now, I'm gonna take you up to my bedroom, strip you naked, put you on your back with your legs up on my shoulders, and look you in the eyes as I fuck your ass," she said.

"Yep, falling heels over head for you," I replied.

We both laughed as she lead the way upstairs.

We left a trail of clothes strewed from her front door to her bedroom, as we went after each other like teenagers.

Sam tossed me on the bed, crawled on top of me, and sat on my face. "Start with my balls bitch-boy, and work your way towards my hole. Let's see if you eat ass as good as you suck cock," she challenged.

It didn't take long before I had my tongue buried up her rosebud and she was squirming and panting.

"Yep, your oral talents never cease to amaze," she laughed. "I'm rock fucking hard. You ready to get bred?"

"Yes, please Mistress," I eagerly answered.

This time her cock wasn't coated in my throat slime, so she reached into her bedside table, grabbed some lube, and slathered it on her boner and around my hole.

"Get on your back, with your ass on the edge of the bed, and put your legs up on my shoulders," she ordered. "I want to see your cum covered face as I shove my dick to the root up your horny butt."

Sam is about 5'6" tall, and her bed is pretty high, so the position wasn't perfect for her to stand on the floor and line up her weapon with my exposed ass. But clearly she had done this before and knew the solution, slipping back into her heels to bring her to the perfect height to access my bum.

She teased my hole with her glans, just barely inserting the tip before pulling back. "Does my bottom bitch want this big dick?" she teased, as she wrapped her fingers around my dick giving it a couple of light strokes.

"Stop teasing me Mistress. Shove that beautiful cock in and fuck me. PLEASE fuck me," I pleaded.

"Your wish is my command," she giggled as she skewered me on her rod, driving it deep.

"Oh my fucking god," I screamed, my eyes rolling back in my head as my dick squirted uncontrollably. I would never get used to her initial penetration, her penis was just too fat, but the pain was so fucking good.

"You look so cute impaled on my cock," she cooed. "You really love taking it in your butt, don't ya?"

"Best damn thing ever," I exclaimed, as I looked up at this beautiful woman that was fucking me with her wonder stick.

She pounded me good, alternating between deep slow strokes, and quick piston action, once in a while pulling it completely out and giving my swollen balls a few thumps with her boner before shoving it back in. At one point she bent over me, with her cock bottomed out, and gave me a long, sexy kiss. I reached down and massaged her perfect boobs, rolling those amazing nipples between my thumb and finger. She moaned approvingly.

This was no fast slam, bam, thank you ma'am fuck. By the time she neared blowing her wad, we were both sweating profusely. She grabbed my erection in her hand, and jacked me off as she built to her orgasm.

Within seconds I was spewing jizz like a broken water main, covering her chest in my spunk. This flipped her switch and she drove her dick to the hilt, shuddering with her own ejaculation as she bred me again, before collapsing on top of me.

"Wow," she cried, "with sex like that, I won't ever need to go to the gym again. I think fucking is the best ab workout known to humanity."

She rolled off of me and lay panting at my side.

"Did my little slut blow a good load?" she giggled.

"Yes Mistress, it was mind blowing."

"Well you certainly made a mess all over my titties," she chuckled. "A good fucktoy always cleans up his messes. Are you a good fucktoy?"

I didn't need any more coaxing and eagerly lapped my load off her chest, finally getting the opportunity to suckle on those amazing nipples I'd been admiring. By the time I had finished my snack, Sam was sporting another boner.

"Look what you did to me," Sam said, wagging her erection back and forth. "I'm gonna need you to take care of this before I can go to sleep."

Damn, this girl did have some stamina. She was wearing me out. But who was I to turn down another chance to suck her dick. It was like I was living in a porno movie, but with the hottest starlet that ever lit up the silver screen.

I took my time and really worshipped her cock this go around. Learning the little tricks that made her moan in pleasure. She had a very sensitive frenulum, and some targeted attention with my tongue made her leak like a faucet. And a good cocksucker never ignores the balls, especially when they contain that salty sweetness. I'd been having a hard time putting my finger on what her cum tasted like, but in the moment I was thinking of some citrus chocolate nuggets, filled with caramel, and sprinkled with rock salt. Thirty minutes later she fed me another load before we curled up and fell asleep. I was quickly becoming addicted to swallowing her seed, and a belly full of her spunk was better than any glass of warm milk before bedtime.

The next morning her alarm clock woke us at 4am again.

"I'm gonna take a shower before work honey," she breathed into my ear. "And I'm gonna need you to join me and take care of this pesky morning boner."

What a life I was leading, swallowing her load at night before bed, and another load first thing each morning. And getting my butt pumped full of sperm during the day. How indeed did I get this lucky?

As we kissed goodbye downstairs, Sam said, "I'll make you dinner tonight at my place. How about a steak? I mean, I do know how much you love meat."

Could things get any better?