The Delivery

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A pizza delivery turns into an evening of sexual exploration.
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DaniW
DaniW
761 Followers

Being fresh out of high school with no work experience made it hard to find a good paying job, so I had to take what I could get. Having a good car and being at least 18 years old were the only requirements to work at Anthony's Pizza and with good tips, you could easily make over minimum wage. Given the other options available, this seemed like a pretty good one. Not to mention you could take home any "burner" pizzas at the end of the night.

During my first week of work, I was waiting for orders to come in with a couple of the other drivers. They always got first dibs since they had been with the company longer. When the areas known for good tips came up, they'd always jump for those, which was an expected part of being the new guy. However, one day while waiting for orders, I noticed that an address in a lucrative neighborhood popped up. The other drivers saw the address and responded oddly.

"Jesse, you can take this one. All yours," said Bobby, one of the more tenured drivers there.

"Are you sure?" I responded, a little confused at why he'd turn away a potential big tip.

"Oh yeah, this one is all you," he responded in a tone that was hard to pinpoint.

"Cool, thanks," I replied, not knowing what I was getting into.

I grabbed the pie, tossed it in the warming bag and made my way to Glistening Lake, an affluent subdivision just 10 minutes down the street. My GPS did all the work, taking me to an enormous two-story home in the back of the subdivision. It looked like a mansion, and had to be sitting on at least 2 acres of land. I grabbed the warming bag and made my way to the front door to ring the bell.

When the door opened, I was greeted by one of the most beautiful creatures I had ever seen. She was roughly the same height as me (5'10") and had long blonde curly hair. She was wearing a two piece black bikini, which showed off almost all of her incredible body. She had long, toned legs that went on for miles. Her hips jutted out and formed into her perfectly shaped and robust butt. She had a trim waist that stretched up to two large, round D-cup breasts that were barely held in by her skimpy black top.

She had beautiful, green eyes and a small, slightly turned up nose. Her lips were thick, slightly pouty and naturally pink and when she smiled, she had the most alluring dimples. Her skin was perfectly tanned with no noticeable tan lines.

In short: she was the perfect woman.

"Well, hello there handsome. I'm Brandi, what's your name?"

I was stunned standing in front of her, and I barely even registered that she had spoken to me. Her words shook me back to alertness, making me also realize that I had been staring directly at her considerable breasts the entire time. She was fully aware and seemed to welcome the attention.

"If you take a picture, it will last longer sweetie," Brandi replied, smiling and winking at me as she did.

"Oh god, I'm so sorry. My name is Jesse ma'am. I've got the pie you ordered. That will be $15.73," I sputtered out, trying to regain my composure unsuccessfully.

I couldn't believe the guys at work turned this house down. They clearly recognized the address and yet volunteered me to take this order. What idiots, I thought to myself.

"Come in for a minute while I get you the cash, will you dear?" said Brandi, who had turned to walk back into the house.

I walked in behind her, watching her perfectly shaped and stunningly smooth backside move hypnotically with every step. Her bikini bottom was sparse to begin with, and the walking motion exposed most of her amazing ass to me. I couldn't take my eyes off her, and my cock had grown in response.

We walked over to a table in the hallway that had her purse on top of it. She reached inside and pulled out a $50 dollar bill, handing it to me. I immediately went to my pocket to pull out change before she stopped me and said, "No need dear. I don't need any change."

Wow, not only was she drop-dead gorgeous, but she was giving me over 30 bucks for a tip! I had truly hit the jackpot.

"Are you sure? That's way too much, honestly," I responded, unable to believe her generosity.

"I tell you what Jesse, if you want to earn the rest of that tip, there is one quick thing I need a favor with," Brandi responded

"Sure. I'd be glad to help," I responded, not even knowing what the favor was.

"I need you to put tanning oil on my back for me. I was laying out when you showed up. Can you do that for me darling?" Brandi responded in a voice so sexy, it nearly brought me to my knees.

I audibly gulped at the thought of laying my hands on this beautiful woman.

"I'd be glad to," I said. My voice cracked like a boy in puberty, which was mortifying. It also drew a slight chuckle out of the goddess in front of me, who had now turned and was heading towards her back-yard. I put the pizza down on the table and followed her out back.

As we reached her back yard, I saw an enormous olympic sized pool surrounded by the most expansive deck I've ever seen. Brandi walked over to a pool recliner and reached around to undo her bikini top. She turned to face me, exposing her amazing breasts to me. She was clearly not shy.

Her breasts were the stuff of dreams. They were teardrop shaped and incredibly robust. They spanned the entire width of her chest, filling every inch. Her nipples were dark pink and were poking out, and her areolas were large and oval shaped and of the same color. As she moved, her breasts swayed fluidly from side to side, the sight of which nearly made me cum in my pants.

Brandi then turned toward the recliner and laid down chest first.

"The lotion is on the table," she said, ready for me to apply it to her back.

I walked over, put some lotion in my hands, and proceeded to massage it into her fully exposed back. Each rubbing motion drew an "Mmmmm" sound out of her, which only turned me on even more. After a minute or two, I had finished applying the lotion, and wiped my hands off on the towel on the table.

"Jesse, I know you have to get back to work, but if you want to help apply more lotion to me later, feel free to come back in a few hours. My front still needs to be rubbed down as well," she said to me, nearly knocking me over with her words.

"I'm off work in an hour. I'll be back right after I'm done and I get a chance to clean up," I responded quickly, my brain not doing most of the thinking now.

"Mmmmm. That sounds wonderful. See you soon, sweetie," Brandi replied, sensually.

I made my way back to Anthony's and was greeted by some of my co-workers.

"Well, how'd it go?" asked Bobby, as I walked thru the door.

"Fine. She gave me a $30 tip," I responded nonchalantly.

"That's it? Nothing else happened?" said Gary, another driver who was listening intently as well.

"Nope. She gave me the tip and I was on my way," I responded, not wanting to reveal too much lest I get myself fired.

"Yeah, I'm sure she gave you her tip alright," Bobby responded under his breath.

The full meaning of that statement wouldn't hit me until later.

Finishing the job

-----------------------

After closing out my day, I got in my car and raced back home. I jumped in the shower, got cleaned up and nearly bathed myself in my best (and only) cologne. I jumped back in my car and raced back to Brandi's house like a dog in heat.

When I knocked on the door, Brandi answered it wearing the same two piece bikini from earlier.

"Oh, look at you Jesse. Prompt and ready to go. I like that," she responded upon opening the door. "Come in, sweetie. We're going to have some fun."

I followed her in, again watching her stunning ass as it swayed from side to side. My cock rapidly grew stiff, as I anticipated what was to come.

"I'm going to need you to finish the job from earlier, " Brandi said, as we made our way to the back yard again. She stopped at the recliner, turned around to face me, and proceed to drop her top again.

"Can you do that for me love? Do you mind rubbing my front side for me now?" Brandi asked, as she moved toward me, pulling my hands up to her perfect, large breasts. My hands instinctively began to massage the mounds, tweaking the nipples with my finger tips.

"Mmmmmm. That's perfect, Jesse. Just like that," Brandi said with a sexual purr.

Brandi stopped my massaging momentarily to pull my shirt off and to nearly rip my jeans clean off of me. She saw my rigid cock poking through my boxers and grabbed it softly in her hands. She slowly started stroking it while also drawing me close for an open-mouthed kiss.

After a moment, she reached both hands down and tore my boxers off of me. I was now completely naked in front of her, my 7 inches standing fully erect.

"I've got a surprise for you tiger. I hope you like it," Brandi said.

She began shimmying her bikini bottom to the ground. Between her legs was a patch of some sort that she pulled at. As she pulled the patch away, a large, pink hairless cock emerged!

Holy shit! Brandi was a transsexual! It all made sense now. The guys at work sending me here. The comments and questions after I showed back up. They knew about her and they sent me here as a joke.

What they didn't know was that I had a thing for transsexuals. I had found myself bored with normal porn, and through some curious exploration, had found myself absolutely enthralled with transsexuals. I had often thought about what it would like to be with one and now, here I was, with a stunning one standing naked in front of me.

Brandi's cock was beautiful and huge. It had to be at least 8 inches long - certainly bigger than mine, which was no slouch. As I stood there staring at her stunning body, the only word I could muster was "Wow."

A sly smile came across her face. Her cock began to stiffen in front of me, and I couldn't take my eyes off of it. Brandi drew us together, pulling our cocks next to each other.

"I take it you like what you see, love?" Brandi asked me.

"Oh god, yes. You're stunning," I replied.

Brandi began stroking both of our cocks with her hands. The feel of her large unit next to mine was incredibly arousing. Our faces met again as she stroked us off, our lips opening to let our tongues wrestle between our interlocked lips. My hands had moved back up to her enormous mounds and proceeded to massage both of them again while she continued to stroke both of our stiffened units in unison.

After a moment, Brandi let go of our cocks and grabbed my hand to walk me over to her pool recliner. She had me lay down, my rigid unit sticking proudly into the air. She repositioned herself with her face towards my cock, and hers pointing down at my face. She carefully straddled her hips over me, placing the head of my cock into her mouth. Even though I had never done this before, I knew exactly what to do, grabbing her cock with my hand and placing the head on my lips.

We began sucking on each other's cocks, her lips and tongue massaging the head of my rigid member perfectly. I did the same to her, occasionally taking my mouth off the tip to stroke her cock gently.

"Ohhhhh god, Jesse. That's perfect. More of that please. Oh godddddd," Brandi moaned as I continued to suck on her beautiful, perfect cock.

She continued to do the same to me, drawing me closer and closer to ecstasy. We laid there, sucking and licking and stroking one another. I could feel her large breasts press against me as she rested her body on me. More and more we continued. With each moment, our sucking and stroking grew more and more intense.

Brandi was bobbing her head up and down on my shaft with intensity, while I was stroking her large cock in my hand, occasionally placing the tip of it on my lips and running my tongue across it. Both of us were intently pleasuring the other and our bodies began to heave with uncontrollable, sexual energy.

I could feel my body begin to clench up as my cock started to fill with my seed. As if in unison, Brandi's body also froze. For a split second, our bodies froze at the same time - ready to explode together.

Suddenly, my cock began spurting my cum into Brandi's mouth. I had never cum that hard before, and I nearly blacked out at the intensity of the explosion. At the same time, I felt Brandi's rock hard cock also erupt into my mouth. Her salty, white cum hit the back of my throat, nearly choking me.

For nearly a minute, we laid together as our bodies shot our seed into one another. I had never done anything like this before, but it somehow felt completely comfortable. The taste of her was intense, but amazing.

After our collectively trembling subsided, Brandi stood up and repositioned herself to lay next to me on the large recliner. Our lips met once again, in a passionate and prolonged kiss.

"I'll be honest, tiger, I never know how someone is going to respond to seeing all of me. You, however, genuinely surprised me. I've never had someone be as receptive as you were," Brandi said exhaustedly, as she looked me in the eyes.

"You're amazing and that may have been the most intense sexual experience I've ever had," I replied back.

"Well, we're not done yet. There's so much more to come," Brandi said confidently, placing another long, satisfying kiss on my lips.

The kiss proceeded, our tongues familiarizing themselves with one another again. The feel of her large breasts pressing against me was incredible, and my previously exhausted cock suddenly found a second wind. Brandi broke our kiss and straddled me. She seductively cupped her left breast in her hand and moved it to meet my lips. I latched onto the large mound, sucking on it intensely, whipping my tongue back and forth across her nipple.

"Ohhhh, Jesse. Mmmmmmm," she cried out in pleasure.

I forcefully grabbed her and pulled her other breast to my lips, again sucking on it passionately while my hand massaged the other breast. My free hand reached down to find her cock, which had also begun to find its second wind. I began to stroke her as I held one breast in my hand and the other in my lips.

"Oh god. Mmmmmmmm," Brandi moaned out in guttural, sexual tone.

Suddenly, Brandi pulled away, whispering, "You're going to make me explode again, you minx." She reached over to the table next to us and grabbed a bottle. She squirted something into her hand and began to rub it on my cock. She also reached behind herself, apparently lubing up her ass as well.

"It's not time for me to explode yet, lover, " she said, as she began repositioning her body.

Slowly, Brandi began to lower herself onto my rock hard cock. As she spread her legs to do so, her massive cock pointed forward and upward, turning me on even more. I grabbed hold of it with my hand and gently stroked it.

I could feel her tight ass begin to envelop and surround my cock. It was a tight, incredible sensation. She moaned loudly as our bodies came together until I was fully inside of her.

For a moment, we sat there. My rock hard cock fully emerged into her and her rock hard cock pressing against me. She leaned forward, pulling me in for another passionate kiss. As we kissed, her hips began to move up and down ever so slightly. My cock began pushing in and out of her, the sensation clearly overwhelming her. More and more she moved up and down and more and more the motion became more pronounced.

The sexual sensation was riveting. As she bounced up and down on my cock, her large, perfect breasts bounced fluidly in unison. At the same time, her rock hard she-cock began slapping up and down on my body. With each second that passed, her bouncing got more and more intense and her sexual moans became more pronounced and loud.

"Ohhhhhh Jesse. Oh god, Mmmmmmmmmmmm. This feels so good," she cried out.

Her hips gyrated ever so slightly as she pounded up and down on my cock, which only made her look even more sexual with each movement. The sight of her rigid, large cock bouncing up and down was something I couldn't take my eyes off of, save for the sight of her massive breasts doing the same right above it.

"Oh god Jesse, I think I'm going to cum. Oh god!" Brandi yelled out as her body tensed up and her back arched backwards. Her ass tightened around my own pulsating cock, and my body clenched up as I began erupting hot, white cum inside of her.

Her cock - resting ever so slightly on my waist - began twitching and started to shoot out massive gobs of milky white cum. It spasmed and twitched up and down as it shot stream after stream of her womanhood for what seemed like hours.

"Uhhhhhhh. Oh god. Mmmmmmm," was all Brandi could mutter, as her cock continued to explode.

After a few moments, our collective orgasms subsided yet again. We had both just cum for the second time in less than 30 minutes, and we were nearly wiped out. Again, Brandi collapsed on top of me, meeting me for a soft and gentle kiss. As she laid on top of me, our cocks met one another between our bodies, resting side by side.

"I've never cum like that before. There's something about you, Jesse. You bring out the animal in me," Brandi said quietly.

"I've never been with a woman like you. You're a dream come true," I responded.

After sitting together quietly for a while, we stood up and grabbed our clothes to head inside. After a quick shower together, we both collapsed naked together on the massive bed in her bedroom upstairs.

New Experiences

-----------------------

The next morning, I awoke with Brandi nestled next to me. We were both still naked, and as the light of the morning sun crept in, it highlighted her perfect body, making it look angelic. She opened her eyes slowly, catching my eyes scanning her beautiful body. My eyes traveled all over her, admiring her the large breasts currently pressed into me, all the way down to her still sizable cock below.

"Your eyes betray you, as does your cock," Brandi said playfully to me as she became fully awake, noting my stiffening cock before her.

"How open are you to different experiences, Jesse?" Brandi asked me, as she gently grabbed my growing cock in her hand.

Sensing what she was asking, I responded, "Very open. I want to know what it is to be with you fully. Whatever you want, I'm completely up for."

"Ohhhh, I like that answer. I like it a lot," Brandi said, leaning towards me and planting a kiss on my lips. "I'm going to make you mine," she added seductively.

With that, Brandi moved to her knees on the bed, her hand still stroking my ever hardening cock. Each movement of her body screamed sexuality, with the way her breasts swayed and her own rigid cock bounced. Watching her body move was a turn-on by itself.

She popped up from the bed and to the nightstand, where she grabbed another bottle of lube. She jumped back on the bed, positioning herself between my legs. I was nervous at what we were about to do, but I couldn't wait either.

"Have you ever had anyone inside you before, tiger?" Brandi asked.

"No. Never, " I responded.

"I'll be gentle, I promise," she said reassuringly.

Despite my anticipation, I was a little nervous at what to expect. Brandi had a rather large cock, and given that I was a "virgin" so to say, this could end up going poorly. Yet, I was more than willing to give it a shot.

Brandi had put a little bit of lube on her fingers and began slowly inserting one into my hole. It was a strange sensation and my body naturally clenched up. She encouraged me to relax, which I did as much as possible.

Slowly, but surely, she continued to work on me, getting two - then three - fingers inside of me at once. The pain was definitely there, but she surprised me when she hit my prostate. An intense sexual sensation rushed up my spine, and my cock stiffened tightly at the pleasure.

"Oh, there it is. You're going to love this once we get going," Brandi said, a devilish look in her eyes.

DaniW
DaniW
761 Followers
12