A Bachelor's Dream

Being a bachelor at 27 definitely has its perks. I won the lottery last year, after taxes it was just shy of 5 million. I've been able to live quite comfortably, as you can imagine. I used 3 million to hire an investment group so I can live off the money I get back (not that I understand how it works). I put 1 million away for a rainy day, and I spent the rest on a decked out loft and a reliable car.

I'm not the most attractive guy in the world, but being 6"1' definitely helps. I have a total dad bod, tan skin that thankfully gets darker in the summer, and a nice head of curly dark hair (which I think is my best feature). In my hometown, I live like the king of bachelors, never worrying about anything and having all the freedom a man can hope for. Everything is exactly how I want it to be, but there's always a sense of loneliness that no amount of booze can cure.

That's why I'm jealous of the neighbors across the hall. Samantha and Kyle have been living across from me since I moved in, we might have even moved in around the same time as well. Even though theres no immediate signs that they don't have a great relationship (I.E. screaming matches or constant theatrical drama), I still get the feeling that Samantha could do so much better.

Samantha is the embodiment of sexy. She's 5"4', has straight blonde hair that goes just past her shoulders, and a cute face that reminds me of Kat Dennings. Along with freckles that would make any e-girl jealous, and her body is a perfect hourglass shape. I'm no good at eyeballing cup sizes, but if I were to guess, she would be a C or D cup for sure. If she would wear something tight, her ass would hypnotize any man. She has a wide smile and a laugh that lights up any room. Her voice is soft yet profound. She could voice act anime women if she wanted to.

Her boyfriend Kyle, on the other hand, is remarkably unexceptional. He's 5"8', abnormally average build, and his hair has a constant greasy sheen. I've only had a few opportunities to talk to Samantha, whether we're getting our mail at the same time or she gets back from work and I'm smoking a cigarette on the front steps. But every time we talk, she tells me more and more about their life. She's told me about constant issues Kyle just won't fix about himself, or what bills they've fallen behind on because she works full time as a bank teller and Kyle works part time at a gas station. I've given her a little money before, for groceries and a phone bill, and she's always been so grateful.

"Don't worry!" I tell her, "It doesn't hurt me at all, and I hate to hear about your stress."

She always says, "One day, I'm gonna make it up to you!" in that beautiful anime girl voice of hers, and you can imagine how many times I've jerked off imagining just how she'd repay me.

Today is when those fantasies seemed like they could come true. I was sitting on the steps, smoking a cig, when she came walking up to me.

"Hey!" she said while giving me that beautiful smile "Work was tough today, can I bum one?" as she put her hand out.

"Sure," I replied as I opened the pack for her "I don't think I knew you smoked. That bad huh?"

That made her chuckle.

"It seemed like everyone wanted to make sure I earned my money today," she said as she lit the cigarette and took a long drag. "I can feel the stress seeping out of my pores!"

When she said that I couldn't help but imagine what it would be like to give her a back rub, looking at that amazing ass as I kneaded her like some bread.

"Well at least its over now. Time for some much needed relaxation huh?" I joked.

She seemed less tense already.

"I got a nice bottle of wine and its all yours if you want it!"

She lit up as soon as I said that.

"I would love you so much!" she exclaimed "I don't think I've been able to drink in so long!", she laughed as she said that and looked at me with pure joy.

"Kyle is going to be out on a boys trip for a few days, I can finally get some stuff done around the place."

She put her cigarette out and I got a brilliant idea.

"Why don't I come over and help you pick up tomorrow?" I asked with a plan working itself out in my mind "I could pick us up some drinks and we can knock it out?"

The look she gave me a look that made time stop.

"You'd do that for me?" she asked "I don't want to put you out!"

I put my hand up in protest "It's not a problem. I got more time then I know what to do with. I promise!" and with that my plan was set in motion.

She told me she works a short shift in the morning and would be home around 1 or 2ish, and I told her I'd pick up some cleaning supplies and be over whenever she's ready.

Waking up that morning I had a full proof plan; buy cleaning supplies and groceries with the idea of making some dinner for her. If the day was going really well. Plus getting strong but tasty wine to loosen us up when we were finished. When I had everything, I needed I took a long, hot shower and played the whole night in my head, rubbing one out to the thought of her moaning in my ear as we fucked on her couch. 2 o'clock rolled around and I knocked on her door with all the bags in my hands and when she answered the door I had to use all my strength to not pass out right there. She was wearing a loose fitting crop top and sweat pants that seemed to cling to her beautiful figure.

"Wow you were serious huh?" she asked while looking at bags in my hands "Well don't judge me, this place gets out of hand sometimes" she said exhaustedly while she opened the door.

Her place was 3 levels above cluttered, nothing too crazy but definitely not a place she deserved to be in.

"Hey I've seen worse, and we got some liquid motivation." I said while gesturing to the wine "Let's get this knocked out so you can start relaxing for real!"

We spent about an hour going through and cleaning her place. It was hard not to stare as she worked. Her sweatpants made me realize just how much I wanted to experience what her ass felt like, the way it jiggled slightly but still seemed firm enough to spank and hold. Her tits seemed to want to jump out of that crop top every time she bent over. I had to hide my boner while we worked. I couldn't let her get uncomfortable now, not when the plan was going so smoothly! We drank as we cleaned and she became more and more giddy, laughing at my jokes and making some herself, and a few times I swear she looked at me with more than just a friendly eye. When we finished, I suggested I make some dinner and she seemed genuinely shocked.

"I can't ask you to do that!" she protested, "You've done so much already!"

"I insist!" I said as I opened up the fridge and took out some ingredients, "I got nothing going on, and a hardworking woman like you deserves it!"

I swear I saw her blush for a moment but she turned away quickly.

"Well if that's the case, I'm a lucky girl tonight. Thank you," she said while looking me dead in the eyes.

I've never experienced time stopping before, but in that moment I swear I was floating above my own body. I started cutting vegetables and pulling out a skillet and a big pot, and she was happy to help me prep. Her being that close to me was everything I had imagined it would be. Looking down her shirt and admiring her firm tits made me realize that all my fantasies could come true if she let them. As we cooked, we drank more. I felt like she was letting herself get closer and closer into my space. Letting me put my hand on her lower back to get around her, and her touching my arm when she laughed. It made me feel like we were having a genuine moment. As we sat at the table and ate we talked about her work and what her ambitions are, and I told her about my life and where I wanted to end up in a few years.

"I can't help but wonder," she said in a strangely sexy drunken tone. "How come you never have any girls over?"

I was taken aback for a moment. I didn't know she noticed me that much till now.

"Well, I'm a homebody," I replied when I got my bearings back. "Chicks don't really dig a guy that wants to chill at home all the times."

She laughed at that, "Maybe you're too mature for this town!" she chuckled. "Seems like everyone is a bar fly around here."

"Well, you're one to talk!" I joked, "A beautiful woman with a good job. You're the whole package!"

I was stunned by my own words the moment I sad them. How could I say something so forward like that?

She looked down and blushed at that, "Well, I have to work hard. If I don't, then this place would probably look even worse." She was looking at the table at this point, "Kyle just isn't motivated, sometimes I wonder if he even likes me."

It took a second for me to process what was happening. She's really being this open with me?

"Honestly, Samantha," She looked up at me when I said that. "I think you deserve so much more. Not that what you have is bad, but you're being put in stressful situations all the time."

She nodded in agreement.

"Can I give you a massage?" I nearly choked on my own spit as soon as I registered what I just said.

Samantha looked like a deer in headlights for what felt like an eternity. Then she pulled her hair up into a bun and got up from the table and walked to the couch.

"I didn't want to seem forward," she said. She sat on the far edge of the couch, looking over her shoulder at me "But I would love a back rub."

I took control of every cell in my body in that moment. There was no way I was going to blow this now. I sat behind her on the couch and started kneading her shoulder blades. I was mesmerized by her amazing figure.

"Wow, that already feels way better," she said as she looked back at me. "Your big hands feel so good!"

She had this look in her eyes that let me know that she was really warming up to me. I could feel the blood rush to my cock.

"I don't think I've been touched like this in years," she gasped, "You really know what you're doing!"

In that moment, I knew I had to make a move.

"Why don't you lie on your stomach?" I said with as much confidence as I could muster. "I wanna make sure I get your whole back."

Without hesitation, she scooted back into me. I repositioned, and she laid across the length of the couch. I started back on her shoulder blades and slowly worked my way down her back, admiring her body every step of the way.

"You're more beautiful than I thought," I said knowing full well I'm crossing a line. "You have such a nice body."

She giggled and looked back at me "Stop it. You're gonna make me blush!" she teased.

I kneaded my way down her back and started rubbing her hips. All I could do was imagine feeling her ass in my hands and giving it a good spank. I knew I had to test the waters and find out how comfortable she was. I grabbed her hips and pulled myself closer to her and pressed down a little harder. She let out a nice long sigh, and I think it turned into a moan near the end.

"Fuck, your back is tense," I said as I leaned closer to her. "You've been needing this for a while now huh?"

"For too long," she replied. She turned her head to look at me. "You're so good, I can feel the stress melting away."

"Ive wanted to do this for a while," I said, hoping she'd go for it. "Every time I look at you, I imagine this exact scenario."

She turned a light shade of red, "Don't tell anyone," she whispered "But I've been wanting this too."

I was shocked! I knew this was now or never. It's time to see how much of my dream I can make reality. Samantha let her body relax as I kept thinking about what I was going to do next. I just started feeling like I needed to take control of the situation right here, right now, or there was no way I was going to feel her skin against mine. In one smooth motion, I moved my hands down to her lower back, worked my hands around the area just above that beautiful ass, and moved my hands under her crop top feeling her smooth bare skin.

She didn't protest, so I kept massaging her under the shirt and kept pulling it up little by little. Soon enough, I could see her bra strap and thought that I should try going low again. I slowly worked my hands down her back again, but this time, I didn't stop at her lower back and took her ass in both my hands. It was everything I hoped it would be; firm but squeezable, and big enough that I could use the entirety of my hands on every part of each cheek. For a moment, I thought I was squeezing and rubbing her amazing ass for too long, but I felt her grind against the couch like her body just couldn't resist. In the heat of the moment, I grabbed her hips and pulled myself right up against her ass and moved my hands up to her bra strap. Now I don't have an enormous dick, just little over 5' hard, but I'm pretty confident in my ability to use it. Especially since I jerked off earlier in the day.

"Mmmmmm," she moaned, "Now this is something I definitely haven't felt in years."

She confidently rubbed her ass against my hard cock. I couldn't believe it. I don't think I could've thought of something so hot in my fantasies. Under the rush her move gave me I unhooked her bra, pulled her shirt up further, and started working her bare back. I began pushing against her to make sure she felt my erection.

"Do you like that?" I said as seductively as I could.

"I'm loving every minute." she replied now breathing slightly heavier.

I took that as an invitation to keep going so I bent down and gently kissed her neck.

"Ahhh" she moaned, slightly louder this time.

Without missing a beat, I took her hands off her back and grabbed her shoulder and waist and gently pulled back. I wanted to signal that I wanted her to roll over. She didn't say anything, just rolled over to face me. Without thinking, I kissed her. At first it was just our lips against each other's until I grabbed the back of her head and we opened our mouths at the same time, our tongues dancing in each other's mouths. I grabbed her shirt and bra and she instinctively put her arms up, allowing me to pull them off. Her large tits stayed exactly where they were without a bra on. Her nipples were the perfect size to slip into my hungry mouth. At first, I just used my tongue around her nipple, then I slightly sucked her nipple in and out of my mouth. I felt her body shiver. She pushed herself against me, completely giving herself to me. I wrapped my arms around her and laid her down on the couch as I sucked her other nipple, and I pulled my own shirt off as I sat up. Samantha was looking at me with lust filled eyes, as if she was telling me that tonight was just about her and I. I kissed my way down her belly and I started pulling off her sweatpants. She raised her hips to help me slide them off and I noticed she wasn't wearing any panties.

"Mmmm...what a dirty girl you are, not wearing any panties for me," I said as I looked up at her, the smell of her sex sending hormones raging through my system.

She started squirming, as if to tell me she was turned on by that, "Let's just call it a happy accident" she said with a wry smile.

Her pussy was just as perfect as the rest of her. The lips were the perfect size to suck on, and I could see her clit was welling up from the attention I was giving her. With one slow lick, I tasted her pussy, feeling her grind against my face. She tasted like candy, and I was immediately addicted. I focused my tongue around her clit, just circling it over and over, until I carefully sucked her clit into my mouth and used my tongue like a paint brush.

"Fuuuck!" she moaned, grabbing my head and pressing her legs against my temples, "You're going to make me cum so quuiicckk!"

I felt her body tremble as she said that, and she started bucking her hips harder so I kept my tongue moving until I felt her body shake. I heard her let out a deep and satisfied moan. I lifted my head up and saw her face filled with satisfaction, and when we locked eyes, I knew she was going to be mine in any way I wanted. I stood up and undid my pants, and without guidance, she sat up and knelt onto the floor in front of me. I was suddenly reeling in the moment, trying my hardest to keep my composure in front of the woman I've been lusting over for so long. She pulled my boxers down and my hard cock sprung up. I watched as Samantha's face filled with a hungry lust. She took my hard dick in her mouth and I felt her tongue swirling around the tip as if she were savoring the taste. I couldn't help but let out a slight groan. She took more of me in her mouth and I felt her tongue swirl all over the head of my cock. I instinctively pushed my hips into her face, while I let out a deep sigh.

"Fuuuuck, you're such a good girl," I said without thinking, "Your mouth feels amazing!"

She took my dick out of her mouth and slowly used her hand up and down the shaft, "Will you tell me I'm a good girl again, daddy?" she said with the most innocent face I've ever seen.

"You're daddy's good girl, sucking my cock like that." I moaned.

I grabbed the back of her head and moved my dick closer to her mouth, which she gladly opened. I interlaced my fingers with her hair as I slowly pushed in and out of her mouth, slowly fucking her pretty face while she used her tongue to taste every inch of me. I felt like I was going to cum right then, but I knew I needed to feel what her pussy felt like. I pulled her head back as she let out a gasp and spit her saliva on my cock.

"Lay back on that couch, daddy wants to feel you." I said in a commanding tone.

Without hesitation, she laid back on the couch, making eye contact the entire time. I pulled her legs apart and listened to her moan as I pulled her towards me in one swift motion. I rubbed the outside of her perfect pussy with the shaft of my cock, and slowly pushed into her.

"Ahhhh!" she moaned, "You're so much bigger than what I'm used to!"

She was already wet but I could feel how tight she was. Slowly pushing in I finally felt the warm walls of her pussy start to swallow me in, almost beckoning me to go deeper.

"Fuuuuck, you feel so good!" I said with a low rumble, testosterone pumping through me, "Your pussy feels like it's begging for me!"

"It is daddy," she said with a moan. "I need to feel all of you inside me!"

I slowly pushed deeper into her, pumping in and out as I did so, and I felt her pussy tighten around my cock.

"Ohhhh, you're going to make me cuuumm!" she moaned as she started squirming.

"Are you gonna cum all over daddy's cock?" I said as I grabbed her face with one hand, squeezing her cheeks together, "I wanna feel you cum for daddy"

Her face was full of emotions, and I felt her body getting tighter and tighter until she started to shake uncontrollably. That triggered something primal inside me.

"Fuuuuuuuck!" she said with exasperated breath. "You fuck me so good!"

"We're just getting started" I said as I put the back of her knees against the inside of my elbows, pushing her legs down and getting a better grip of the couch. I started thrusting in and out of her, using the full length of my cock, watching her beautiful tits bounce along.

"Ah...ah...ah!" she moaned in rhythm of my thrusts, she wrapped her arms around my body and pulled me closer.

I took one of her nipples in my mouth and started sucking it as I fucked her, squeezing the other as I did so.

"Turn over and stick that ass up for daddy." I said commandingly as I slowly pulled out of her.

She caught her breath for a moment and turned over. She stuck her ass up on all fours so I could finally fully experience the ass I've been fantasizing about for so long. I squeezed both cheeks like they belonged to me, and gave her one good spank; not super hard, but hard enough she let out a moan in response. Without wasting time I rubbed my cock on her wet pussy and it opened up and invited me in. This time, I pushed all the way into her while squeezing her hips and pulling that ass into me.