Yes, Daddy!

Disclaimers:

This is my first submission, so please be kind. I'm open to constructive feedback, and as I've never done this before, I haven't made contact with any editors from this site, so bear with any grammatical or spelling errors. Hopefully, further submissions will be forthcoming.

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I was mesmerized from the moment I saw her. Skin like caramel, tight braided hair, make-up and jewelry done tastefully to perfection; she was stunning. Her large, brown eyes seemed to peer straight into my soul, and it took everything in my power not to give away my immediate crush.

I've never pursued a coworker before, both because it can lead to an uncomfortable work environment, but also, because I've always felt that women at work are there to make money, not to get hit on. It didn't stop me from introducing myself, though! Her name is Tiffany, she's 22, mixed-race, and a bit of a bigger girl, but she carries her weight nicely, and she knows how to dress for her body shape. Here's where I start to run into some issues. I just turned 50. I'm white, with long, gray hair and "pretty" blue eyes. I've got the "Dad bod," and I'm carrying about 30 pounds more than I would like, but I'm in good physical condition, due to working in a restaurant and being a military veteran. With Tiffany being a server, and me working in the back-of-house, we only run into each other occasionally throughout a shift, but every time we do, it's always pleasant.

Tiffany's behavior with me was typical of a new hire at first, but eventually, I started to pick up on signs that she might be interested in being more than a co-worker. It was simple things like, coming to me to ask questions, listening to my Dad jokes and laughing (or groaning, as appropriate), or giving me a good-natured ribbing when I was stoned. I soon realized she was paying as much attention to me as I was to her. Needless to say, she started creeping into my fantasies, as a lot of my younger co-workers often have, but this time, there was a level of intensity I hadn't experienced in a long time.

I let this continue for a few months. I was highly aware that it wouldn't be appropriate for me to make a move, and I couldn't really be sure that I wasn't mis-reading the situation. Blame it on my own insecurities, but I just couldn't imagine that she was crushing on me the way I was on her. I hadn't been with a woman in over a year, and I was lonely, so I figured I would be satisfied with the common flirting that restaurant people are prone to do, and be grateful for it.

Recently, some of my other back-of-house co-workers came in to work and were raving about Tiffany's singing voice. Apparently, she likes to perform karaoke at the bar nearby where a lot of our local industry people hang out. As I'm mostly a homebody, and significantly older than my "peers," I tend not to join them, as I don't want to make them uncomfortable with my presence, but they all were raving about Tiffany, and told me I just HAD to come out to hear her sing, so I agreed.

The whole day of our planned get-together, I did little things to get myself ready. I cleaned my house, cleared out the trash in my pick-up, made my bed with fresh, clean sheets, and whatnot. I kept telling myself not to get my hopes up, that the chances of something happening with Tiffany were next to zero, but I still couldn't help myself. I was titillated by the thought that I might get this young, beautiful, sensual goddess into my bed, and I didn't want there to be any distractions if it came down to that.

That night, I showed up a little bit before the group. I had a couple of cocktails to relax, as I don't do well in crowds or group social situations, and settled in for the evening on the patio. The next person to arrive was Tiffany, and I couldn't have been happier to see her! She had on a short, white dress which contrasted against her caramel skin with a lace-up front that showed off her ample bosom, her cleavage playing peek-a-boo through the strings, and the bottom of her thighs tastefully on display, causing my imagination to run wild at the thought of what might be further up, hidden away from all but the luckiest few. She tapped me on the shoulder to say hi, and dropped her purse off with me, while she went in to get herself a drink.

When she came back, our conversation was smooth and natural, we talked about work, but not too much, we talked about our sex lives, hers being far more interesting and recent than mine, and we shared a couple more cocktails, with her introducing me to her favorite, an amaretto and coke, of which I quickly became a fan. Eventually, the rest of our group showed up, having already gotten the party going elsewhere, and the night picked up from there. Tiffany got up and sang a beautiful rendition of "This is a Man's World," her tiny, cute speaking voice coming out now in big, powerful belts as she was obviously feeling the emotion in the song. I had to admit, if the night ended after that, it still would have been worth coming out.

Our friend group did as they usually do, they spread out and mingled with people they knew, but Tiffany came back to sit with me, and our conversation started turning a little more serious. She was looking at me now, not with the eyes of a good conversation partner, but with eyes that screamed at me that I should do something. At this point, I was drunk, and a little high, but I knew that I needed to make sure that we were on the same page. I didn't want to be a creepy, older man, taking advantage of a younger woman.

We acknowledged that there was a certain, mutual chemistry between us, and the cat was out of the bag. My only problem was that I knew I should not be doing this. Not for my own consideration, but for hers. I then proceeded to talk my way out of getting laid that night. Tiffany is smart, and emotionally mature enough to understand my concerns. She took it all in stride, and we agreed that we shouldn't proceed any further than the harmless flirtation we had been sharing.

Closing time rolled around. At this point, everyone else wanted to go to the local dive bar that stayed open late for industry people. I still felt up for more, so I agreed to go, and Tiffany came along with us. I grabbed a ride from someone, and she drove her own car. It was only a few blocks, and before I knew it, I had a double shot of rum on the rocks in my hand. A mistake I would pay for later.

I made sure to socialize with our group, and even ran into other people I knew from around town, but eventually, I ended up talking to Tiffany again. Once again we were flirting with each other, only now it was a game of calling each other out when we were doing it. Tiffany has a habit of running her tongue across her teeth when she's thinking, and it's so sexy it hurts. I apparently bite my lip when I'm thinking about inappropriate activities, and she made sure to point it out.

Once last call was announced, everyone started scattering for their cars. Couples each left together, and I walked Tiffany to her car. Even at this point, I had every intention of being a gentleman, but as we were standing by her car door, we locked eyes one more time, and I said, "We're about to make a bad decision, aren't we?"

She said, "You're the one who said we shouldn't, and I understand and respect your reasons."

I reached out to touch her face, as I told her, "It doesn't change the fact that I want you."

As soon as I caressed her lightly freckled cheek, I heard the sexiest whimper escape her lips, and I knew that I was going to do anything she wanted that night. I pulled her face to mine, gently kissing her full, dark lips, and her whimpers intensified to moans immediately. She pushed her tongue to mine, and we shared a passionate, deep kiss, as though our mouths knew instinctively what the other person needed. I pulled her body to me, her smooth skin a delight to the touch. Her kisses intensified, and I realized that her entire body was sensitive, unexpectedly responsive to the slightest stimulation. I couldn't wait to caress her and kiss her all over.

Our passionate kissing only broke because we needed to go somewhere to complete the business at hand. I asked her if she wanted to come to my place, or go to hers, and in between heated breaths and tongues, we agreed to go back to mine. At this point my hands were freely roaming over her back and breasts, grabbing her by the neck, or gently caressing her arms. Coming up for air now and then, she would moan, "Oh, shit" or "Oh, fuck" before coming back to my eager mouth. Finally, we disengaged as she told me to get in her car.

On the way to my place, I slid my hand over her thigh, and she parted her legs for me. I needed no further invitation, and gently brushed my fingers against the front of her panties, pleased by the heat and wetness I discovered. When we stopped for traffic lights, I would apply more pressure, causing her to lean back into her seat and press forward with her hips, grinding as hard as she could. When the light would change, I would back off my pressure, and tell her where to go to get to my home. The sounds she made would have likely had me cum before we made it there, but the liquor in my system was preventing that.

When we arrived, I reluctantly stopped teasing her long enough to get us in the house. I mentally high-fived past me for cleaning up like I had. We made it to the bedroom and laid down, no more questions, no more hesitation, no more concerns; just pure, unadulterated lust. Her kisses were like lightning, her whimpers and moans like music, her body writhing at my touch. Her lips and skin tasted sweet like the amaretto we had been drinking.

I started tugging at her dress as she straddled me, grinding my cock with all of her might. She lifted it over her head, and I immediately reached for her bra. I needed to see her breasts, which had been tantalizing and teasing me all night. As soon as her breasts were free, I grabbed as much as I could fit into my hands, leaned up and sucked her nipple into my mouth, getting the response I was looking for.

"Oh, fuck!"

'Oh, fuck' was right. Her responsive body began succumbing to my mouth, my hands, and the partial erection I had, which she had never stopped grinding against. Mentally, I had not been so turned on in a long time. My brain was on overdrive. I kissed her skin from her nipples to her neck and back again.

Tiffany leaned down to my ear and whispered, "I want you to fuck me, Daddy." I was new to this type of play, but I found it hot. She looked like a porn star, begging for a big cock.

I'm not a porn star. I'm decidedly average in that department, but a little on the girthy side. Unfortunately for me, the alcohol at that point interfered enough to keep me from getting fully erect. I knew this was going to be an issue, but I didn't care. I wanted to taste Tiffany, I wanted to see her body, kiss her everywhere, suck her everywhere.

I told her that I was going to need a little "help" from her, and did she want to make me hard with her mouth? She nodded at me while pouting those beautiful lips at me. I asked her if she wanted me to taste her first, and she said, "Uh-huh" before rolling off of me and onto her back, sliding her panties off in one quick motion.

I wasted no time, still fully clothed, and leaned down to enjoy my feast. I started by kissing her mouth, moved to her neck, and down to her breasts. The sounds she was making from just this simple contact were driving me insane, and they only served to egg me on. I continued travelling downward, trailing kisses along her stomach, from one side to the other, moving slowly further to my target, the source of heat and wetness I had already felt in the car.

As I neared her vulva, I made sure to gently tease her by placing light licks and kisses on her thighs, above her mons, and along the joints where her legs met her intimate skin. By now she was squirming with her eyes closed, swearing at me sexily, encouraging me.

I settled in and got comfortable. I traced the outsides of her labia with my tongue, placing light kisses on her outer lips. Occasionally, I would lightly swipe my tongue across her hooded clitoris, receiving the gift of more moans and whimpers for my efforts. As I ramped up the attention I paid to her clit, I also began exploring the other areas of her sex, licking from the top, down to her perineum, and back again. Each time I would make another pass, I asked her if she wanted me to go further.

"Yes, Daddy!"

My tongue grazed the entrance to her back door, and I could hear the sound of her lungs inflating as she sucked in a large breath. I knew that I was going to have so much fun with her at this point, but I wanted to take my time. I gave her puckered butt hole a couple more light licks, before I aggressively slid my tongue all the way up to her clitoris and began sucking her off in earnest. She grabbed my head and pressed me into her, and I slid a finger into her wet, warm pussy. I hooked my finger so I could touch the ridges along her g-spot, her walls undulating with her hips as she fucked my face for all she was worth. I continued giving her a good tongue lashing, alternating between heavy licks and sucking. When I came up for air, I pulled my finger out of her sopping wet slit, and gently caressed her asshole with it.

"Do you want me to play back here, too?"

"Uh huh!"

"Good girl," I grunted, as I gently began pressing my slick finger into her most intimate place. She relaxed into it like a seasoned professional, and my finger disappeared up to the second knuckle. I couldn't believe how lucky I was. I began to attack her clitoris while I finger-fucked her ass. Her moans and cries became more amplified, and I asked if she was going to come for me. I locked eyes with her, my mouth closed over her clit, and she turned those beautiful brown eyes to me.

"Yes, Daddy, I'm going to cum for you!"

"Cum for me now!" I ordered.

And she did. Her moans stopped and turned into a high pitched whine, her legs clamped around my head, her hips bucked wildly as she ground against my face and finger, my hair knotted in her fingers as she pressed into me and pushed me away at the same time. I did everything I could to keep up the pace and pressure through the entirety of her climax, prolonging her pleasure as long as she could stand it.

I have never been so proud of my oral skills as I was at that moment. The tiny little shudders from her post-orgasm telling me she would remember that one for some time. I kissed my way back up her stomach, lightly, caring for her in the afterglow of her orgasm. When I reached her mouth, she kissed me hard, her tongue telling me she wanted more.

"I need you to fuck me!"

It was at this moment I knew that I wasn't going to be able to fulfill that need. The alcohol had done its damage, and I was no longer even semi-erect. I told her I would need help, and that it might not happen, but she pushed me over onto my back, and bent down to take my partially inflated cock in her mouth. The sight of this goddess with her lips wrapped around my member would normally have me raging, and the sensations I was receiving were top-notch, but by now I had enough past experience to know my situation.

I praised her skills, grabbing her by the head and helping her along. She got me back up to half-mast, and sat up to mount me, but she was so tight, and I wasn't hard enough to force my way in. I made peace with the fact that tonight wasn't going to be about me, so I told her to sit on my face and suck me some more while I picked up where I had left off earlier, enjoying a 69 for the first time in forever.

She was so understanding, my whiskey-dick not the first time she had experienced one. She told me it was okay, and I told her I wanted her to lay back down. When she was once again comfortable, I went back for seconds on her clitoris. She tasted so good, like a vanilla scented candle for my tongue. This time, I licked her for a longer time, but she was still so responsive, I knew that she would be multi-orgasmic. Dipping my tongue into her vagina, I felt her clench her thighs around my ears. I didn't linger, as I had a new target in mind. I proceeded to give her asshole a long, deep lick, pressing against the outside ring.

"Ooooh, fuuuuck!" was the response I got. I pressed my tongue even harder against her tight sphincter, and she relaxed enough for me to push about half an inch of my tongue into her. By now, I knew I had the holy grail of fuckable women in my bed. There were no limits with Tiffany. As I tongue-fucked her butthole, I traced my fingernails up and down her thighs.

"Spit on me!" she commanded, rather unexpectedly. I know how to do what I'm told! I brought a mouthful of saliva up to my lips and smeared her butthole and perineum with it. She moaned heavily and said she was close to cumming again.

Having already witnessed how powerful her orgasms are, I knew what I had to do. I wet my finger with my saliva and gently, but firmly, pressed it back up her butthole to the second knuckle, while clamping my mouth over her clitoris and sucking the life out of her.

What followed was a repeat performance of Tiffany riding my face like I was an amusement park roller coaster. Her orgasm hit her hard, and she clamped her legs around my head while she bucked and twisted. My finger plowing into her backside as if I was digging for gold, my mouth working her clit like it was my day job. When she finally came down off her high, I didn't move from my spot. I continued to gently kiss and lick around her thighs and stomach. We talked some, her beautiful face and eyes telling me she wanted more, and I was going to oblige her. Eventually our pillow talk turned into lusty moans and grunts, me encouraging her to enjoy herself to her fullest, that I would do whatever I was able to do for her. After a few moments she told me to gently, slowly finger her pussy while she rubbed her clit.

Watching a beautiful woman touch herself up close is an erotic experience. Sharing that moment with her, encouraging her to cum once more, I pushed a second finger inside her, reaching even deeper. I found the soft tissue behind her G-spot, and began hooking my fingers firmly into her, attempting to coax one more orgasm from my new favorite playmate. As she got closer to cumming, I moved my entire body up from between her legs.

"Look at me, Baby Girl."

She opened her eyes, stared deeply into mine, and I began to forcefully finger fuck her with the last of my strength, not breaking eye contact with her.

"Oh, FU-U-CK!" she tried to yell, as I pistoned my fingers into her while she rubbed her clit. She locked her legs around my waist, and I kept jack-hammering into her with my two fingers. She started reaching above her head with her free hand.

Then it hit her like a ton of bricks. She stopped rubbing her clit, and with both arms tried to push off the wall behind her head. She looked like she was trying to escape the most powerful orgasm of her life. She was looking around for anything she could grab, anything that could help her in that moment, but I knew she was also loving the experience.

Eventually, Tiffany calmed down. I could tell she was fully satisfied, and we were still giving each other loving pecks and licks, but with much less intensity. Gently, I disengaged from my new lover, not caring that I was older than her, not caring that I hadn't had my release, just happy with the fact that I had a new playtoy, one that I couldn't see myself ever getting tired of.

After we cleaned up, she drove me back to get my truck, and we parted ways with one more kiss. It was 5am, and I realised I'd been up almost 24 hours. I got back home, texted Tiffany good night, and drifted off to sleep, not sure what the coming days at work would be like, and not caring one bit.