I wasn't looking for a new girlfriend, but I stumbled into absolute bliss
You could call me semi-retired. I'm 42 years old, and have a landscaping business that mostly runs itself these days. I'm single after my wife left a few years ago, and haven't felt the need to bring in a long-term companion.
I don't consider myself rich but I have a nice three bedroom home on 2 acres with a pool, in a nice quiet suburb north of Indianapolis. I can afford to take some nice vacations, and drive a new Honda, with a truck that's paid for by my company.
I'm in pretty good shape for my age, outdoor work will do that for you. I'm not some chiseled Adonis with movie star looks but I'm fit and always done well enough with women. You could say my wife was above my weight class, but it turned out she was a bitch as well. After 8 years, we didn't have kids, and I just didn't feel like putting in all the effort that she required. There was just no joy for me.
After checking in with my crew manager that morning I decided to go get some breakfast the local spot. After I was seated a waitress I'd never seen before comes to take my order. She's trim and has angular features and a nose that most people might consider a little bit to big.
She has a soft pleasant voice, and after she takes my order I glance at her wonderful round ass as she leaves the table. She brings back my glass of orange juice, and confirms that I don't want coffee. Never cared for that bitter drink, and I don't need the caffeine to wake me up in the morning. She tells me her name is Amy and asks if I'm ready to order.
As we interact through breakfast I noticed she says Sir a lot. I Even ask her to call me by my first name, Chris, but she continues to call me Sir. Her eyes stay looking down during the entire time she serves the table. As I finish and pay the check with my card, I give her a tip in cash. At 6 ft 3, I tower over her but I'm finally able to get her to look into my eyes as a place a $20 tip in her hand.
She must be about 5'4, and I would guess about 110 lb. Her breasts are not large, but she has prominent nipples poking through her bra and t-shirt. Her eyes are gorgeous. Dark brown with gold and green flecks. They catch me off guard for a second and I find I'm holding her hand and staring at her eyes just a moment beyond comfortable.
She quickly looks down and thanks me for my generosity. I let her know I'm a regular and that I try to show gratitude for great service. Her shoulder length dirty blonde hair falls around her face a little as she expresses her desire to serve me again soon.
The way she makes that last statement I'm not sure we're talking about an omelet. The tone in her voice gave it a deeper meaning. But maybe I was just imagining it.
I find myself eating there even more regularly over the next few weeks. After missing her on a day off, and being seated in a section that wasn't hers I start requesting her area and waiting for the table.
Over time we've exchanged a little bit of small talk and I discovered that she is not married either. Her husband passed away 8 months prior in a car accident. He had apparently not to plan well to take care of his family after his death. She had been a stay-at-home mom and was unprepared to financially provide for her family.
One morning I'm eating breakfast and Amy is serving my table. I noticed two young ladies having breakfast by themselves. They appear to be teenagers, The older girl is a redhead, that deep red color not orange. The younger girl had darkish sandy brown hair and angular features.
When Amy returned I told her I would like to buy the breakfast for these young ladies, which she responded was not necessary. I told her I insist, I know young woman should have to pay her own way. She gave me a smile and a yes sir, and thanked me for my generosity. I told her to let them know they can order whatever they want.
I can see her chatting to the girls and the big smiles on their faces as she takes their order. She returns to their table with stacks of pancakes and eggs and bacon. I didn't know teenage girls could eat like teenage boys!
When Amy returns to the table, I think her again for the wonderful service and ask her if she might possibly be free for dinner. She responds with another yes sir. I asked for her address and let her know I will pick her up at 7:00.
It's August in Indiana which means it can be quite hot and humid. When I show up at her apartment door she is in a nice sleeveless summer dress. She asked me in and sitting on the couch or the two young ladies from the restaurant. As I had suspected they are her daughters.
She introduces me to Kate who will be a freshman, and Isabella who's 2 years her junior. They come over and stand as their mother does with their eyes down as they shake my hand hello. Kate has softer features than her mother, which she must have gotten from her dad. She has lighter skin and based on the size of her tits now will likely be bigger than her mom's.
Isabella, is a couple inches shorter than her sisters 5'. She is in a white half-tee and little shorts. From her flat stomach and tone legs you can see she is an athlete.
Trying to make light of the moment, I let the girls know I will return their mom when I'm done with her. I see smiles with the yes sirs.
Walking Amy to the car I noticed her ass in the little dress. She is obviously in a thing as her ass moves deliciously when she walks. I love a great ass! It's even more impressive after two kids.
As we talked through dinner, I began to form a picture of her life before her husband's death. He appeared to be a strict and domineering man, and based on her demeanor she was comfortable in that relationship.
We strolled through the downtown of the village where I live, and I placed my hand on her lower back just above her ass. As my fingers laid against her soft dress I noticed I did not feel the expected waistband of her thong. I slid my fingers down just a little and still felt nothing. With her nipples poking through and the side of her breast I could see in her sleeveless dress, it appeared she was not wearing anything underneath. I felt myself stiffen up.
I'm now thinking this night will go a little differently than I expected. I asked Amy if she would like to go to my house for a nightcap. She gives me another Yes Sir, and adds that it would be nice.
As I open the door for her and let her into my car, her dress rides up where I can nearly see her uncovered pussy. She has nice tone calves and thighs that I hope to have wrapped around me soon.
I pull into my hidden driveway through the trees and into the garage. We go inside and she looks around and comments at how lovely my home is. I've been a bachelor for 3 years, but I don't live in a bachelor pad. I don't hang with a big group of bros or anything like that. I have a small group of friends and most are married.
I fix a couple of strong cocktails and give her one. I walked to the living room and sit in my chair leaving her standing in front of me. I decide to find out how submissive she really is.
"Your not wearing anything under that dress, are you Any?"
She quietly answers No Sir as she looks at her feet.
"Would you like to take it off for me?"
"Yes, sir", she says.
"Do it", I say with a more demanding tone and lust in my voice.
She gracefully slides the dress over her lithe body and drops it to the floor next to her. She stands before me and only her heels and a delicate gold chain around her neck. Has she stands looking at her feet, I take my time looking at her body. Her breast seem firm and maybe a small c cup with her large stiff nipples. Her stomach is mostly flat and she is neatly trimmed with her area around her labia shaved.
The lips of her pussy are full and thick and I can see her clit protruding nicely at the top. I can see the dampness of her excitement. She is trembling as she stands in front of me. I haven't even kissed her yet and the first intimate contact we have is me sliding my index finger along her damp lips, flicking her clit lightly at the end.
Her knees buckle slightly and I hear a deep moan emanate from her chest. I asked Amy how long it's been since she had sex. Apparently two days before her husband died was the last time she has been touched sexually.
"Have you made yourself come since then?"
She tells me no, because she was not allowed to orgasm without permission.
"Have you been lost without a Sir? Would you like me to be that person?"
"Yes sir, very much." She moans.
" I need you to demonstrate what I can expect from my new slut, if that's what you want to be."
Without a word Amy kneels at my feet and starts removing my shoes then socks. I noticed she places everything neatly to the side. She undos my belt and removes my pants, folding them as she goes. Next she slides my boxers off.
She slides her hands up my thighs and softly massages my balls and shaft. I hear moan with desire as she looks at my hard seven inches. I'm not overly long, but I am thicker than most, or so I have been told.
"May I Sir?"
" You may. And consider this an interview, slut."
"Let me know if I am not pleasing you, sir."
With that she leans over and gives a long lap from under my balls to the top of my shaft. She moves back down to my balls and spend a few minutes gently sucking and buzzing them. She is making "mmmmm" noises as she goes apparently enjoying her work. Her hands stay busy with my cock. While licking under my balls she slides her hands under my knees and lifts to pull me forward and raise my hips. She wants access to my ass. Good girl!
She takes time rimming my ass forcing her tongue deep. She's very good at this! I could easily let myself cum this way, but I resist the urge. After several blissful minutes she finally moved to take my cock in her mouth. She takes a long lick up the shaft and takes the head in her mouth. She is drooling on my cock and smearing it with her hands making me slick. She gets up higher on her knees and starts taking me deep. It's takes some effort on her part and her mouth is stretched tight around my thickness.
Eventually she is taking my whole cock deep into her throat with grunts and moans. She really loves what she is doing, you can feel the sexual excitement emanate from her.
After a couple of minutes of me fighting a losing battle against flooding her mouth, she leans back and asks, "would you please fuck my throat, Sir?"
"That sounds lovely, slut!"
"No need to be gentle, sir."
And I am not. I stand for leverage, and slide my cock in her mouth. She brings her hands, but I slap them down. Amy dutifully puts them behind her back. This isn't new to her. Knowing that, I take her head in my hands and slide in deep. After a couple of probing strokes, I start being more forceful and soon I am fucking her face hard. I can hear her grunts and glub, glub as I push deep. She is drooling onto my balls. When her eyes go wide and her face is deep crimson, I pull out and let her gasp for breath.
I have been on the edge for a while, as this blowjob has gone on for half an hour, so I am ready to fill her throat. I pull out again and tell her to take a deep breath because I'm not stopping until I cum.
"Thank you, sir. Please, feed me!" She pleads and gasps.
I push deep again and grabbing her hair tight start pounding her face hard, her nose crushed into my pelvis and my balls slapping her chin. It doesn't take long before I push deep and fill her stomach. It is the most satisfying orgasm I've had in a long time. I pull back at the end to leave some on her tongue so she can taste me as well.
I drop back in my chair and she dives back on my cock licking me clean and slurping up the excess saliva leaving me mostly dry by the time she is done. I am enjoying the afterglow of my orgasm as she gently sucks on my softening cock.
"Stand." She does so as quickly as she can after being on her knees for forty minutes or more. Her thighs are wet with her desire and I run my fingers up her leg and across her pussy again. She moans in need, but she is going to have to wait. I pushed soaked finger in her mouth and she hungrily cleaned of her juices. She was soaking wet. This girl loves to serve.
"I think we should call it a night. If I choose to accept your service, I will contact you tomorrow."
The despair and need to cum shown brightly on her face. It was flush and her heart was beating fast in anticipation of a orgasm that wouldn't be coming. She groaned internally, she needed it bad, but not tonight. I wanted to reinforce the idea that my pleasure will always come first.
I drove her home with a hand on her knees, rising her tension a bit more. I opened her door, but didn't walk her in or kiss her goodnight. I wanted her fear and anticipation to be nearly unbearable.