It was serendipity, really. I was just chilling at my favorite gulf-side café, enjoying my day. For 30+ years I’d been a lawyer, amassing a partnership in a firm until I just grew tired of it, and now in my mid-50’s, I’d sold my shares of the firm, my rentals and undeveloped land, and moved two states to Florida’s panhandle, having decided to go into semi-retirement.
This quiet area breeds its own type of people, and I was becoming known as less of an outsider, but still enough so that locals thought of me as one of those aloof, self-absorbed types. They weren’t entirely wrong, but I guess the two waitresses at their station didn’t know that I could overhear their conversation regarding Olivia’s desperate financial situation. And that is where the idea was born, that lead to the aforementioned moment.
Under darkening skies, I was on my way to grab some lunch when I saw Olivia, one of the two waitresses, walking and looking pensively up at the sky. She didn’t even have an umbrella, and that was serendipity. Her look beamed as she saw a customer she recognized step out of his luxury SUV, umbrella in hand. As I opened her door and got her seated, she said “Wow a knight in shining armor, thanks so much for rescuing me!” Indeed, young lady, indeed.
Olivia Reed was a real beauty, standing all of 5 foot 4 if that (163cm). She was partly Hispanic, so had raven black hair below her shoulders, pouty lips and doe eyes, and a curvy body with super nice breasts and shapely hips. She looked to be in her early 20’s (?), making her nearly 1/3 my age. Not what I had been truly looking for, but one thing the courtroom had taught me was to go with what you’ve got, and go all out.
We talked a bit as I drove, her talking all about her dead car and her money woes *same was the other night) and she gratefully accepted my offer of lunch, even mentioning that it was her first meal of the day. That was noticeable as she wolfed down her food, and I even bought her a to-go plate for her ‘friend’. It was when she was complimenting the GV80 SUV that I went with my play.
“Olivia, I have an idea, if you’re willing to listen.”
She smirked and eyed me, replying, “Umm…OK.”
“Look, I was at the restaurant the other night, and I heard that you were on hard times. In addition to I think your car, you likely have school in the fall too, right?”
She rolled her eyes and grunted an “Ugh.” Then looked at me and said, “My family is tapped, we’re locals, and blue collar at that, no offense. I’m going to have to likely drop, and just work a few years and see what happens. But yeah, I owe more than a grand on the car, rent’s behind even with a room mate, so school? Out of the question for now, especially at server pay rates.”
“yeah well, that’s my idea. How much would it take for you to be fully caught up and then also how much for school?”
“I already see where this is going,” she said quickly.
She was smart, I knew, but I noticed she didn’t get out of the car or curse/slap me, so I was still in the game. At my prompt she answered “$2K for ‘life,’ and another $3k in eight weeks.” She narrowed her eyebrows waiting for the expected brush off, but they popped up when I replied nonchalantly, “Oh, I can easily do that.”
“You…..You can?” she finally got out, as I put the SUV in motion again.
“So I turn up over the waterway, then it’s the last road on the left?” I replied. Seeing her nod numbly I continued. “I tell you what, I’ll do more than each, say…$3K for the weekend. I also have an idea for the rest of the time, but let’s get this out of the way first.”
“But…well…there’s more to it than that.” Olivia said. Seeing the waterway she said “Go straight, let’s talk.” With the rain pelting the SUV, we drove, and worked out the details. I was careful to let her know that unlike their idea of an unknown Sugar-Daddy, I was what you’d call a “known quantity” and that term resonated with her. I assured her I would be a very discreet gentleman, and the agreed number was $3K for the weekend, starting Friday early eve to Sunday early eve. She was surprisingly matter-of-fact about the whole thing, and was even agreeable to the notion that she would have to be an ‘eager participant.’ I gave her $500 for listening to me, and dropped her at her address. Friday couldn’t get here quick enough!
****
Friday arrived and I agreed that I would pick up Olivia at her address a bit early. Which was fine by me. I had a shower, trimmed nicely and shaved my balls so everything was looking good, and set off, excited to see a text with Olivia's address, and that she was ready. I took a deep breath and walked to the door. All I could hear was my heart pounding as I rang the doorbell.
The door opened, there was no one there but a voice said come in. I walked in, Olivia closed the door and gave me a kiss. I was thunderstruck;, she looked even better than I was hoping for. Dressed in very tight PVC type trousers and a tight black vest top. She had an amazing body and her outfit showed it.
She grinned and said “Well by your look I’d say you approve.”
All I could manage is "Wow, Hi Olivia, you look amazing." She grinned and pointed towards her two small bags, and off we went.
****
Olivia was quite chatty for a bit, then asked a serious question. “Why? And specifically, Why me?”
“well really, it’s just timing.” I replied. “Look, I’m a widower as you know. Been a bit more than a year now. When I am ready for a relationship that’s great, but not now.” Pointing out at an island in the distance I said “that’s where we’re headed” and turned onto the bridge, then continued. “If I’m right, then I’m 2.5x older than you, so you can’t say I exactly planned this, nor do I think this is some kind of movie, but at the end of the day, I have a want, and you have a need. This satisfies both.”
There was silence as we pulled into the gated community, and as we pulled into the drive she finally spoke. “You are a real charmer, I do say, and I also admit that you are rather easy on the eyes, even though you’re older. Yes, this is a means to end,” and then gestured all around at the beach front house, “but all in all it won’t be a bad way to go….so let’s go.”
We went up the front main stairs after a too brief tour of the first level, and what a view I had following her upstairs, my hard on was raging now. We made it over to the large couch that faced the ocean via a bank of windows. Nudging between myself and the windows, she started taking her top and trousers off, and she was standing there in lovely black matching bra & panties. Man, was she hot.
Olivia motioned to me to get undressed, so I removed everything apart from my boxer-briefs. She came close, and we kissed. She was running her hands up and down my body.
I returned the favor, feeling her lovely soft and warm skin.
She moved my hand in between her legs, rubbing both our hands over her panties, and whispered to me, "Impressed. Please impress me some more."
Olivia grabbed my cock, and I let out a soft moan. It felt electric somehow, and I could have come there and then. She pulled down my boxers, and pushed me onto the couch.
She was straight down on her knees. My rock hard cock was pointing towards the ceiling, she held it against my belly and started licking my balls, sucking on them gently. I feel like I'm in heaven. The warm feeling of each lick and suck had me moaning in delight. She started to wank me whilst using her mouth on my balls but I moved her hand away as it was going to make me cum so fast.
She stopped with a curious look and asked “are you OK?”
I replied “Hell yeah but it's going to make me cum too quick.”
With a devilish look in her eye she took the base of my cock in her hand. Slowly Olivia used her tongue all over my throbbing head, slowly and firmly sucking my cock but only down about two inches. This was all too much and I said “Shit girl, I’m about to cum!” I She doesn't even move or slow down as I exploded right into her mouth. Olivia somehow times each spurt with her movement and it felt like I'm cumming and cumming. I was literally drained and flopped back on the couch, my chest heaving looking out at a passing boat.
Olivia stayed with my cock in her mouth for a good few minutes until my hard on had subsided. It was the best blowjob I had ever had, and the weekend was still young. Olivia jumped onto the couch beside me after having a good drink of water saying, "Well that's a great way to start, with a great blow and the view to match?”.
We both laughed and I agreed.
We chatted for a bit, and she told me she was actually bi and had been living with a female lover for a few months. Her family had cut her off, and that was when the financial problems began. She also admitted that she had looked at the sites but was not impressed. When she saw the size of my dick though, she decided could be a fun weekend.
Who knows if it's true but gives me an ego boost.
She then looked at me and said "Would you like to play with your new toy? I'm yours so take full advantage."
I grinned and got her to stand and twirl for me in her underwear. Her panties were high cut showing her ample ass and the cupped her pussy incredibly well. I remove her bra and panties, and I sit her on the couch beside me. I begin by playing with her perfectly pert breasts, her nipples harden to the touch, and she moves them towards my mouth. I start gently sucking on them much to her delight. The are like thick erasers and taste great.
My hands wander over her shapely behind and in between her legs. I rub my fingers over her landing strip shaved pussy and see they are glistening with her juice. Olivia opens her legs for easier access and a better look. It's a perfect pussy, just the type I like, neat and tidy but with well-defined inner lips.
I started kissing in between her thighs and around her pussy, Olivia is breathing heavy now. I get to work on her now very aroused clit to big moans. I slip a couple of fingers in her pussy and notice she is very tight. I want her bad, but keep it up, continuing to play with her, and she must be close, because her pussy is now fully aroused and soaking wet.
“AH! I’m…I’m close to cumming!” she shrieks
I need to control this, so I stop. My cock was now solid again and Olivia was determined to get it in her mouth. I love how horny this young lady seems and really seems to want to have fun with me. I was worried things would be mechanical but not with Olivia. She was now in between my legs and really sucking my cock, changing from fast to slow, using her tongue all over my head, running it up and down my shaft, sucking my balls.
Suddenly Olivia stops, and reaches over to her bag. She has a condom in hand now and tells me, "I want you in me right now."
Hearing that makes me super horny, so who am I to argue?
She puts the condom on no problem and straddles me. She teases the end of my cock rubbing it back and forth on her soaking pussy. She slips me in and very, very slowly slips down my solid shaft. I can feel every inch of her and the heat is amazing.
“Ahhh…DAMN you’re thick.” She says
All I can do is let out a long "fuuuucccckkkkkk," as she takes me all in.
Olivia grinds me all round so I can feel every millimeter of her. Her hands on my shoulders, she starts pumping up and down on my shaft. I’m telling her to ride my dick as I tug her nipples. Her face goes to a frown, and she tucks her chin. Her hips suddenly speed up dramatically.
“This time I’m…I’m…cumming…I c-c-can’t sto-..AHHHH!” She then really picks up the pace and is fucking me faster and faster, I'm bucking my hips in time with her and we have a fantastic rhythm going, after a few minutes I feel my balls tighten and begin to twitch. As I scream I'm cumming she keeps fucking me. Once I've finished cumming I pull her in close and we have a cuddle, enjoying watching the Gulf and the odd boat passing by.
****
Again we chat for a bit and I let her know I can pay her a Grand now as agreed. She says not to worry, but does ask to actually see the cash. I have no problem with that, and walk her back to the bedroom. From a wall safe I pull several stacks of $50 bills. I let her hold them, which she enjoys. Handing them back, Olivia starts playing with my cock again and suggests it's time for round 3, as we climb onto the awesome four poster bed
Olivia really likes oral, and this time she flips up into 69 position and I start slowly using my fingers, teasing the outside of her pussy. Her moans really add to the blowjob and it now feels like she is using a small vibrator in her mouth whilst she sucks me.
Olivia spins round and, without me even realizing has a condom on me. "I want to watch you fuck me from behind, and let’s line up with that mirror." she tells me.
Olivia gets up on all fours and I slowly push my cock into her. She pushes back onto me as I thrust into her. I use my hands to play with her breasts whilst fucking her slowly. We are both watching in the mirror and it is one horny sight. I pull her head back gently by the hair for a kiss and use my free hand to play with her clit. It feels incredible and the wet smack-smack of sliding in and out of her is a symphony.
Olivia tells me she wants me to fuck her on top so she expertly changes positions.
I slowly enter her and use her legs to pull her slowly down my shaft. I start fucking her slow making sure I feel every inch of her hot wet pussy. Olivia puts her legs up and onto my shoulders. I use them to really start to fuck her fast. Olivia crosses her legs across my shoulders and the difference in tightness is unbelievable. I tell her it won't be long until I cum.
I fuck her for a few more minutes.
Then Olivia says, "I think you’re close, & I want you to finish on my face."
I pull out, remove the condom and turn to sit on the bed.. She moves between my knees while she motions for me to stick my cock in between her breasts. I do this, and she starts giving me my first tit wank. It feels so good and what a sight it is watching my cock thrusting in and out of those amazing breasts. Before long I can’t take it and dump load after load all over her neck and face. I am totally drained as is Olivia.
She grabs a couple of baby wipes, and from her bag she pulls a skimpy little satin PJ top and thong. Using the wipe and her tongue she expertly cleans me up and we spoon and cuddle in.
We’re both beat, so flipping out the light, we settle in. The first day was certainly a good one, can’t wait to see what tomorrow brings.
MathematicianReport