A good friend of mine referred me to this great Italian restaurant in a city about 3 hours from where I lived. I asked him, “What the hell makes this place so special that I would be willing to drive 3 hours?”
He told me the service was worth the trip alone, and the food was even better. I took some time to think it over and a few days later I called to make a reservation. The person on the phone asked my age, and if I preferred smoking, non-smoking, or the cigar lounge.
I wondered what the age question was all about and she said that there was a minimum age limit for their restaurant, which I was able to meet. I then told her I wanted to be seated in the cigar lounge for cocktails, but non-smoking while I ate. She then asked if I would like a private table or a table near the windows, which overlook the city (the restaurant I found out is in the heart of the city, and is on the 10th floor!).
I was amazed at all of this, considering my friend never mentioned any of this. I was beginning to wonder how much this damn food was going to cost me if there was all this fuss about seating arrangements. The lady then began asking me questions about what I would like to eat. Now keep in mind I was making reservations for about 2 weeks or so later, and she is already taking my order! I explained I had never eaten there obviously, and I wasn’t sure what there was, let alone what I wanted.
She kind of giggled and told me no problem, that is what she is there for, to get me situated so when I arrive I will have the ultimate dining experience from start to finish. I slowly relaxed and thought wow no wonder he said the service was worth it alone. I went along with her and I ordered an appetizer, which was a bowl of fresh clam chowder, my entrée was the filet mignon with lobster tails, a vegetable, my dessert was a chocolate raspberry tart with fresh raspberries to accent with chocolate drizzled all over it. Not a bad little meal I thought.
Now my next fear was the cost. Fortunately it wasn’t too bad, only $150.00 for the meal, cigars, cocktails, and tip all included in the flat rate. I was told it was the same price regardless of steak, or hamburger meat. Glad I ordered the good stuff I told her and we both laughed. I thanked her for her time, asked her name, which she told me, was Olivia, and hung up.
When I hung up the phone I was in a daze over making a 150-dollar dinner reservation, and that I was going alone! “Shit!” I exclaimed. “Now what the hell I am going to do? Cough up another buck-fifty for a date?” I quickly called Olivia back and asked if there was an additional charge for a second guest, which is if I could find one. She sighed kind of sweetly and said no the charge covered parties of up to 4 so bring anyone I desired.
She suggested that if things didn’t work out as far as finding a dinner guest that the cigar lounge was usually well “stocked” with ladies as long as I didn’t find 40-60-something, cigar-smoking women unattractive. I felt a stirring in my jeans at that moment. I stammered out that no, in fact I would most likely show up alone if that were the case. We both laughed and hung up.
The next morning I went downtown to pick out a new outfit for my night out. I got it all. The shirt, tie, jacket, slacks, shoes, even matching socks that corresponded with the tie and jacket.
It was the morning of my dinner out of town experience and I decided to go all out (especially since I was shooting away 150 bucks for my dinner alone.), and get a fresh haircut, shave, and manicure. Now I am a blue collared kind of guy, and to me this was the most extravagant thing I had ever done. I figured we only live once and try something overzealous and live a little.
“Holy shit!” is all I could say when I arrived in front of this museum-esque building. I got out of my car and gave the keys to the valet and handed him a ten-dollar bill. He thanked me, and said, “Mr. Smith, you will be going in the foyer and turning right and taking the elevator marked C1C.”
“Alright,” I said and went in and followed his instructions. Now the outside looked like it cost a couple of countries worth of national debts to fix this place up, but inside was very modest and comfortable.
Once I got up to the restaurant I approached the Hostess and asked if she was Olivia, and she told me Olivia was off for the evening. She introduced herself as Natalie and escorted me to the cigar lounge. Natalie told me it would be about 30-45 minutes before my dinner would be ready so to relax and enjoy myself while I waited.
As I was strolling around the lounge checking out the décor I noticed an attractive lady sitting on a leather couch in the back of the room reading a novel of some sort. She was short in stature, probably in her late forties. She had a silver mane like I’ve never seen before on a woman, which came down and rested on her very full-sized breasts. It shimmered from the soft lilac lighting in the lounge. She wore glasses that I thought made her astounding to look at. She wore a full-length dinner dress that was showing plenty of her attributes in all the right places.
Her neckline was exposed to show off a soft set of pearls, and the slit on her dress went up to almost her hip it seemed. I could see the hemline on her thigh high stockings. Her thick legs looked delicious. For a full-figured woman she was breathtaking. Her makeup was sensual, and those full pouty lips were as crimson as they could be. They had a glisten to them that would blind you if in the light. I approached the bar and asked the waiter to fix me a 7&7 double, and if he could tell me what the lady in the corner was having that I would like one of those, too.
He told me that she was drinking a glass of Chablis from 1972. He served the drinks and I walked over to the couch area, and excused myself and handed her the Chablis. She looked up at me over her glasses and smiled, then thanked me. She was kind of quiet and reserved. I looked over to see a fabulous selection of cigar burning in the ashtray next to her and asked if she cared that I sit and join her. She graciously slid over slightly and I accompanied her. Before I could get settled, I decided to go ahead and make a selection for a cigar. I apologized for my nervousness, and when she giggled I knew who she was instantly.
“Olivia?” I asked.
“Yes, Mr Smith it’s me.’ I hope you don’t find this to be inappropriate, but when you told me you would be coming alone, I called Jack (our mutual friend who told me of the place) and asked a few things about you.” My jaw was in the floor at this point. “Um, no why would I find this inappropriate, and if I may ask; what exactly did you two talk about?”
“Oh a little of this and a little of that.” She said with a devilish grin in her eyes. I told her to call me James, and that I would be right back, I needed a cigar. Before I got up from the couch she placed her hand on my arm and asked me to stay seated. She reached into a tabletop humidor next to her and removed a cigar already punched and told me it was for me. This lady did her homework. She knew exactly by brand, ring gauge, and style of cigar that would enjoy smoking. She handed me a Bucanero Maduro wrapped Churchill 50-ring stoagie and followed up with a fancy looking torch lighter that resembled a miniature wine bottle.
I told her I was not used to a lady lighting my cigars; it was usually the other way around. Softly she said that maybe later she would let me light her up. Before the two of us realized it she quickly added that she was referring to her cigar, and to forgive her. The wine was playing naughty with her. I told her no need for forgiveness that either way, I wouldn’t mind. We both smiled and took a moment of silence. I asked her what she was reading. She told me just some half-porn romance novel. “I was nervous about seeing if you looked as good as you sounded, and Jack described you to me so I figured if anything didn’t go right, I always had my trusty “backup plan”.” We laughed hysterically.
“Anything Jack tells you about me is a 50-50 deal.’ It’s usually 50% false, and 50% exaggerated,” I told her. Olivia said, “Oh I don’t see it that way at all. I think Jack understated you.” I could feel myself becoming somewhat embarrassed by her flattery. Olivia was a sweet, soft-spoken lady. I found her company soothing. She was a very intelligent lady who seemed to have a vast knowledge of a lot of different topics.
After about 20 or so minutes of more small talk, the Hostess returned to the lounge to tell me my dinner and table were ready, to follow her. I asked Olivia if she would care to join me for dinner. She smiled, and took me by my arm and said she would love to. We were seated in a private corner of the restaurant away from most of the other guests. Four strong burning candles and one soft light bulb overhead illuminated our table. Our waiter brought out the appetizer and a wine list to see what, if any wine we would like to have with our meal.
I was embarrassed and asked Olivia to make a recommendation, as I was not real versed in wines. She suggested a bottle of what she was currently engaged in, and so it was ordered. As the meal progressed we began to learn a little bit more about one another, but on a more personal level. Olivia told me she was proud to admit to being a 49-year-old woman, who had never married or had children. She enjoyed living in the city because there was so much to do in the city, and she couldn’t for the life of her leave it. I also learned she not only was the Reservations Manager, but she worked part time at the Museum of Fine Arts, and Culture as an appraiser for the auction department.
She then made a joke about how several buyers have tried to place a monetary value on her. I told her that if that was the case, I should probably warn her that I would never be able to afford her after tonight. She blushed and told me if I really wanted her that bad, all I had to do was ask. I looked her dead in her jade green eyes and asked her flat out, ” Well then could I ask to keep you company throughout the evening, even after dessert?” The smile and the intense reddening of her face told me she was comfortable with that. She whispered in my ear, “Only if I can be your dessert.” I have never tried to eat so fast in all of my life!
Olivia slid closer to me at the table and I felt her place her hand on my leg and give it a slight squeeze. She said, “How about skipping the rest of the meal, join me back in the cigar lounge for a quick smoke and maybe a little something extra.” The first thought that came to mind was, “Sure, but you’ll have to twist my arm a little harder.” Her perfume was incredible, and it wasn’t until that moment that I felt a surge of sexuality coming from her. When I watched her walking towards the lounge I took a moment to absorb every inch of her fullness. I am guessing about 250-275 pounds on a 5’2″ frame (5’5″ in her heels).
I couldn’t help but blurt out, “Outstanding!”
She turned and looked at me and asked, “What’s outstanding?”
My reply was, “You are, from head to toe, and everything in between.” She stopped in her tracks waited for me to catch up, and when I did she took me in her arms and pressed her firm, full body to mine, then kissed me like a woman kisses a man on their wedding day. Long fulfilling kisses of passion. Our tongues took their own tour of each other’s mouths while we held each other tightly. We broke long enough for her to suggest we grab a couple of smokes, then to follow her.
After we made our choices we proceeded to the elevators and she selected number 22. She winked and said, “My apartment is up here. It’s one of my perks for the job I do. Instead of a lavish salary, I get a place here in the building.” I was impressed, but then I wondered how many other “dates” she had met and entertained before me. As quick as that thought came in, it went out because here I was a 30-year-old guy who has a dating life not worth mentioning walking behind one exquisite full-figured (not to mention very sophisticated) mature lady who would make a blind man see.
When we arrived at the 22nd floor, we took a left and walked down the hall to a door with a security guard outside the front and she said, “Hello Paul, I’m in for the night and this is my friend James. He will be staying the night so have the Valet move his car to the garage, and have downstairs bring up another bottle of Seagrams 7, please.”
“Yes, Ma’am,” Paul announced, and was on the phone instantly.
Once inside the room we were like savage animals pulling at each other’s clothes. If we weren’t kissing, we were removing articles of clothing. If we weren’t doing that we were grabbing one another. I could really get a sense of her animalistic prowess the minute she released her massive breasts. They were so fucking big, yet they were upright and the nipples were very plump. Her aureoles were as big as my hand for Christ’s sake!
“Oh yeah” she cried out as I took one of her grape-sized nipples in my mouth. “Yes baby, suck on Livvy’s tits. Oh god damn that feels so good.” I massaged her other massive boob while chowing down on her nipple. I could feel her freshly manicured nails drag across my waist fumbling with my belt and zipper. Once she dropped my pants, she then dropped to her knees. She placed her face against my lap and inhaled my crotch scent. My cock was aching to be released from its captivity of my boxers. Olivia reached inside and grabbed my hard shaft and looked up at me and smiled from ear to ear. She rolled her tongue across her luscious lips as she took my boxers down and began flicking the pre-cum soaked tip of my cock with her tongue. She cupped my clean-shavened balls while coating my cockhead with her lipstick stained saliva. She worked my shaft up and down feverishly while jacking my balls all over the place. I could feel my nuts getting tighter as she began to suck me for all she was worth.
Her head bobbed up and down wildly as I began spitting one thick shot after another into her mouth, coating her throat with my jism. She slurped and lapped at it as if it were her last time ever. I cried out, “Oh Jesus Christ! Oh yes, eat it all, baby. Eat my cum, it feels so fucking good shooting into your throat.” Olivia was a master. She got up from her knees and wrapped her thick arms around me and began feeding me the leftovers of my seed. I thought this was the sexiest thing I had ever experienced. She pushed me back onto her couch and told me to light up a smoke while she stripped the remainder of her clothes off. I had a puzzled look on my face thinking, was this it? Was this the end of the sex?
It was when she dropped her dress to the floor that I was able to truly appreciate this super-sized Madonna. Her thighs were almost as big as my waist. She was wearing thigh-highed stockings without garters. Her calves were so strong and full looking. I knew this woman would be on all fours tonight. She kicked her dress across the room. She wore an ankle bracelet of several little gold charms. Standing there in just her stockings, heels, bracelet, pearls, and her panties (which had a wet spot the size of her fist in the front), she just looked at me and asked, “See anything you like?”
My cock was already hard, and this time I think it got bigger than it normally has in the past. “Well judging by that thick knot between your legs, I’ll take that as a yes,” She naughtily answered her own question. I told her to walk slowly towards me so I could inspect her nakedness in motion. She took her time stopping after every step to make sure I could take it all in. “Damn, what an incredible sight you are, ” I told her. She got to me and straddled my lap, took the cigar from my mouth and took a draw. She inhaled it deeply, blew her smoke in my face and asked if I was still hungry for some dessert. I reached around her and caressed her back and waist in my arms.
I could feel her heavy breasts as her nipples stabbed my chest. I took her tongue into my mouth and nibbled on it as I slid my hands down her belly and into the lining of her damp panties. Her musky scent was intoxicating, as the room now smelled of lust and fever. My hands slid the hem of her panties down around her wide hips and looked in amazement at her round (what I like to call the pouch; the part that hangs over the pubic region) tummy as it secretly hid her sterling silver, and very neatly trimmed pussy hair. She only had a star shaped cropping above the top of her channel, and all below was as smooth and clean as glass. Her lips were very defined, and I could see an abundant amount of crème built up in her crease.
I knelt down on my hands and knees as I assisted the panties to the floor and lightly with my tongue started at the nape of her neck, and traced little circles all over body down towards the silver mine. I took my time teasing both of her tits. I would flick her nipples and bite with my lips on them. I was driving her crazy as she sighed out loud in a stuttering breath. My hands kept working her large body like kneading fresh dough. I would grab a handful of her massiveness and just grunt in bliss at the feeling of all of her in my control. She squirmed like a little girl when I licked along the underside of her breasts. I continued my way down towards her big belly, still using only my mouth and hands, but never together in the same area.
As I was kissing her flesh, I would manipulate her thick thighs with my palms in a spreading fashion. Olivia parted her legs willingly as I progressed further down her body. As I approached near her southern region, I became overwhelmed by her scent, and the feeling of her controlling my head in her hands was absolutely astounding. She cried out, “Please for the love of god, quit teasing and eat Livvy’s wet cunny! Run your tongue in my slit, baby. Jam your fingers in my wet pussy while you suck on my big clit!”
This sophisticated business executive was now talking like some blue-collar street whore and I loved it! I lightly flicked across her engorged clit (about the size of a peanut M&MÓ) several times and I parted her sticky lips with my thumbs and forefingers while orally massaging her inner desires. She began to gyrate against my face and within 3 or 4 strokes she went into a frenzied rage bellowing out how she was cumming so hard her nipples were hurting from the built up pressure.
I am not the greatest of lovers, but I have never had any complaints, either, but this was the first time I’ve ever had a woman tell me she was cumming so hard her nipples hurt! Once she told me that, I really lapped at her snatch. I ran my sopping wet fingers from her pussy down into the crack of her ass and Olivia groaned aloud for me to shove it in her tight ass. She told me, “I’ve never had a finger or anything there before but I want you to finger-fuck my ass so bad, baby.”
Olivia was definitely an experienced lover in some areas, and had no inhibitions at all. She spun underneath me into a sixty-nine position and started to lick my ball sack with intent. I could tell she was close to another climax so I bit down and sucked her nipple-sized clit into my mouth. She screamed and I could feel her hot breath on my balls. Her hands expertly began pumping my hard eight inch cock, as if she wanted me to shoot all over her face, and I had to stop her before I did. I raised up and began kissing her thighs and belly once again allowing us both to regain our composure briefly. I looked underneath myself at her and she was an incredible sight to see. Her hair was all strewn about, her makeup was everywhere except where it was supposed to be, and those lips, ah those plump lips were hardly covered in lipstick as it was all over her face and my crotch.
I had Olivia lay on her side as I got behind her in a spoon fitting position. I rubbed her neck and shoulders with one hand while she guided my hard cock in between her thighs, into her honey-spot. “Ahhhh!” I cried out. I slid in as easy as one would expect, especially considering how wet this lady was, but I was not expecting it to be so tight! It felt fucking great! Instantly Olivia said, “Oh yeah, baby that’s it shove that big cock in my pussy. Fuck me good and hard James, yeah that’s it! Oh God I’m going to, to, to, cummmmmm!”
“I am, too sexy, I am toooooooooooooooooooooo!” is all I could muster as I dumped what seemed like a half-gallon of spunk inside Olivia’s incredible hole of love. She kept rocking against me asking me to give her more and surprisingly (to me); I maintained a majority of my hard on for this Sex Temptress.
I quickened my pace a little just enough to keep the blood flow going in my cock, and that’s when Olivia raised up one of her big legs and began rubbing her nub fast and hard. She rubbed herself into a third orgasm and as she spasmed on my cock; I reached behind her and slipped a finger back into her tight little asshole. In one motion I was knuckle deep in her ass while I was ball deep in her pussy. We were drenched in sweat and I told her I would love it if she climbed on top of me and ride me like a horse. When she mounted me she felt so good, heavy and natural. The feeling of a woman of her weight on top of me made me feel so comfortable and so turned on. She reached behind herself and spread apart her massive ass cheeks to allow for more penetration as I kept driving in deeper and deeper.
After about 15 minutes of this we both knew what was next. Olivia rolled off me and turned on her hands and knees, exposing both of those magnificent holes for me. I got down and licked between the two entries and tickled her click with a finger while tickling her asshole with another. “James, do you want to fuck my big, fat ass?” Olivia asked. “Oh yes I do”, I told her. “Well first, you can pound my tight cunt again from behind, and then when I tell you, I want you to bury that meat in my big ass!” Olivia demanded. I got up from slurping her two holes, and slid my cock along her wet canal making sure to get it good and greased up then I slid in. The heat this lady’s pussy possessed was indescribable. It fit me like a glove, a tight glove.
She looked over her shoulder at me and said, “Come on damnit, fuck me like you want to. Fuck me hard and fast!” I shoved my cock so far inside her tight pussy I thought I was going to hit something. I began slamming her with all I had. I took my right hand and drew back, then let it swing as I made a thunderous cracking sound on her firm, full-sized ass! She winced loudly “Holy Jesus how about some warning next time, sugar?” I could only snicker and gave her a matching shot on the other ass cheek. Olivia raised back to me and let me know that she really liked an aggressive man in the bed. I told her, “Just you wait baby, I’m going to fuck you so hard, you will have to call your boss, and take some time off.”
She laughed and told me, “Honey, I am the boss. This is my restaurant. Now shut up and fuck my fat ass, NOW!” I pulled my cock from one hole, and slid nicely into the other. Her ass was so warm and inviting, I thought I would lose it right there. It wasn’t too long before I was ready to let loose what would be my final load of the night. I pulled out of Olivia and howled at the top of my lungs as I coated her red, rotund ass with my last efforts of cum. As I collapsed on the couch next to her she took me in her arms and rested my head against her warm, pillowy flesh, and caressed my head while we shared a cigar together.
As we lay there Olivia confessed to me that she was in fact looking for a man who would find her age, and size sexy but was not having any luck despite the business she was in. She had known Jack for years, and he had told her about me, and so the ball began rolling. “James, I hope you are not disappointed in Jack or myself for this whole setup”, she whispered. “No, no.” I assured her. “On the contrary, I’m glad this whole event came to pass.’ I was looking to get away for a few days from the hustle and bustle of my everyday life, and this was a great opportunity to do just that.’ I am so glad I decided to come for dinner.” Olivia quickly snapped, ” I’m glad you came, and came, and came again!” We lost it in laughter.
Well that took place about four or five months ago. I wonder if I should ever go back to my town and collect my belongings. Olivia has told me that I didn’t need to. She told me that I could stay as long as I wanted, and that she could keep me dressed in a bathrobe, and if I insisted I could wear my boxers.
I’ll keep you posted if anything new and exciting happens.