All people having sexual activity in this story are eighteen and over.
The videos were incredible, everything was consensual as all the ladies in the videos were loving what they were doing. I wondered where the cameras were; I checked the bedroom, there were three HD cameras hidden in the smoke detectors, the same in the lounge, there were also some naughty videos from the lounge. Liz and her sister were always in a threesome, though there were lots of videos with Liz solo, she was hot. I wondered if she'd send me the lingerie pictures.
I went back into the safe as there were a couple of drawers; I hadn't opened I wondered what weight of gold was in there. The first drawer had several keys with bank names and branch addresses on them I took them as Safety Deposit boxes there was also a Rolex box with a note on it which read 'Jill's 21st' I opened the box disturbing nothing inside was a solid gold ladies Rolex with a gold bracelet I thought Tom must have appreciated her I thought of one video when Jill told her mum to eat her pussy so her tight pussy would be ready for Tom's hard cock.
It was now close to nine I'd better get home as I felt a little tired, I came out of the Penthouse I didn't use the elevator I walked down the stairs the elevator door opened out came Bill, my accountant's mother, she had been widowed a couple of years ago. She was in her mid-sixties. She was still a looker; she also ran The Ladies Luncheon Club, which involved over a thousand ladies having lunch every month in the hotel, "Good evening Mrs Grey, how are you?"
"Barry, please call me Judy, I'm so sorry about Tom, he was a gentleman, I believe you'll be running the hotel, which is good as you have been around the hotel for a long time. There are over eleven hundred ladies tomorrow. We have an excellent author speaking your mum and Dr May I've arranged they sit at the same table as the author he's promoting his new book. I'm sure Babs will get an autographed copy for her collection; how many books does Babs have?"
I smiled, "Judy, I do not know all her life she's been an avid reader it seems to relax her when she reads, she'll enjoy tomorrow I'll be on duty I'll make sure she's sitting next to the author."
"Barry, could you be a darling and have me sitting close to him I believe he's a handsome man knowing my luck he'll probably be gay, I'm going in for a nightcap would you like to make my day and join me for a glass of wine?"
"Judy, I'd love to do that but only one glass as I need to get home to mum, I should have been home now so I'll message her to say I'll be there in half an hour."
I followed Judy into her apartment. She led me into the lounge, "Barry, message Babs, I'll get the wine I need to change my bra, it's a new one I got this morning, one of these push up ones. I got it for tomorrow's lunch. I won't be wearing it as it's cutting into my left tit. It's such a hard job to get a bra, I'm comfortable in for my big girls."
I messaged mum telling her I'd be home in thirty minutes. I also told her she'd be sitting next to the author at tomorrow's lunch.
Judy came into the lounge with a tray with a bottle of Chablis in a cooler and two glasses. She wasn't wearing a bra; her massive juicy tits were jiggling beautifully. She had huge nipples that were hard. I poured the wine. Judy sat on the couch beside me. We clinked glasses. The Chablis was delicious, "Judy, that's a gorgeous Chablis. It's far better than the Chablis we are selling, where did you get it?"
Judy smiled, "Bill, my husband, we had a motor home which we travelled to France in twice a year. We'd fill it up with wine, unbelievably the Customs did not stop us. We did this for years after Bill died. I did it myself for a couple of years sadly the uncontrolled Muslim immigration is a problem. The last thing I wanted was having six Muslim guys with their cocks out wanting their wicked way with me, so I'm not sure if I'll go back."
"Judy, this wine is gorgeous. I think I need to change the wine list in the hotel, as the quality is not that good."
"My Bill and I have been telling that to Tom for years, but I felt he'd have some kind of loyalty to the wine merchants he was using. Bill even explained the price difference: these wines are over forty percent cheaper than the price you're paying and the volume of wine you sell, you'd probably get it cheaper. I'm fluent in French after the lunch tomorrow, come over here in your car, I'll give you over thirty different wines and Champagne that are far better than anything you are selling. I feel much better without that bra on, do you like my big girls?"
As Judy said this, she bounced her massive tits in front of me they looked incredible, "Judy, I love your wines I would like to work with you with them I'd love to chat tomorrow afternoon I also love your big juicy milkers they look fantastic."
Judy smiled, "Barry, I'd love to do that with you, my suggestion would be buy a container load of wine as you could have it here within a week. I don't know what storage you have at the hotel, but you'll need storage. Maybe we'll need to fly over to France, that would be fun. I'm pleased you like my big girls; you can feel them if you like. One thing I must say is I have needs and urges which I'd like you to look after. We must be discreet about this, as I don't want young Bill to know. There's also our age difference, which is not a problem for me, I'm a woman who knows how to give a man pleasure. Give me a cuddle, have a good feel of my milkers as that arouses me so much."
We both put our glasses on the coffee table I took her in my arms she brought her mouth to mine we tongue kissed spontaneously our tongues dancing in each other's mouths I felt Judy's massive tits she grunted with pleasure, "Darling, that feels so good unbutton my blouse take them out suck on them, how late can you be for Babs? I'd love for you to bring me off. I'll phone Babs when you leave to tell her we'd been discussing wine, as she knows I only have excellent wine. We'd spoken privately about this. Babs was not keen on the hotel's wines too, that feels so good make me cum tonight I'll look after you tomorrow you'll be the first guy I've had since my Bill died let me pull my skirt up, I took my thong off when I took my bra off as I'm so wet."
I had Judy's blouse off in seconds, her massive tits sagged, but they were still big and beautiful, she'd pulled her skirt up. It was now above her hips. My big surprise was her vulva was swollen and hairless. I'd always the feeling that older women would have hairy pussies as I ran my finger up and down her long sex slit. I'd been nibbling around the meat of her massive melons. I came off her breast, "Judy, I love a smooth pussy, my tongue works so much better on smooth, would you like me to bring you off orally?"
"Everything you're doing feels so good after my Bill died, a girlfriend told me, we'd too much to drink one night we ended up in bed. She went down on me, she shaved my pussy, it made me so much more sensitive down there, so I've kept it smooth ever since you'll be the first man to go down on me, I'm happy you like my old body."
I couldn't believe it Judy's body had given me a monster erection as I spoke, I took her hand as I placed it on my monster cock, I said, "Judy, your body arouses me so much feel the erection you give me just with looking at you take him out and play with him while I bring you off."
Judy's fingers were so nimble as she freed my monster cock, Judy's eyes were focused on my ten-inch-thick monster cock, "It's beautiful, it's so long and thick. Barry, bring me off then take me as I want to feel this beauty inside me as my pussy is getting wet just looking at him."
Judy caressed my cock and balls; she had a gentle but firm touch. I was sucking her left nipple as my fingers spread around her gorgeous vulva; I parted her thick cunt lips as an enormous hooded clit popped out when I saw the size of it; I knew when I sucked it, she'd cum quickly.
Judy was now giving me an excellent hand job as my head moved down to her hot pussy, as I fingered her pussy, I was thinking how beautiful it looked. Judy was in her sixties; she would be the oldest woman I'd ever fucked. I spread her thick flaps open. She gasped when I teased her clit with my tongue, "Judy, you have a treasure of a cunt, everything about is perfect. Please relax, enjoy what I'm going to do to you."
"Barry, no one has ever called my pussy a treasure before, will I call it my treasure hole? I love what you're doing to me. My pussy has been neglected for so long, my god nobody has ever nibbled the insides of my pussy lips before, give me another finger darling I can take it."
I was now sucking her clit finger fucking her with three fingers, my head was bobbing on her huge clit. Judy was riding my mouth, pushing her pussy against my mouth as she rotated her hips as though she were riding my mouth. I felt the warmth of her cum in my mouth as she cried out, "I'm cumming, this is so good, let me be your slut Barry, I'll do anything you want."
Judy's whole body twitched as she climaxed, there was so much cum I'd to swallow some but I held a lot in my mouth. When she'd composed herself, I took her in my arms she was looking at me with a look of satisfaction on her face I stuck my tongue out to show her the blob of her cum I'd saved for her, we cum kissed lovingly for several minutes until there was none of her cum left in my mouth.
I lay Judy on top of her sofa; she spread her thighs wide for me; she was so wet I slid inside her easily. Judy gasped when I gave her my full length until the head of my cock was hitting her cervix. I soon had a powerful rhythm going as she wrapped her legs around my hips on every third thrust, I'd go deep, she loved it, she would grip, release, grip release she was giving me a great ride, "You're the best, I love your gorgeous cock, you have a treasure of a cock, I feel stretched it feels so comfortable, the length is giving me incredible sensations. The thickness is also fantastic. Fuck me harder darling, I love it when you go deep."
I began vigorously pounding her pussy; I was riding her, she was riding me, "Barry, I'm so close let's cum together let me feel your creamy spunk spurt on my cervix I'm loving everything you're doing to me, you're giving me a great ride I'll help you with the wine but I want you again. Cum for me, I'm cumming."
I came within seconds of Judy; her strong cunt muscles had brought me off. We kissed and fondled for a couple of minutes afterwards. I went to the bathroom to use Judy's bidet, as I was smelling of sex. I came out and Judy thanked me. She told me she'd put some wine in her car so we could taste and compare tomorrow afternoon. She told me she'd be at the hotel at eleven, as she needed to collect the money from the ladies.
The first thing I did when I got into the car was check my phone. Liz had replied with the message 'Hope you like', she'd attached twelve pictures of her in seductive lingerie. She looked gorgeous. I was taken by a crotch less Teddy, she was wearing a G-string with it, I replied, "Liz, you look gorgeous you should have gone crotch less with that fabulous Teddy the G-string wastes it, are you swimming tomorrow?