I will admit I did notice him before he approached me. In fact, I thought he was approaching me because I had been casually eye flirting with him.
I was trying on full length coats when he approached and said “Are you Dear Diary” I was a little surprised, and I believe he could tell by the look on my face. He apologized and said I hope this isn’t inappropriate or overstepping any type of boundary.
I said no, not at all. I am in fact, my name is Holly. He formally introduced himself and quickly changed the subject from the lifestyle which I appreciated. He commented and offered his accompaniment if I so desired in his own words.
I told him I was out for the day doing some Christmas shopping and would love to take his arm for the day. So I disrobed from the coat, put my arm through his and we started walking.
I couldn’t help but noticing he smelled absolutely wonderful. When we stopped walking, I leaned in, got on my tippy toes and smelled his neck, I held my breath in and let out a nice warm breath across his neck telling him he smells very sexy.
He replied with a thank you, turned in towards me and asked me if I could spend the night with him, I was taken by surprised, but did not say no. I told him there are some factors involved with the answer to that question.
I tug down on his lapel, whispering in his ear, asking him if he’s circumcised and hung. I also whispered in here telling him I have a piercing a deep throat and like anal probably a little too much.
He replied with all of the right answers. I asked him if he had any fetishes that could be viewed as violent. He told me he has no strange fetishes, and he admits to be somewhat of an old-fashioned, romantic fool.
He had offered to take me shopping for the rest of the day to set the mood for the evening. After sitting on a bench for a little bit talking back-and-forth, we walked back to the store where we had first met.
He had mentioned he wanted to gift me the coat that I had been wearing when he first approached me. I refused and he insisted.
We spent the rest of the afternoon shopping when he had asked about dining. I replied I don’t eat a lot and what I do is mostly vegetables, although I wouldn’t mind a nice cocktail or two.
Unfortunately, we couldn’t leave my car due to the high theft risk. I asked him if he wouldn’t mind taking and dropping my car off at my house.
I pulled the car into the garage and asked if he wouldn’t mind coming in for a quick cocktail to get a Head-start Wink wink. We held hands to the front door, brought him into the foyer, and before he could take his coat off, I fell to my knees unbuckling his belt, undoing the button to his pants and pulling his zipper down.
You could tell I caught him by surprise because he was completely soft. I grasped his balls a little firm, popping them together while sucking his soft cock into my mouth.
We kept saying “oh fuck oh fuck” over and over.
I thanked him for treating me like a Queen all day today, and I was going to show him how a queen treats a king. I stayed down on my knees until he released his load. I milked him dry, cleaned him up and asked him to come watch me change into something for tonight.
He was in slacks, a long sleeve button shirt that was tucked in and some extremely nice shoes. He had a lot of jewelry on a very nice watch and a couple of beautiful gold rings. He stood about 6 ‘4” so I was thinking I could wear some heels.
I invited him into the closet and asked him to have a seat while I get dressed. I kept asking him to pick something out, but he was reluctant..
I pulled out a cute little sheer black dress pull it over me and ask him if this would be too much. I asked if he would be embarrassed to be seen with me in this dress as it was completely see-through. He replied no it is wonderful.
I threw on some nipple bands to keep my nipples, nice and hard, platform stripper heels and a black beaded choker, topped it off with some Ruby red lipstick to match the ribbon on the back of the heels and the choker.
We jumped into his little car and started our trip downtown for some cocktails. I could instantly tell his attitude went from being a complete gentleman to a super confident sexy man. I asked him if he would like to role-play for the rest of the evening. He admitted to never really thinking about anything like that.
I could pretend to be his niece on his ex-wife side, I could be a mistress while his wife was out of town, I could be a coworker or I could just be a special girlfriend for the evening.
He replied I think you’ll be a lady I met at the mall. He humbly told me that he’s never done anything like this or met anyone like me. I told him that was a nice compliment I was honored to be on his arm for the evening.
We went into the restaurant, had quite a few cocktails and decided to go back to his place finally. In all honesty I have been yearning to have him inside of me all day. The first time I saw him I was imagining him fucking me with my ankles around his shoulders and neck.
We went back to his place. It was extremely neat and tidy, which was not a big surprise. He asked me if there was anything he could get me. I replied I just need you to fuck me.
He led me back into his bedroom, set me on the bed and asked me if I could leave my shoes and choker on. I told him he was reading my mind. I turned my back to him, asking him to unzip my dress. It fell to the floor. I stepped out of it,
I bent my knees and squatted all the way down my knees were apart. I pulled one of his feet forward to take his shoes and socks off one at a time. Before I stood up, I took one of his feet and rubbed it on my pussy.
I stood up, unbuttoned his shirt, took it off and started biting his nipples. I looked up at him and told him tonight’s the night you’re going to do anything you want sexually.
I unbuttoned his pants they slid to the floor. He picked me up, plopped me on the bed and instantly went down on me. She would lick my pussy for a couple of minutes, then come up and rub his pre-cum all over me.
He would go back down, clean himself off of me, licking my pussy while tongue fucking me. His oral skills were completely amazing. His tongue seemed to be very stiff and very hard unlike most.
I occasionally tried pulling him up to take his cock in my throat, but he insisted on giving me oral. I told him I wanted to kiss him. I told him I wanted to taste my pussy on his tongue.
He fell for the trap. I brought him up, started kissing him, turning him on his back. I finally have my chance to have him in my throat. I’m not bragging, but I’ve never had a man tell me that I’m not the best when it comes to throat fucking. I fucked his cock with my throat as long as I could without a break.
I came up rubbing my throat and smiling when he offered me a glass of water that I could not refuse.
We both gulped down some water, he turned and asked me who made you like this. How does one become so sexually comfortable, knowing and aggressive. I replied we’re just getting started.
I asked him how he wants to fuck me. I asked him if I was going to be able to produce more cum with another ejaculation. He told me that the second and third time would be less volume, but he would be able.
I told him the reason I was asking is because I have a cum fetish. I told him I adore being sprayed and slathered with cum. I told him that he could fuck me anyway he wanted as long as I get his cum on my tits.
He told me that I should have pumped his cum on me earlier this evening instead of swallowing it.
So we jumped back up on the bed when I started rubbing my pussy I was looking into his eyes, asking him to fuck me. I asked him if he wanted to fuck hard and rough or look me in the eyes and fuck me slow.
He grabbed my ankles, putting them together, holding them in the air as I was on my back. He asked me to lock my knees and squeeze my thighs together. Once again he plunged his face down into my pussy, squeezed between my thighs.. he licked me until I was dripping wet. He came up and plunged his cock into me slowly.
He was pushing my thighs together while slowly fucking me. I had asked him not to go so deep right away. He asked me if I liked this position. I told him that it’s a little tight so please don’t go real deep.
I was pinching my nipples and starting to moan pretty good when I asked him to go a little deeper. He was really getting into it vocally when he started asking me if I like big cock
I would moan and say yes I love big cock. I love cock. Please put your cock in me. Please fuck me with your cock. I would just moan and beg to be fucked over and over. I would just keep saying fuck me hard fuck me fuck me.
About 20 minutes into it he was starting to go real deep and real fast. He was fucking me real good, real hard and real deep. Another one of my fetishes is anal I love cock in my ass.
It seems like the more my pussy gets fucked the more I want it up my ass. The only thing better than getting my ass fucked is getting my pussy, my ass and my throat fucked all at the same time.
after about a half an hour of him pounding me, I told him I want my ass fucked. I asked him to fuck me in the ass. He told me he has never fucked anyone in the ass before. I told him he’s going to love it.
I asked him to rub oil all over his cock. I asked him to smear oil all over my ass. I told him he needs to get up on his feet straddle over top of me as I get faced down ass up and just dip his cock into my ass. I told him you’ll need to put the head in first and just hold it there for a couple of seconds. I told him don’t go in hardly at all until you move it a couple of times..
So here we were I was faced down ass up. He had his head in moving it in and out about two minutes later, he was able to force it all the way in to his balls. It wasn’t long at all before he told me he was about to cum.
He flipped me over, shot his load on my tits. I rubbed it all over, pinched my nipples, grabbed my knees up to my ears and told him to put it back in my ass and fuck me as long as he needed to. He wound up, pounding me pretty good and eventually wound up pumping come into my ass..
We showered off he made us something to eat, and he took me home. He told me he wasn’t able to see me as much as he would like, but he would definitely get a hold of me when he can. We see each other about three times a year when he has the means
Just when I think he found a girlfriend or a wife, he’ll call me up for another arrangement.
He’s a great guy, a gentleman and a wonderful fuck. You know who you are.
Dear_diary Holly