Sugars Escort Date

It had been a week since I accepted Megan's job as an escort. I still had not heard from her. So I decided to call her and see if she had any work for me, as it turned out she did the woman's name was Anne she was Forty one and needed some company, I got her details and gave her a quick call.

I decided to give her my real name as my nickname I felt would not be right as that was for my close lady friends. The phone at the other end answered and she spoke.

"Hello who is this?" She asked. Her voice was very mature and quite husky.

"Hi is that Anne? my name is Rob I understand you were enquiring about an escort date."

"Yes this is Anne, why yes I did enquire would you by chance be a date for me?"

"Well yes Anne if you are still interested."

"Why yes it would be good to get out, how do we arrange a meeting?" She asked.

"It is up to you Anne I could pick you up at your home I have a car, I will do the driving and the evening is all yours."

"Well that sounds great, but could I call the agency just to confirm things is that OK?"

"Yes Anne that is fine, here is my number and if you feel comfortable just give me a call."

"Yes Rob that will be good." She replied.

A few days later I got the call from Anne and we arranged to meet the following evening. When the evening finally arrived I got myself ready and off I went it wasn't far to drive, and I could not wait to meet her.

I knocked on Anne's door and she answered. She was quite short, and had long red hair. Nothing like Jessica but it looked good. She was wearing a short tight dress, blue at the top and black on the bottom half.

"Well you must be Rob, good to meet you."

"Hello Anne good to meet you too and you look gorgeous if you don't mind me saying."

"Thank you so much I do try." She replied.

We walked into the front room and Anne stood by her window, and seemed somewhat nervous. She smiled as she spoke and seemed quite happy to see me.

"So Anne are you ready to go?"

"Why yes I have picked a nice place to go and eat if that is okay with you."

"Of course Anne, the night is yours."

We left and arrived at the restaurant some twenty minutes later, we went in and sat down. We ordered drinks and meals at the same time. By now Anne seemed a bit more relaxed and looking at her I would say with no hesitation that this was going to be my second mature adventure.

She did look her age, not being horrible but she looks like she has had a pretty hard time. Don't misunderstand me she is good looking.

We chatted and then tucked into our steak meals, the food was good and the drink was going down Anne's throat like water, I was beginning to wonder if this was a good idea, don't get me wrong she wasn't pissed but another bottle and would be.

As we chatted I looked at her tits, they were good looking big and well very nice. Her figure all over was good, it seems she looks after herself. We finished eating and sat and talked mainly Anne and she told me she had been through a bad marriage.

"He was a right bastard to me Rob." She said.

"He just never had any time for me, he never complimented me, oh he was a bastard."

"Well Anne sounds you are better off without him, I mean you are a good looking woman you have made me laugh tonight and I would say it's his loss."

"Why thanks Rob that is sweet of you to say, I never get out much and I just lost confidence in myself that's why I called your agency I need to know if I still have it, you know what I mean."

"Well Anne it was a good idea that you decided to call, it is a good way to build your confidence back up and as I say you are a lovely lady."

"Yes so you keep saying, but I got to ask you do you think I am lovely enough to fuck?" She asked.

I nearly spat my wine everywhere, I sure was not expecting that to come out of her mouth.

"You see he never hardly ever went near me even if he did he would just get on top do what he had to do there was no adventure there at all." Anne explained.

"Well Anne like I said it is his loss and I mean that in all ways. And well yes you are lovely enough to have sex with." I thought I would be a bit polite in my answer.

"Yes Rob but you have not answered my question. Would you fuck me." She whispered leaning forwards towards me.

"Well Anne yes I would, but you know I could only do that if you requested it." I replied probably sounding like a hooker.

"Well of course Rob I know that, I just wanted to know if you would."

This woman seriously was talking through her drink now and I needed to politely get out of the restaurant before she announced her intentions out loud, she had been quiet so far but that would not last. So we settled the bill and left.

"So Rob is that it for the night?" She asked as we walked to the car. I knew she wanted sex and I felt awkward having to charge her for it. I decided to see how it would pan out.

"Well what would you like to do now Anne?" I asked as we sat in the car putting our seat belts on.

"Well Rob there is one thing I would love to do, it is something I have always wanted to do but he would not let me."

"And what is that Anne? I replied as we drove off.

"Well Rob I have always wanted to suck a cock." She replied.

The car swerved slightly, again she caught me out I mean I am no prude but this woman is more blatant and to the point than Jessica and the others.

"Oh right Anne, you mean you have never done that? How could your ex not have wanted you to do oral on him?"

"Well Rob I gave up on him in the end I mean he didn't have much any way, well certainly not enough to fill my mouth."

"Pissed, this woman has got to be pissed." I said to myself. Surely she is not like this normally.

"Well Anne that is quite to the point, so are you saying you got a big mouth then?" Shit I had no idea why I said that.

Luckily she did not seem to have noticed that comment thank fuck!

We arrived back at her place and she invited me in for coffee.

"Sit yourself down Rob and I will make a cuppa." She said.

I could see her walking around in the kitchen, she was slamming the cupboard doors shut, the spoon sounded like a sledge hammer as she banged the sides of the cups. She came in and gave me my cup and sat, not next to me but in the arm chair, which I thought was quite strange.

"So what do you think of my house? not bad considering it is all I got out of the bastard." She said.

"Well Anne yes it is a good sized place. But can I ask, you sound so angry about things how long has he been gone?"

"Two years something like that. But I am sorry Rob what must you think of me? I think it is because I have drank too much, red wine makes me very truthful." She explained.

"No worries Anne it must be hard." I replied.

"What's hard Rob?" She joked.

"Anne you are funny." I replied it is all I could say.

"So then Rob, let's talk business. I want to Suck you off, so how much would you charge me?"

Shit I did not know what to say I did not want to sound so business like, boy am I new to this game.

"Tell you what Anne you know the price for a over night stay so why don't we agree to that price?"

"Oh OK so I can have you till the morning? that sounds fine."

She then got her purse out and called our payment line and paid her fee, I did try to stop her but it was a waste of time.

"So Rob that's done and out of the way so how about you come with me to the bedroom it is more comfortable."

Into the bedroom we went, and Anne encouraged me to relax on the bed, I kicked off my shoes propped the pillows up and laid back to wait for what was to come. Anne then laid next to me, now this close she was beginning to arouse me.

"So Rob here we are, I must say you have been making me feel horny all night. I really want to touch you can I?"

"Go right ahead Anne, like I said I am all yours."

She began to un zip me and fumbled about and pulled out my cock, she then began playtime.

"Oh my Rob I am impressed, do you like my touch?"

"Yes Anne err oh yes your touch is just fine."

"Hmm good I have not felt a cock like this, can I suck it? I mean you know I want to I told you."

I did not refuse I was just about hard now and looking down her cleavage I wanted her mouth badly. She moved down the bed slightly and with a bit of caution started pecking at my head, her lips felt good as she went a bit further down, and continued wanking me.

"Mmm mmm mmm...oh my am I doing OK? I mean this is so new to me mmm mmm...I am only living out my fantasy."

"Anne you are doing fine you stay there as long as you like."

She then moved herself down and ended up between my legs. She then continued, taking my full length, I watched her head going up and down and I wondered if this was truly the first cock suck she had ever done.

"Wow Rob this is so good, I never imagined it would be like this and you are so hard. And my other fantasy thing I would love to do is to get fucked on top."

Shit I am now thinking she wants to ride me, but she had no intention of doing that just yet as she pulled her tits out of the top of her dress and began to rub one of her nipples against my cock.

"I am loving your cock Rob, hmm it feels so good against my tits. You didn't answer my request just now, I want to go on top I want to feel what it is like."

"Anne whenever you are ready just climb aboard."

With that she went up on her knees and positioned herself over my up right cock, I was looking forward to this. She lowered herself my cock just touching her pussy.

"Oh it is a bit tricky shall I just push ooh down?"

"Fuck yes Anne lower yourself oh fuck that's the way." I felt myself go into her she was wet and loose.

"Awww fuck! Oh fuck Rob!" She shouted as I went into her.

She began to find her rythm and I just laid there and watched her slowly riding up and down.

"Awww fuck Rob this is so good oh my awww awww yes oh."

I slowly began to pump her as she pushed her dress down to her waist and took her tits and began to rub.

"Hmm oh my that feels good fuck me harder oh yes Rob oh my no not to fast oh yes that's good."

I slowed back down for her as I was getting carried away. I so wanted to fuck her from behind but she just seemed to be quite happy on top after all it is her fantasy.

"Oh Rob I am going to orgasm fuck yes make me feel it oh yes oh yes Rob oh fuck yes yes thrust me oh that's it oh yes oh you are fucking hard in me oh yes don't come though Rob oh fuck yes, yes, awww awww awww yes."

She came hard, and I continued to thrust her wet pussy. She fell back slightly and began to slide backwards and forwards on me fuck it felt good. She finally came off me and laid next to me.

"Can I make you come in my mouth now? I want it."

"Yes Anne suck away lady." I replied.

She went down on me and began to fuck me, her mouth sucking me hard as she wanted me to shoot in her.

"Fuck Anne yes keep doing it I am cumin get ready fucking hell." I yelled.

"Mmmm...mmmm...mmmm..yes mmm mmm ahh!"

I shot into her mouth fuck it was good, she was good.

"Well Rob did I do well? Did I please you?" She asked.

"Oh yes Anne you were awesome."

I was a bit disappointed it did not last too long but it was her night and lets face it she was probably a bit wary of things. I stayed a bit longer and as the birds began to sing I gave her a kiss and left for home and a bit more sleep.

The following morning I got up early, while in the Shower I was thinking about Anne. It actually went well being as it was my first time escorting, I think I pleased her.

While thinking about her and the evening I started to get hard, I was semi already you know how it is. I jumped out of the shower and rushed to get my oral sex toy, yes I have a toy, I mean why not?

I got back in the shower and stuck it to the wall. There it was pouting lips enticing me to fuck it. The shower gel lubed it up and I began to tease it with my cock, running the head around the silicone lips the hot water heating it up.

I began to slide in nice and slow they are quite tight. Once in I began to slowly thrust hands on the wall. I imagined Anne's mouth taking me Her moans of delight. Oh fuck I quickened as I fucked my imaginary Woman.

Harder I could hear her husky voice demanding, I pumped hard into her, the ribs of the inside hitting my nerves I felt myself beginning to cum. Harder she mumbled, I came out and entered again.

That was it I fucked her mouth harder and came intense hot and fucking good stuff I said to myself. I finished washing myself got dressed and had breakfast, while eating I knew I wanted her again.

So I called up Megan and got some info on Anne, I told her Anne had left something behind and I needed to find where she worked. Megan gave me Anne's Company name, a bit of research and I had the address and phone number.

I gave her a call just to make sure I had the right woman, I pretended I was checking to see if she was OK, and enjoyed her evening. This she confirmed. We chatted for a bit and said our goodbyes. That was it I was going to pay her a visit at work.

I arrived at a small office block in a industrial park. I got out of the car and walked into the entrance, the place seemed to be empty. Anne's office was top floor so up the stairs I went, a bit of a walk round I finally found her office door.

Should I knock? should I just walk in? I decided to knock but there was no answer. So putting my hand on the door handle I slowly opened the door and stuck my head into the void.

I could hear Anne talking, I assumed she was on the Phone as I could not hear another voice. I followed her tone and arrived at her office door. I knocked gently and was requested to go in.

There she was on the Phone, and I must say she looked even better than last night. She had a orange sleeveless blouse, buttons open showing her cleavage. She looked over with a look of total shock. She ended her call rather rapidly.

"Oh my Rob, wow what are you doing here?" She asked.

"Well Anne I was actually just passing so I thought I would pop in and say hello." I replied.

"Oh but you said hi on the phone this morning."

"Well yes Anne but you know, I could not drive past and not pop in, could I."

"Well I guess not, I am a bit busy though I have a report to do for my accountant." She replied.

"Oh OK Anne. So what do you do here?" I asked.

"Shame you never asked me all this last night, well I sell women's clothing and accessories."

"I see, is business good?" I asked.

"Why yes thank you. Now Rob why are you really here?" She asked resting back in her chair.

"Well Anne I am going to be straight with you. I enjoyed our time together last night and well I want to see you some more." I replied.

"Oh I see, well I will book you again at some point when I need you." She said in a quite shitty tone.

"No Anne I am not here on a business visit. I am here because I want you again, you understand?"

"Yes Rob I understand, but why? Why do you want me?"

"Well you are a glamorous woman, you hit my spots last night in all ways, you look good, smell good and I want more of you."

"So your not just wanting to use me because you feel horny? You really think that of me?"

"Yes it is all true, Anne I want more than we had last night, I mean we could have done so much more with the night."

"Like what Rob? You know I have not had much experience what do you want?" She asked.

She got up and went to her filing cabinet, she was wearing a short tight skirt with fish net stockings and stiletto heels. I looked at her arse and wanted to fuck it badly. She sat back down behind the desk and pushed herself back in the chair, looking at me.

"Rob you have not answered me, like what?"

"Well Anne if I said even sitting here with you I want to fuck you from behind what would you say? Would you want it? have you ever done it?"

She just looked at me and gave a slight smile, that was enough for me to know she wanted sex. I could tell I have seen the look before. She then began to slowly stroke one of her tits.

"I am sorry Rob I may have sounded a bit of a stroppy cow with you, but that is me. I want you now, I want to go down on you here and now. I want your cock in my mouth, I could not sleep last night thinking about you."

She then began to undo her blouse, not fully just enough to fully reveal a black front fastening bra, her tits bulging out of it. She got up and walked around the desk, and rested against it putting her heeled foot onto the edge of the chair I was sitting on.

"So then Rob here I am, what are you going to do now? I really have not much time."

I stood up walked the very short way to her and kissed her hotly on the lips. She clung onto the desk with her hands, her shoulders back and her tits sticking out. I kissed her neck and took her left nipple.

"Mmmmm Rob that feels good mmmm." Anne sighed.

I felt her fumbling with my belt and slowly lowered the zip on my jeans, her hand sliding into them and finding my semi aroused cock. I kissed her again teasing her tongue into my mouth, She lifted her arms over her head as we kissed. I wanted her badly and she knew it.

"Oh let me suck you Rob I want your cock."

She lowered herself down, and slowly wanked my cock now fully erect. Then her lips touched and slowly pushed her mouth onto me.

"Mmmm mmmm mmmm awww mmmmm so mmmm nice mmmmm."

I took off my shirt and kicked off my jeans and shoes as Anne sucked away, her hands holding onto my thighs. Fuck she felt so good.

"Oh you are pleased to see me aren't you? Mmmmm I can't mmmmm wait for you mmmmm to fuck me mmmm so good mmmm mmmm mmmm." She mumbled.

"Fuck Anne oh fucking hell I want to fuck you, let me fuck you now." My response to her suck.

With that she stood up and went over to the desk slightly bet forwards her head looking back at me over her shoulder. She then lowered her blouse off her shoulder. I walked up to her ad pushed up her skirt.

"Come on Rob I want to feel what it is like awww come on."

I stroked her arse and toyed it with my cock, lowered it and stroked her pussy with it. She pushed her arse onto it begging me to take her. I could not wait and pushed myself into her pussy. She was wet and felt tight.

"Oooo my Rob mmmm that feels so good mmmm slower Rob I want to really feel it going in and out awww fuck."

I fucked her slowly my hand moving up to her right tit. I stroked the side of it as I pumped into her. She removed her blouse fully and threw it on the floor. With that I grabbed the chair and lifted her leg onto it, her heeled stockinged leg resting sexily.

I began to quicken as she looked back at me sexy groans pouring out of her mouth. I pulled out of her and went down on her wetting her arse I wanted it. Up I went again and teased her arse and slowly pushed into her. She grabbed the opposite side of the desk.

"Awww Rob awww fucking fuck Rob oh oh yes yes."

Her arse felt great as I began to fuck it good and hard. Anne screamed out in pleasure it was turning her on even more as she pushed herself right down onto me. I pulled out and took her pussy again, I fucked her this way for a bit longer and pulled out. She turned around and leant on the edge of the desk.

I lifted her right leg and began to kiss it from the ankle working my way down to her knee, then teased her inner thigh, hooking her leg over my shoulder I came to her pussy, my mouth took her straight away. She tasted good, and I felt her hand rest on my head encouraging me.

I stood back up and entered her hooking her legs up by the knees. I leant forwards and we began to kiss. she wrapped her arm around my neck. Resting her legs on my shoulders and my hands on either side of her on the desk I pumped my cock faster into her still kissing.

"Oh Rob I am cumin oh yes oh yes oh yes keep fucking me like this oh fuck yes Rob oh yes."