"Fantastic Fantasy" for one woman to play along...

mastaofhisown

Experienced
Joined
Mar 31, 2005
Posts
34
I am going to give an idea of what I am looking for before the story starts. As a teenager I grew up wanting to be with older women. At 16 I wanted to be with a woman who was like 26-38. I always wanted to meet her and then go out with her. I am going to strart of the story as a 21 year old. (my acctual age) ONLY one woman is needed for this story...

Usually I just stopped at a fast food restaurant to grab some food for break when I am at work. I had a few extra minutes to kill before I had to be to work so I decided to go to the grocery store. As I came through the doors I tried to think of what it was that I wanted to get. Should I get a sandwich from the deli? How about something I could reheat like some chicken and potatos? I was so undecided I began to walk around and just go up and down each aile of the store hoping that something would pop up taht would be what I want.

As I came around the corner to the next aile. I found myself looking at a very beautiful woman. She looked like she was in her late twentys or early to mid thirtys. I am not to sure i just know that she looked very beautiful. As I walked down the aile towards her i thought to myself now that is something i want. I could feel myself getting excited as i got closer to her. She was wearing a skirt that was slightly higher than her knees. She had a pair of stalkings on and a pair of high heel shoes that were black like her stalkings. She has a jacket covering a white shirt that was not low cut but came down on her chest. It was closed by buttons and if she were to unbutton just one then she would have clevage. She looked like she had an upper c cup size breast. Oh how I would love to see them. Her hair was up and pulled to her head by a little hair clip. Through the out line of the skirt i could see the shape of her ass, it was very nice and round but not large at all proportionate to her height. I always had a thing for women who were slightly taller than me. I am 5 8 she looked like she was about 5 10. As I got closer I had such a disire to talk to her. I didnt know what to say or if I should, so I kept on walking.

I went about thinking of her as I tried to find something to eat. All I could do was think of her. I wanted to talk to her go out with her have sex with her be seen with such a beautiful woman. I turned down the aile for water juice and soda. I needed to grab something to drink for work. As I picked up a half gallon of juice and turned around to head in the other direcetion, the woman came turning into the aile. I got an immediate rush through me and found myself half hard as i was walking towards her. My heart was beating uncontrolably as we neared each other. She looked towards me and flashed me a smile. Her eyes light up as she smiled at me. It felt like an angle looking at me. She had the most beautiful smile i had ever seen. She had full lips not large ones but full even lips. Those were another turn onto me besides the outfit and the shoes and the stalkings. I loved to see women in skirts and stalkings with high heels just something i always found a turn on. I flashed a quick smile back and walked past her. I turned the corner thinking was that an invite to talk to her? was she just being nice? did she want to talk to me as much as me wanting to talk to her? No way i thought to myself clearly she could tell there was an age difference. Maybe she was into that to?

I turned around and went back to where I saw her. She turned as she saw me walking towards her. I could see her eyes widen slightly as i walked towards her. I approached her and came to a stop infront of her.

<Hi My name is Jeff.>
 
Last edited:
It was the day before my thirtieth birthday. I did not really plan to celebrate it, my life had been a bit of a mess lately, and I did not feel like celebrating at all, but I had decided that it was a good idea to have some snacks and some wine at home anyway.

While I was in the grocery store I noticed I was being watched by - I am almost tempted to say by a boy - he looked like 20 or 21 at the most. Very good looking though, the thought flashed my mind right away that if I was just a few years younger I would just go over to where he stood and strike up a conversation...

As I walked through the store looking for something I suddenly saw him again, standing at the other end of the aisle, with a bottle of juice in his hand. Again, he looked at me, and I couldn't help but smile at him. He walked towards me and I almost expected him to say hello, but he went on. Why was I feeling so dissappointed? "You are almost 30 years old!" I told myself. "You are not a girl anymore, and if you want to talk to someone, just go and start doing it!" But another voice in my head kept nagging about that he must think it weirdly if a woman my age was starting to talk to him. Surely, there must be lots of young girls interested in him.

I turned around to look after him, and I could see he had turned around too. When he walked towards me, I felt my heart beating.

Hi my name is Jeff.

I smiled. "Hi! I am Riky."
 
<Its nice to meet you Ricky! I was walking through the store and i couldnt help but noticing you. I debated wether or not to come and talk to you figuring it would be weird for some one my age appraoching an older and my i say very beautiful woman. But i figured waht the hell go and say hi.>
 
She frowns for a second when he right away points out that she is older than him. But in saying that so freely there is a certain naiveness she finds endearing.

"Well, I am glad you did say hi after all... Hm, do you have all you wanted to buy? Maybe we should leave the store and go sit down somewhere instead?"
 
I had to think for a moment. Can I miss an hour or so of work? All thats due for today is done. I guess an hour or two wouldnt hurt.

<There is a few more things i need to get before we leave if you would like to shop around with me for a few. I just have to call work and tell them that i am going to be in later than i was planning. After i do that i shall be free.> As we began to walk around I was wondering if she was upset by me having expressed the age difference. Either way if she wasnt interested she wouldnt have asked me to do something. I just couldnt help but feel completely turned on that i was now walking with a woman that i have fantasized about being with, talking to, or just having a conversation with...
 
The fact that he wanted to skip work for me made me smile - he must really be interested in talking to me! I felt my heart beat go a bit faster, looking at him, his face still so young and almost innocent looking, and his body - still no sign of a beer belly or anything similar, as i seemed to notice so often with the guys my own age. I tried to tell myself to calm down - I was about ten years older than him after all, possibly he just wanted to talk a bit... but I sure hoped he had more than that in mind.

I was glad we got to walk through the supermarket a bit more - this way I could get in control of myself a bit...
 
As we were walking around i found it a little hard to talk to her mainly beacuse of how i felt about being in the presence of a WOMAN, I was scared and turned on at the same time scared because it felt kind of wrong but turned on because this is a fantasy for me. I made as much talk as i could.
<So tell me where do you work? I mean are you a business woman?> As i was waiting for a response i found myself day dreaming of what it would be like to watch her walk by me in work every day. God there must be a lot of guys that are interested in her. I mean look at her, she is beautiful with a nock out body....
 
It was nice walking there with him, chatting to him. I told him a bit about my job, and about other things. Then we had all we needed to buy and approached the check out lane...
 
Having made a great conversationist so far she was quite delightful to be around as good looking as she was her personality was even better. I still couldnt help but feeling so turned onto her. Since she had been grocery shopping as well I was almost sure she wanted to bring her stuff home before we went for coffee. I looked at my watch and thought well since i was buying food for my break at work maybe i could just use this tomarrow night and we could go out for a bite to eat. Curious to see if she would like to i turned to her...< You know the reason i was here shopping was for food for my break i was wondering if you would like to go get dinner instead of just coffee. I am sure you havent eaten yet, plus i know a great little italian place about 20 minutes away. Sound like something you would be interested in doing?>
 
I liked talking to this guy. He was quite good looking, and also fun to talk to. Actually I did not have the feeling of talking to someone younger than me, he could definitely hold a decent conversation.

When he asked about dinner I noticed that I was quite hungry indeed. But also, I liked the idea of talking more with him.

"Yes, of course." I said, smiling. "I love italian food."
 
Well if you love italian food i know one of the greatest italian restaurants in this counrty. The cheif there is an old friend of the family and he came from Italy like 35 years ago and has had this place open for about 20 years. I have my own table there because i know him and becuase i go there every friday night. So it wont be a problem getting a tabel. Though i think you might want to bring something with you that can keep you warm the fire place might not be enough on an evening like this.

As we walked through the parking lot i couldnt help but think i just asked out a gorgous woman and she said yes. Should i think this to be a date? and unofficial date or is it official. I didnt want to ruin any thing so i kept my mouth shut. However i was completely turned on so much more now than i had been before. I was going out with a very hot woman tonight...
 
"That sounds great!" I said. On our way across the parking lot I told him about how not just italian food, but Italy in general had always fascinated me, and how I finally had gone there last summer. "I could show you the pictures some other time." I said.

We approached the cars, his stood not very far from mine...
 
I would really like to see those pictures. I have always wanted to go to italy. So i will follow you to your house so you can get ready and put your grocerys away. You would mind if i was to change into something better than this i have some cloths in my car?

I thought to myself breifly about how turned on i was asking a beautiful woman to change at her house. I hope she didnt mind me asking but part of me wanted her to flirt and say something back to me. I was already completely turned on to her.
 
For a second I hesitated - after all he was a guy I had just met half an hour ago, should I let him to my house? But he seemed so friendly, and innocent, that I just couldn't believe he'd be up to anything bad.

"Yes of course, no problem." I said. "Now I can't guarantee what the neighbours will think when they see you going to my house..." I grinned.

It was true - across the street from me lived one of those elderly women who seemed to know what was going on in the life of anyone, and she knew I hardly had visitors at all, even less men. So if she would see this cute young men enter my house, and us leave again shortly after with different clothes, I was sure half the neighbourhood would know within a day. But what did I care?
 
Hmmm, neighbors are a problem? I have one like that too. Well you can lead the way because i have no idea where i am going.

I turned and walked to my car as she got in hers. I started the engine and pulled out after her. I couldnt stop thinking about how i just asked this gorgous woman out. I really hope things go good tonight. I cant wait till i get some of that great italian food. Reaching for the cds i grab a favorite of mine and throw it in.

Man its going to be a great night, i said out loud.
 
I'm 40, but consider myself cute, mind if we play????

My name is Dee, and I have had real life sex with several younger men. I am interested in role playing with you if you are willing.
I have attached a picture of myself, and have many more to prove I am genuine and sincere.
This should be fun.
 
Last edited:
OOC - Hi Dee, well, it is mastaofhisown's thread, so it is his decision...

IC - I got into my car, and started driving towards my home. It was a little way, and I had time to think. It was weird how much my mood had changed. Half an hour ago I had been a bit sad, and thought I was going to spend the evening alone in front of the TV - and now I suddenly felt excited and happy. I couldn't wait to get to know the restaurant he had told me about, and, most of all, I couldn't wait to get to know him better. My mind wandered a bit and I started imagining how he would look without his clothes... I hadn't been with a 21 year old guy since I myself had been 19, I realised. Finally I was in my street, and then went up the driveway to my house.
 
I tried to send you a message but your box is to full......


It was only a short drive before we got to her house. It was quite nice. I was impressed by it. She had a nice long drive way that led up to a two story house. I was amazed at how beautiful it was. Not only was she a nock out but she had a nice house. Well actually a nice car to put in the garage of this nice house. I pulled up behind her and got out before she had a chance to shut her car off. Her window was cracked open a bit. She shut the car off just as i got to it.

"Let me get the door for you."
I almost dropped my clothing out of my arms as i reached to open the door for her. I was hoping she would like that. I was trying to show her what a gentelmen i could be.
 
OOC - yes I know... I deleted some now so there should be space again there, now.

IC - He stood by my car already when I turned the motor off, and opened the door for me. I smiled - it was nice for once to meet a guy who knew how to be a gentleman, somehow the guys I had known so far had never quite got that. He was cute in his eagerness to be nice, and to help me - I could see how he almost dropped the clothing he was carrying in his arms, and smiled a bit about that.

"Thanks."

Then we went to the door of my house, I got out the key. "I haven't cleaned up as I didn't expect anyone to see my house today," I apologized while I opened the door and remembered that the plates from my breakfast were still standing in the living room - I had to hurry in the morning and had had no time to clean them away. "I hope you don't mind."
 
If your house was to be a complete disaster then i would understand, but to have a few things laying around is no big deal. I love the way your house looks anyways. I am sure that the inside is equally beatiful as the owner and the outside of the house.

Regardless of how much of a mess it was i was just eager to get inside and change. I knew that part of me would want to just walk out naked and find her changing and take her but the part of changing in her house was enough to make my dick hard and make my heart skip a beat. As we walked through the amazingly beautiful house i asked her where it was that i could change.

Would it be ok to change in your room?

As i let out a laugh and a its just a joke comment.
 
I smiled at his comment...

"Well actually I was thinking you could change in the bathroom over there," I said, while I approached my bedroom - after all I had to change there, I had my clothes there... When I opened the door I turned back "Now if you really want to change here, you can of course." I laughed while I said that, and waited to see if he took it as a joke or serious, as I entered my bedroom.
 
Her saying if i really wanted to change in her room only made me more atracted to her. I felt a surge of pleasure run through my body. Shall i dare change in the presence of woman. A real woman and not a girl, or should i be respectful and gracefully make my way to the bathroom? I gave a moments thought to it and responded with a small laugh and said,

I am going to the bathroom where i will change. I hope i didnt upset you by not changing in your bed room.

Deep inside of me this flirtatious talk was driving me insane. i wanted her to respond with please join me, or maybe a you can look but you cant touch rule. I didnt want to push my luck thats why i purely used it as mean of joking around and seeing how far i could flirt and see how far i could test my boundries. I wanted to know she had a sense of humor and was able to laugh with me not at me.
 
I could tell he wanted me to ask him to change in my room anyway. But that would jsut be too easy. Smiling and without a word I went to my room to change, leaving him alone on his way to the bathroom. But I took care to not close the door completely, so there would still be a gap there one could look through. Once in my room, I started undressing.
 
My face flush with a slight embarrasment, i turned slowly to walk away. I could hear her shutting the door. The sqeak of the wood closeing. Only i didnt hear the door shut. As i was walking i turned my head slightly to see the door still open a crack big enought to peek in. Should i dare turn around and walk back to see if i can watch. God she was so beautiful and the thought of taking a look at her would turn me on greatly. I decided to chance it while i was at the door i would change into my cloths as fast and quiet as i could. All i had to do was put a pair of pants on and swap shirts.

As i got to the door, i positioned myself so i could see but couldnt be seen. At first i didnt see her, then suddenly she came walking out into view. She had her heels still on with her stalkings. Which i came to find out where the thigh high kind. She had a very nice black thong on to match the black thigh highs. I could feel the blood in my body flow. I unzipped my pants and let them drop and pushed them aside grabbing for my other ones to put on. I slide them up my leg while watching her. She turned slightly i could see the side of her breasts. They were being supported by a black see through bra. Her nipples were fully erect and could be seen clearly. Holy shit i thought to myself the things i would do to her.

I now had a massive erection. Holyshit i mumbled under my breath i have to get out of here before she comes and sees me. I grabbed my pants and briskyfully walked away to the bath room. I finished changing and let my erection die off before comming out. I heard Ricky's voice through the door. She was calling for me. I walked out the bath room door and down the hall way. Her door was still open the same amount as when i was spying on her. I gave a knock on the door. Responding to a come in i gave the door a push.

Through the door i stepped in. I took a look around and noticed the room was spacious. I had to take a few steps forward to actually go into the room it was like a small hall way when you open the door. To the right was a closet area and i turned to the left to find the bed. Standing facing the bed bent over was Ricky. She had her back arched and was facing me with her had and her ass out. Every thing she was wearing was what i saw. To stunded by hear beauty i just stood there momentarily. I couldnt say a word all i could do was look. Her thigh highs, heels, the black bra, the thong, danced through my body as my blood flowed to my dick...
 
I could hear him approach the door, but pretended not to notice him when I walked into sight of the gap I had left open in the door. Slowly I took my clothes off, leaving my shoes and stalkings, my thong, and my bra on. Pretending to believe myself alone, I took care to move just into the angle he could get a good view of my body.

I quite enjoyed the idea of him standing there, watching me, confused and aroused at the same time. Then I heard hasty food steps, appearantly he had left to go to the bathroom, I realized, disappointed.

But his shyness made him seem even cuter. I decided to encourage him a bit, and called out his name, positioning myself in a way that he would get a good view of me when he entered the room. Then he was there, I could see him blush as he looked at me.

I smiled. "I was wondering if you could help me decide what to wear?" I said, standing up now, so he could see me from a different angle.
 
Back
Top