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Dee Dee Ch. 1

By: RobbyRoberts



Part 1. Meeting Mrs. D’Harley

I recall the day several months ago when I came home from school and my Mom told me that a Mrs. D’Harley from down the block had called. She wanted to know if I was interested in working for a few hours every week cleaning her pool and tidying up her yard. I remembered I could sure make use of some extra cash at the time and the only job I ever had before was delivering newspapers so I said sure, that I thought that would be neat. Mom gave me her address and told me all I had to do was go over there to find out what had to be done.

I threw my books in my room, took the piece of paper with the address on it and thought I should go there as soon as possible in case someone else got the job before me. It was a house I knew but I didn't know who lived there and some new people had moved in not too long ago.

No one answered when I knocked, so after a few minutes I knocked again, louder this time. I was just about to leave when the door opened. A woman stood there and said, "Yes?" I told her I was here about a job she had, and she said, "Oh, you must be Robby, I talked to your Mom on the phone just earlier today. Yes, Robby, I do need someone to help me with a few things but I am busy right now, I was just getting to ready to go out. Can you come back tomorrow?” I said sure, no problem but then she said, “No, No, wait, I have a few minutes so let's do it right now. Come on in for a sec, will you?" and she opened the door and beckoned me to come in.

While she was talking, I noticed that she was wearing a short black skirt that looked like it was made of leather material. It was very short, it had a slit down the front that had buttons, and some of the bottom buttons were open so that the tops of her legs were showing through. She was also wearing some black shoes that had quite high heels and some little straps that went around her ankles and the straps had little diamonds on them, all shiny, and the bottom part of her heels had the same kinds of diamonds or glass on them. At first, I wondered why anyone would have real diamonds on their shoes, but then I thought they must just look like diamonds and they probably were not real ones at all. The heels were quite high and they made her look tall, but I think that was because she was standing inside the house which was a step higher than where I was standing. I had to look way up at her to see her face, but I noticed the shoes right away because I was so low I guess. She must have been doing her hair when I knocked because she had a hairbrush in her hand and her hair was long and straight and came all the way down in front of her almost to her waist. That was when I noticed that her top was almost all open and I could see the tops of her breasts. The top was a really bright pink color sort of like a jacket with two rows of buttons but it was only buttoned below her tits and I could see she was wearing a black bra that pushed her breasts up quite a bit. When I looked back up at her, the sun shone on her for a moment and I thought I could see her nipples through the bra but I am not sure.

I went in and followed her to the living room where she told me to sit down. I could see that her hair was long and went all the way down her back. She sat down opposite me and when she did, she crossed her legs. Her skirt was so short that when she did that I could see the tops of her pantyhose where the fabric changed to a different color and thickness. She was beautiful. I think I turned very red because I think she knew I was looking at her legs and her shoes. I was fascinated by how high they were and I couldn’t take my eyes off them.

She asked me if I was interested in working three or four hours a week cleaning her pool and doing odd jobs and if I could come after school and sometimes on the weekend and other questions that I don't even remember. I think I just answered yes to everything because when she was talking to me she bent forward a little bit and her jacket opened more so that I could see part of her tits. I could not see all of them but quite a bit. She didn't even seem to mind that I was staring and she kept asking me questions and every time she asked me if I had any questions I just said no.

I remember her telling me that she preferred to be home when I came over and if Tuesday and Thursday after school were okay days for me because she was usually home on those days and I said sure. Then she said she could show me where a few things were right away if I wanted and I said okay. Anything was okay because I just wanted to keep looking at her and I could still see some of her tits. Were they ever neat and when she got up I realized I had a hard on and then when I got up to follow her I tried to adjust my pants so it wouldn't show.

I followed her to the back door, watching her walk in those high heels, and when she got to the sliding door she bent over to undo a latch. When she did, her skirt went up higher on her legs and I saw that she was wearing garters and stockings, and not pantyhose like I thought. The tops of her stockings were clear right before me. Wow, I had only seen those in pictures, never in real life before, and I often jerk off looking at pictures of girls in garter belts and high heels and I think my cock got even harder.

She turned to tell me we were going to the garage and I think she had to have noticed my hard-on but she just smiled and went out and I followed her. She went into the garage and started to show me where she kept the pool equipment and the gardening tools. I followed her again and got another chance to watch her walk in those heels. I couldn't believe this was happening to me.

In the garage she showed me a few things and a couple of times she bent over to pick something up right in front of me and when she did I could look down the front of her jacket and see some of her tits. They looked so neat. The only tits I ever saw in real life were my mom's once by accident and they were neat too but not sexy like Mrs. D’Harley's. I have a girlfriend sort of and I have squeezed her tits and felt them but I have never seen them. It was a little dark and I could not see too well but I tried to keep moving around so I would be in front of her whenever she leaned over.

Then she said that some of the pool things were kept on a shelf and she got a small folding stepladder out to show me how to get them down. She opened it and then started to climb it. When she got to the top step, her bum was above my eyes and when she reached up I could see the tops of her legs and her bum and how her garters were attached to her stockings and went over her bum and disappeared. It didn't look like she even had any panties on because I thought I could even see part of her pussy but it was from the back and the light was dim so I am not sure. Maybe she had on some thong panties that went into the crack of her ass, I don’t know, but I did see a lot of her bum and it sure didn’t look like she was wearing panties.

I told her I thought I could find everything okay, and when she climbed back down she put out her hand for me to help her. That was the first time I touched her. When she stepped off the last step, she tumbled a bit and fell against me, and I am sure I felt one of her tits on my arm, but it scared me so much I pulled my arm away. When I pulled my arm away, it must have caught her jacket, because it came undone a bit more and I could see even more of her bra. It did not even seem to bother her; she just adjusted it and smoothed it out.

She asked me if I wanted the job while we were walking back into the house and I said sure. She then asked me what I thought would be a fair wage and I didn't know what to say, so I said it didn't matter and I meant it at that point because I think I would have worked for nothing if I could see her again. I think I was even in love and I had a hard time trying to hide my hard-on. I kept my hands in my pockets and pushed out the front of my pants thinking it would help.

Then she walked me to the door, saying she was in a hurry but asking if I could start on Tuesday and I said sure. She said great, then gave my arm a squeeze and said she thought it would work out fine us working together and said she was looking forward to seeing me again. She also told me I could call her by her first name, which was Dee Dee, if I wanted to, but it was okay to call her Mrs. D’Harley if that is what I felt most comfortable with. Just as I was about to leave she asked me if I thought five dollars an hour was fair. I was hoping for two so I was overjoyed and said that was fine, as nonchalantly as I could. She gave me a big smile, and then she bent forward to pick up a newspaper that was on the stoop. This time I could really see more of her tits because her bra was a little loose, the sun was behind me and very bright, and they looked like the nicest ones I had ever seen, in pictures I mean. My mom’s were pretty big and these looked big too. Then she smiled and said goodbye for now and closed the door and I was left standing there with a hard-on.

There is a park on the way home so I went in there and found a spot I sometimes go to and I jerked off thinking about Mrs. D’Harley's tits and her legs in the stockings and the way she walked in her high heel shoes. I think I shot the biggest load in the history of mankind. When I got home, I went to my room, lay back on my bed and jacked off again, with the vision of her clearly in mind, just as if she were right there before me. I even did it again that night when I went to bed and the next day in school, I asked to be excused twice to go the washroom and each time I went into a stall and jerked myself off thinking about her. All I could think of was Tuesday when I would see her again, and after a lot of internal debating with myself, I decided it might be best to jerk off again just before I went over so I wouldn't get a hard-on when I was there. I couldn't wait till Tuesday.

Dee Dee Ch. 2



Part 2. My First Day

On Tuesday, I rushed home after school and told my mom I was going over to Mrs. D’Harley’s to start work. I said I was going to have a shower first and she asked me why I was going to do that before work rather than after. A good question I guess, because I got all flustered and didn’t know what to say. I guess I subconsciously thought I should be clean in case something happened when I was there although I knew that was stupid. But I remembered I thought I should jerk off again before I went so I wouldn’t get a hard-on when I saw her again. So I had a shower and yes, I jerked off in the shower thinking about what she looked like in the garters and what her breasts looked like when she bent over in front of me. I put on the tightest underwear I could find thinking it would hold my erection in so it wouldn’t show if I got one again.

When I rang the bell, she answered it right away and told me to come in, that she had been waiting for me. I couldn’t believe how she was dressed. The first thing I did was look at her feet, and sure enough, she was wearing some high heel shoes again, though this time they were bright white ones with open toes, little straps around her ankles and a little design with holes above her toes. The heels were quite high but I don’t think they were as high as the black shoes she was wearing the first time I saw her. She had on the shortest pair of cutoff denims that I have ever seen. They seemed to go right to her crotch. What really took my breath away though was that she was wearing black silk stockings that only went about half way up her thighs and they were held up by some garters that came out of her shorts. She was also wearing what looked like a man’s white shirt that only had one button done up, right in the middle. It was open all down her front and she was wearing another black bra, but this one was lacier and had a little strap holding the two cups together so I could see some of her tits again. 

When she turned to lead me in, I could see the other pair of garter straps coming out of the back of her shorts. They circled around her bum and down to her stockings in the most erotic way. I noticed that the tops of her legs were a little bigger that I remember the last time, but they looked so neat in the stockings I couldn’t take my eyes off of them. Her shorts were so short that I could see just the edge of the tiniest panties I could imagine, right in the crack of her ass. They must have been thong type panties because I could hardly see any of them.

When she went to the couch across from where she motioned me to sit, she sat on the arm of it for some reason, rather than right on it. When she did, her legs straddled the arm and I could see all of her legs, and even her panties around the edges of her shorts. I am sure she knew I was looking at her legs but she didn’t seem to mind, in fact, she kept shifting and trying to get comfortable and every time she did, I could see more of her panties. I think I was turning red again and I could feel my cock getting hard and I was mad thinking that I masturbated for nothing. She looked even more beautiful than I remembered, though, even though she was as old as my mom was. I looked at her face and I could see some wrinkles under the makeup, but she was so neat looking. When I finally was able to take my eyes off her legs and her breasts, I also noticed she was wearing a black collar, sort of like a choker. I thought that it looked really neat.

She started to ask me questions about my interests and how I was doing at school and stuff. After a while, I said I should probably get started and she said not to worry, that she would pay me for the whole time I was here, even when I was only chatting with her. She said she lived alone and that she missed having company and asked me if I would mind chatting with her once in a while. I told her no and she said she was interested in young men and what they did and thought about and did I mind answering her questions. I told her no that was okay; that I would try to answer any type of questions she had. She kept shifting on the sofa and I kept staring at her legs and wondering how she ever managed to walk in shoes that had heels that high. I thought she was the most beautiful woman I had ever seen. I think I could have stayed there looking at her forever. I don’t remember if my cock was hard or not but it must have been. At least I was sitting so she couldn’t see it. Then she got up and shifted to sit right on the couch and when she did, she turned a little to the side I could see a little bit of the top of her tits. Earlier I thought I could see a little flower pattern in her panties and now I could see a pattern in her bra so I wondered if they were a matching set. I remember thinking how neat that was. We kept talking for a few more minutes.

Finally, she said I could start by cleaning the pool. She told me she was going to change into a swimsuit so that she could show me how to do it and that I should start by getting the equipment from the garage. I said sure and went out to do that. A little while later, I heard her call my name through the kitchen window. When I responded, she asked me if I could come in for a minute.

When I went into the house and I saw her, I couldn’t believe my luck. She had on a bikini and she had on another pair of high heel shoes. They were red and they had really high heels. She looked so neat. The bra part was quite wide and seemed to push her tits up and out and they looked so cool. It was a kind of red and pink or purple kind of material and it was wide where her tits were so that there was a lot of cleavage showing. A strap that went around the back of her neck held up the top and the bottom was not like a thong or anything but it was quite high on her hips and I could see all of her legs.

“Robby”, she said, “I just bought myself a new bathing suit and I wanted to know if you thought it fit me okay and looked good on me before I wore it outside. What do you think? Is it okay?” And with that, she started to turn around and pose in it so I could see it from different angles.

When she stood towards me and bent forward a bit, I could see almost all of her tits. And her legs looked so long and sexy in the high heels. 

“Well”, she said, “what do you think? Does it look okay on me? I am such a poor judge of what looks good on me.”  

“I think it looks great on you, Mrs. D’Harley,” I said. “Are you just saying that to make me feel good Robby, or do you really mean it?” “No, no, I think it looks great on you.” “That is sweet of you to say, Robby, thank you, you are so sweet.”

I don’t know if she noticed how red I must have been or if she noticed that I had a hard-on or not, but she just smiled, adjusted her tits in the bra part and said, “Okay, I’ll wear it. Let’s go and I’ll show you how to clean the pool.”

I followed her out, watching her walk in the heels and my hard-on got even bigger from looking at her bum and her legs. Somehow, I got myself under control and after a few moments, she told me I was getting the hang of it and I should be okay on my own. She said she was going to go into the pool to cool off while I finished.

After swimming a few laps, she got out and because her suit was wet, it hung lower on her hips and her tits and I could see them almost as clear as day because the fabric was wet. She went over to the diving board, which was right across from me. I was pretending not to notice her but I couldn’t keep my eyes off her, and I had to keep the vacuum in front of me to hide myself. She posed on the diving board, then dove in head first, and then swam across the short distance to the ladder where I was standing. When she climbed out, her tits were out of her suit. They must have come out from the pressure of the dive and I guess she didn’t notice. I could see her bare tits right in front of me. They looked so neat and firm. They weren’t as big as I thought they were, maybe because the bras had made them look bigger and I was using my imagination too much, but they were a really nice size and I thought they were the nicest ones I had ever seen. She saw me staring and looked down and when she saw her tits were loose, she just said, “Well, I’ll be damned” and then she just pulled her bra cups up over them as if nothing had happened. She stood there and adjusted her tits and her bra right in front of me, then walked around to the diving board and dove again.

When she got to the ladder and climbed out, her tits were out again and when she noticed, all she said was “damn” and started to put them back in and adjust the suit again. It happened a third time but that time she also stopped and tightened the string that tied behind her neck. Her tits popped out like that two more times, and then she asked me to help her tie the strings behind her neck so they would be tighter. I said sure but I was shaking so much I had a hard time. When I was tying the bikini straps, I got to touch her skin and it felt so soft and smooth. I let the straps slip out of my hands once hoping the bra would fall right down but she was holding it onto her tits with her hands.

After I tied the straps, she dove again and the same thing happened. She swore again and said that her damn bathing suit was useless and a nuisance, so if I didn’t mind, she was going to leave the damn top off. I tried to look away and when I next saw her she was walking to the diving board and she didn’t have her bikini top on. Her tits were firm but they jiggled when she walked and they looked so gorgeous. I didn’t know what I was doing about cleaning the pool so I just pretended I did and kept working and watching her when she didn’t think I was looking. After a few more minutes of swimming, she started to dry herself off and it was so neat watching her dry her tits and her legs. Then she put her high heels back on and walked over to the side of the pool that I was now on, but she still didn’t have her top on.

“Here, Robby, let me show you how to do that to make it easier.” She walked over, took the rod from me and proceeded to demonstrate how she wanted it done. The only problem was that she was standing topless right beside me and I was looking at her tits, not at what she was doing. She gave it back to me and told me to try it again. Because I wasn’t watching intently, I didn’t get it right and she moved closer, took my hand and my arm to help me, and when she did, one of her bare tits brushed against my arm. At least, I think it did but I am not sure. Then she said that was good enough for today, and told me to come on in the house when I was finished putting things away.

I put the equipment back in the garage and then I went inside the house. I knocked first and heard her tell me to come in. When I did, she was talking to someone on the phone. She motioned for me to sit down and after I did, I looked over and she was still topless. I heard her ask for an address and a time, and she wrote them down. After a pause, she said yes a couple of times, then told the caller that she couldn’t talk about that on the phone. She said that she would do what the caller wanted and that everything would be fine and that she was sure that the caller would be more than satisfied. 

After the call she told me that she had to go to work for a while and that I would have to excuse her in a moment. I asked her what kind of work she did and she said she was an entertainer. I somehow visualized that she was a musician, and for some reason I didn’t say anymore.

She stood up and stopped, then said, “Robby, did it bother you that I took my top off out there?" “No, no, of course not, Mrs. D’Harley.” “I suppose a young good looking young man like you sees a lot of nude girls, don’t you?” “Yeah, sure,” I lied, and then thought it wasn’t a real lie because I did see a lot of them in magazines and on the internet, only not in real life. “Well, I hope I didn’t embarrass you but that damn top just kept slipping off and it was making me mad. I am going to have to return it, I think. What do you think I should do, take it back?” Gee, I don’t know, Mrs. D’Harley, it is sure pretty, I think it looks real neat on you. It’s too bad it doesn’t fit too well.” 

What do you like about it, Robby?” That question caught me off guard and I didn’t know what to say. “Well, I just think it looks nice on you, I guess, I’m not sure what it is, but it seems to suit you, I guess.”  I somehow stammered. “Thanks for being so honest, Robby, you are sweet and I appreciate it. Anyway, I think I should go and get ready. Will you be back on Thursday?” “Sure, Mrs. D’Harley, Thursday will be fine. I’ll see you then.” “You know Robby, I think perhaps I should give you a key to the garage. My work hours are unpredictable and if I am not here, then you can still do some work if you can get into the garage. If I am not here, the door from the garage to the kitchen is always open so feel free to get a drink from the fridge or to use the washroom if you need to. Just a minute.” Then she went into the kitchen and got a key. She came over a gave it to me and again she was standing topless right in front of me and it didn’t even seem to faze her at all, she just acted so normal. After I took the key and put it in my pocket, I started for the door.

“If you don’t mind, I won’t see you out today,” she said, “seeing as how I’m dressed, I mean undressed.” And she laughed a little and smiled at me. When I turned around to look at her, she was standing up tall on her heels, and she had pulled her shoulders back so that her tits were standing out like bullets and she was staring right at me. I stared at them, smiled sheepishly, and then turned away embarrassed. She said, “You like them, don’t you Robby?” I nodded yes, then she just smiled and said, “Okay, that’s nice, I’ll see you Thursday.”  They really were neat. They weren’t huge or anything, but they had such a nice shape and they looked so soft. The brown areas around the nipples were not very big like some of the pictures of other tits that I saw, and her nipples sort of pointed outwards from each other and downwards a little bit too. I could even see some blue veins that ran through them. I just kept staring at them and she just stood there in front of me with her shoulders pulled back and they looked so wonderful. She smiled at me again and finally told me I should probably go since she had an appointment and had to get ready. She said she would see me again in a couple of days.

I closed the door and skipped away down the street, feeling unbelievably light headed. Guess what I did? Yes, I went right to the park again and jerked off, thinking about her tits and remembering what it felt like when one of them brushed against my arm. I jerked off again twice that day and the next day at school and could not take my mind off her. I didn’t learn anything at school and didn’t even want to talk to anyone about anything because I couldn’t keep anything else on my mind but Mrs. D’Harley, I mean Dee Dee. Well, I did think about time and how soon Thursday would come around so I could get back there and see her again, of course.



Dee Dee Ch. 3



(Copyright, October 10, 2001 by Robby Roberts)

Chapter 3: Thursday

On Thursday, I rushed home after school, had a shower, jerked off in the shower thinking it would help prevent me from getting a hard-on when I saw Mrs. D’Harley again and took off for my new job. 

When she answered the door, she had the most amazing negligee on, a sheer red one that I could see right through. I stood there mesmerized looking at her and she asked me if I liked what she was wearing. I said I sure did and told her I thought it was beautiful and when I did, she sort of stood there and posed in it for me. I was sure she was not wearing a bra. The negligee, at least that is what I thought it was, had the tiniest little straps holding the top up. The top part sort of covered her breasts but it was lacy and transparent. I looked at her feet and she had white heels with a strap that went around her ankles. She was standing there in front of me, and the fabric was clinging to her legs. She had her legs spread, I could see them through the sheer fabric, and I am sure she didn’t have any panties on at all. I could see right through the material and I could see her pussy almost as plain as day. At least I thought that is what I could see. My imagination was probably helping me a little bit. I noticed that she had a matching necklace and earrings with red in them and this time her hair was all frizzy so it didn’t look as long as I remembered it the last two times I saw her.

She didn’t even seem to mind, and when she saw me staring, she smiled at me and asked me again if I liked her outfit. I said yes, I did and she said that she would wear it again for me some other time because she thought of me as someone who had a good eye for women’s fashions and she liked to model for me. I said great, and then she told me that she had to go to work for a while. She said she would be gone for two to three hours but that I should just go ahead and work without her being there. She asked me if I needed her, and I wanted to say yes I did, but I said no, I thought I would be okay on my own. She asked me if I had my key to the garage with me and I said yes, and she just said okay, that she might not see me at all that day because I would probably be finished before she got back, then she excused herself and closed the front door.

I stood there for a minute or two totally mesmerized by what I had just seen, as if I had seen a mirage or a miracle or something, and then I noticed I had a hard-on as big as a telephone pole. After a minute, I walked around to the back yard, opened the garage door, started to get all of the equipment out, and then started to work. My mind was full of mixed emotions, mostly cursing my bad luck at her not being home and thinking I would not be able to see her and I would have to wait almost a full week before I saw her again.

In a few moments, she came out to say goodbye. She looked different because she was dressed in the weirdest outfit I had ever seen. She sort of looked like a little kid or a schoolgirl or something. She said she needed my opinion on her outfit before she left. I looked at her and the first thing I noticed was that was wearing little short white socks over her black nylons. They looked like they were rolled down and had little frills around her ankles. Her shoes were black and had high heels but they weren’t as high as the other shoes I had seen on her. They were pumps and didn’t have any straps or anything but I thought they looked sexy just the same. Her skirt was like a tartan, all black and white squares and lines and was very short. She was also wearing a white blouse that looked like it was made out of sweater material. It wasn’t done up so I could see her bra, a white one that looked like it closed from the front because it had a little strap with a snap on it between the cups. It was lacy around the edges and it looked firmer that the other bras I had seen her in and I couldn’t see as much of her breasts as the other times, but it looked really neat anyway. Her outfit reminded me of the types of outfits that some of the girls in our neighborhood wear when they go to school, at least the ones who go to private school and have to wear a school uniform.

She stood in front of me, spread her arms out, smiled at me, and asked me what I thought of her outfit. Then she turned around and her skirt was so short I could almost see her bum. I told her it was really cool, and I thought it was 

She said she had to leave to go to a meeting and she wanted to be dressed nice for it and that she trusted my judgment on what she wore. I wondered what type of meeting she was going to when she was dressed the way she was. She asked me if everything was okay and said she might not be back before I left but that she would see me next week, then started to walk toward the garage and I was left alone, feeling sorry for myself. It sounded kind of weird to me but I didn’t say anything. I just watched her walk to the garage, and she must have known I was looking at her because she was walking like one of those models that I’ve seen on television. You know, where they put one leg in front of the other and sort of sashay when they walk, wiggling their asses to attract attention. Of course, I didn’t mind, but when she got to the door of the garage, she turned around quickly and caught me looking at her instead of working. She didn’t seem to mind though, because she just smiled and blew me a kiss over her hand, then turned and disappeared into the garage.

I remember wondering what it would feel like to walk in shoes that had high heels and wondering if I would be even able to stand in them or not. She seemed to be able to walk okay but it sure made her legs look neat. For some reason her legs looked a lot better when she was standing in high heel shoes than when she wasn’t wearing any like when she was swimming on Tuesday. She looked really neat and beautiful and I was sorry that she was leaving. 

After working for twenty minutes, I had to pee and wondered if I could wait till I got home, then remembered Mrs. D’Harley told me I could use the bathroom in the house and that the door from the garage was usually unlocked. I had to go real bad so I decided to try the door and sure enough it was unlocked. I took my shoes off and headed for the bathroom, then wondered if there was also another bathroom off her bedroom and decided to use that one instead. I also wondered what her room looked like so I headed that way. Sure enough, there was a large bathroom there and I went into it. I decided I should sit down to pee so I wouldn’t make any splashes that she might see because I didn’t want her to know I was in her room. There was a big Jacuzzi tub in the corner and it had big brown tiles that held a big purple tub. I wondered what it would be like to see her totally naked in that tub and I thought about being in there with her having a bath together. 

When I was finished and walking out I noticed some of her clothes strewn on the bed, a bra, a pair of panties and some stockings. Her red negligee was also on another part of the bed but when I looked, there weren’t any panties with it so I thought that maybe she really wasn’t wearing any and I really did see her pussy. 

I was curious about how big her tits were, so I looked at the bra to see if I could find a tag on it but I couldn’t. I then thought maybe one of her other bras might have a tag so I went over to a large dresser and opened the top drawer very carefully. There weren’t any clothes in it, but there was a box of business cards in it and I took one out to look at it. It was very plain and it had her name on it, Ms. Dee Dee D’Harley and her phone number at the bottom. Under her name it said, ‘Escort for gentlemen of distinction’ and under that it said ‘sophistication and discretion’.

Beside the box of cards was a folded part of a newspaper with one of the want ads circled in red. I picked it up and read it. It said, ‘Dee Dee, an angel who will cater to your every whim, make every one of your fantasies come true and pamper you the way you always wanted to be pampered. A mature brunette and busty beauty to cater to your every need. More expensive perhaps, but classier than the rest. Discretion assured. Out-calls preferred and only by appointment. 5 p.m. till 3 a.m. Call 456-892-9999.’ The rest of the ads on the page were all for other escorts and massage services and the page was from a local paper that was available for free downtown and had a lot of those types of ads in it. I remember seeing a copy once or twice and being fascinated by reading all those ads and wondering what kind of people did that and just exactly what they did. I even called one of the numbers once but when I asked the woman if I could fuck her she just hung up and I was too shy to try another number.

Did that mean that Mrs. D’Harley was a prostitute, I wondered. Wow, I thought, and remembered she told me that she was an entertainer. Then it started to dawn on me what kind of entertainer she was. My emotions started to get the better of me and I can’t recall if I was excited or disappointed at that point. I started to feel guilty about snooping and was about to leave so I put the card and the newspaper back as carefully as I could.

Then I remembered that I still didn’t know how big her tits were. Whenever I thought about them I used numbers that ranged from 36 to 38 and cup sizes from C to DD although I knew the latter was not quite correct. I opened another drawer to look for a bra but this one was full of artificial cocks and things. Some were so big I couldn’t believe it. Some were hard and heavy and had switches so they were vibrators I guess, and others were soft and rubbery and almost real looking and feeling, but they mostly seemed to be too big to actually fit inside anybody. There were also a bunch of other things in there, even some handcuffs and chains and different kinds of pinchers and clips. I was starting to shake and I was very nervous, trying not to disturb anything so she would not know I was in her room. I couldn’t decide whether I should leave or not, but I was so fascinated I looked in her other drawers too.

She had all kinds of sexy underwear, bras and bikinis and frilly underwear. A whole lot of garter belts, stockings, and other things that I didn’t know the names of, teddies and girdles I guess, but I didn’t know why she would need a girdle because she looked so shapely to me.

When I was about to leave, I decided to look in her closet. It was a big walk-in closet and when I looked in, it looked like there was about 20 pairs of shoes, mostly with high heels, and all different sizes and colors. There were even some really long boots that had high heels too, some with laces and they were different colors also. I went in and touched one of the boots that looked soft and it was really soft leather, like a pair of good gloves. I thought they must cost a lot of money.

And of course there were all kinds of dresses and suits hanging up but I didn’t touch any of them. There were even fur coats. I thought that she must be very rich, and that she must make a lot of money being an entertainer.

There was a trunk in the corner but it was locked and I couldn’t open it but I wondered what must be in there. When I was about to leave, I noticed a clothes hamper by the door. I took the lid off and it was full of dirty clothes. After looking at all her stuff and thinking about what she would look like in some of it, I had quite an erection. I felt I needed to jerk off or I was going to explode. Then I thought she would never know if I touched some of the clothes from the hamper because they were all messed up anyway, so I started to take some of them out. The bikini that she wore on Tuesday was in there and I picked it out to feel it. Then I smelled the panties to see if I could smell any of her on it. 

I couldn’t so I took some more clothes out, finding several bras and one of them had a tag that read 36. Wow, I thought, now I knew one of her secrets, how big her tits were, and then I took my cock out of my pants because it was so hard and starting to hurt me. I started to smell her panties and one pair really smelled a lot, so after smelling them I wrapped them around my cock and started to jerk off with them. They were silky and felt so good and then I found a pair of her nylons, wrapped one of those around it, and continued to jerk myself off. I soon went back to the panties because they felt better around my cock. Before I realized it I started to come and I didn’t have enough time to catch my sperm. I came with so much force that I splattered on the hamper and on the wall behind it. I tried to catch it with my other hand, but some of my sperm got on the panties that were around my cock and on the stocking that was on the floor. At least the stocking stopped some from getting on the rug, I thought.

I started to panic thinking she would find out someone was in her room jerking off in her stuff. I was shaking like mad. I found some tissue and wiped up everything I could see, but some left little marks and there was a big wet spot on the pair of panties that was around my cock. No matter how much I tried to dry it, I couldn’t and I considered whether I should steal them or not, then decided that if they were one of her favorite pairs that she would notice they were missing, so I couldn’t very well do that. I dried them as best I could then when I put things back I tried to place the panties in such a way that the wet spot wouldn’t show, and I thought maybe she wouldn’t notice, and that maybe they would be dry before she did the washing. Then I remembered that semen left a stain on my own shorts and that she would notice for sure, so I took them into the bathroom and ran a little water on the spot and rubbed it. When I tried to dry it with some toilet paper, a whole bunch of little pieces of the paper got all over the panties and I couldn’t get them off, so I started to panic even more.

I started telling myself how stupid I was and then started to think that I better get out of there before she got back or before I did something else that was stupid. Not knowing what else to do, I left after trying to leave everything the way I found it, and went back outside to work. I worked for a little while, and then decided I should get out of there before she came back so I wouldn’t have to face her in case she asked me any questions if she suspected what I had done.

I couldn’t sleep that night at all. My mind wandered all over the place. For a while I would think about what she would do and what she would think of me if she found out I was snooping in her things. Then I would think about what she did when she was working, and what kind of fantasies she meant in her ad. Once in a while a picture of her entered my mind and when it did I could see her tits and her legs and her high heels all so clearly, and whenever those images entered my mind, which was almost every waking minute, I jerked myself off. The only other thing I thought about was whether I was doing any long-term damage to my cock as a result of all the masturbating I was doing these days.

Whenever I thought about going back to her place next week, part of me panicked thinking that she would obviously know what I had done. Then another part of me tried to calm me down and say that she would never know and I should go so I could see her again. Every minute of the day seemed to be consumed with thoughts of her, how beautiful she was, but how mad at me she would be if she found out how stupid I was and what I did. The best parts though, were when I put those bad thoughts out of my mind and concentrated only on her body and her neat tits, and when I did that, you can probably guess what I ended up doing.