tagFirst TimeDee Dee Ch. 3

Dee Dee Ch. 3

byRobbyRoberts©

(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.

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