Bob
Cindy just called and said she would be home a little late tonight. I know what that means, another night out with her boss Randy. I don't know how I've let this go this far. I know I'm really turned on watching Cindy make love to another man. I noticed over the weekend when I fucked Cindy, she wasn't as tight as she's been all these years. This guy Randy sure has a log hanging between his legs. Cindy maybe stretched permanently. At least as long as her boss keeps fucking her. I thought this was supposed to be for the two of us. I don't even get to see what's going on at the hotel they will be meeting for there little fuck. I'd sure like to find some way to watch them without them knowing I'm around.
I'm glad the girls are spending this week with there Grandmother. I can't even think straight knowing Cindy is going out with Randy tonight. I really don't know how to explain my feelings. I have a trophy wife I should be proud of and yet I'm excited about her fucking another man. Yet, I also feel some jealousy that Cindy will be fucking this guy tonight. 
At least it gives me time to myself to play on the Internet. If only Cindy knew of my little secret about dressing in woman's clothes when she's not around. At least she has no way of finding out about my web site with my pictures posted. If she ever did, she would kill me for sure. I'd taken the chance last week of shaving my legs and Cindy didn't even notice. She's been so wrapped up in her new lover Randy. 
Dressing in woman's clothes has been a long time fetish of mine. I'm able to keep some things in the attic where Cindy or the girls wouldn't find them. I've never been a big man, of coarse a lot bigger than Cindy's size 5 dress. I learned from trail that I could fit in a size 12 dress and 9 heels. I would hate for Cindy to find all my things. First thing she would do is think they belonged to someone else. 
I wonder if I could pull it off by following Cindy one night during one of her hotel encounters. It excites me just setting here thinking about the idea of Cindy not knowing I'm around and watching her fuck her stud. I'd have to work fast if I'm going to pull this off tonight. I would have to shave my face or better yet, use hair remover and do my nails and shave my legs. Lets see, I have about 4 hours before Cindy gets off work and I'd have to get ready than drive over to her office and park somewhere so she can't see me. Plus I have to worry about the neighbors seeing me leave dressed as a woman. If I can back the car out of the garage without anyone around here seeing me I'd be fine.
Let me get my things and get ready, I could wear the tight black dress I bought last month and black heels and the blonde wig. I think I have just enough time to pull this one off. I better start with a shower and maybe I can shave my legs while I'm in there. Well, maybe the hair remover on my face would be better to start with, it takes time to work. I'll have to work on my girl voice if I encounter someone while I'm out. I couldn't even imagine Cindy finding out about my little fetish.

Randy
I can't believe my luck being hired with this firm, and how lucky I've been to meet Cindy. I sure wish she didn't have an old man around. I could fall in love with a woman like this. Its been a few years since my college days that I fucked some of these white women on campus. Cindy is different. I don't understand why her husband lets her get away with all this. I know he's got to know she'll be with me tonight. Cindy said he had a fetish and wanted to see her get fucked by another man. I thought it would be a one time thing. I'm not going to let this little woman get away that easy. No sire, I'm going to make sure she is well hooked on this old cock of mine. 
Good lord, how tight this woman is when I'm inside her. She feels like a virgin every time I'm deep inside her. Cindy lets me know how good it feels by squeezing tight. It almost feels like a vise grip. Her husband can't be feeling what I feel anymore. If he ever did for that matter. He looks like I did when I was 8 years old. Better for me. When I'm done, Cindy is going to keep that little cock cage on that guy at all times.
Wouldn't that be a thought! Keeping the cage on him all the time and me holding the key. That would suite me just fine. At least I'd know my woman was horny and clean when we fucked. 
I think I'll work on that starting tonight and see how Cindy feels about me holding the key to the cage. We'll see tonight.

Cindy
I never thought things would get this far with my boss. I thought it would be a little fun being able to fuck another man. Besides I have a husband that agreed to let me fuck my boss. I just hope things don't get out of hand. I have to admit, Randy has sure treated me nice ever since he transferred to this office. His cock feels so good inside me. Bob has never made me orgasm like Randy. Randy's cock is so thick and he can move around the right spots. Bob is a lot smaller man than Randy in more ways than one. I use to tease Bob about how his body size was about the same as a lot of women I work with here at the office. If feels so good when Randy puts his big arms around me and holds me tight. He's just a big hunk of a man. A black man at that! If my mother ever found out I had fucked a black man. I don't really know what her reaction would be. 
I'm not sure how long Randy plans to stay here at our office. Something was said when he came that he wanted to see how everything worked out in this location. Having Randy around at work is going to make it very hard not to want to fuck him. What about my husband! How much will he put up with before he feels its going to far.
Anyway I have a date with Randy tonight after work. It will start with dinner and a couple drinks and most likely end up at a hotel. I have to admit I'm really looking forward to tonight. There is something more than just fucking Randy, I can't explain it right now. I almost feel like I have these feelings for him other than sex. When he touches me I seem to just melt in his arms. I love my husband and I know I shouldn't be feeling like this but I do and I can't help it. 
I think I'll change into the dress I bought with me this morning. Randy loves my legs and the dress is very short. I couldn't wear anything like it here at the office, I'd get too many dirty looks from the other woman here that's for sure. I have my higher heels I can put on and maybe I won't wear anything under the dress. Nobody will notice I won't have on a bra. Only Randy, and he won't mind. I don't think I'll wear the panty's either. They will only show through the dress. I shaped my pussy hair like a little heart. I wonder if Randy will notice tonight. After all I did it just for his pleasure. There I go again, I'm doing special little things for Randy. I brought his favorite perfume and plan on putting just a trace where I know he'll find it. I'm getting wet just thinking about tonight. Having his thick cock sliding inside my pussy. I've never felt that good with a man before. I wonder exactly what it is about him. He really knows how to make love to a woman. I plan on showing him how hot I can be in bed. I don't think I can even wait until tonight. 

Bob
Now if I can only pull up these panty hose without getting any runs in them, yes that's it. A little further, yes! Got them up! This dress fits a little tight for a 12. Putting some padding in my bra sure helps with my girlish figure. That wig took me for ever to get in place. I even had to pluck my eyebrows to look a little more dainty I would say. The fake nails look nice and straight. I don't know how Cindy gets her hose up with her long nails. I suppose after years of practice I'll get the hang of it. Now for the heels. These straps are a little lose. I think I need to tighten them a little before I fall down on my ass. That's all I would need to happen while I was out like this is to make a fool out of myself and getting caught by someone. Maybe even getting beat up by some guys. Now, lets try the purse. Ready! Even my lipstick looks natural. I could pass as a real blonde housewife.
Now I better get the car out and go before I'm late. I hope none of the neighbors are out as I'm backing out of here. I'll have to get use to these heels, I better slid them off for now until I get over to Cindy's before I get into an accident with them on. OK, now for the garage door opener. Here we go, easy now. All right nobody is around. I'm in the street and ready to go. First stop sign, yes I've made it past our block. Now, until the main highway.
OK, pulling around the corner near Cindy's office building. Here is a good place to park right next to this van and I can look through the windows and see directly over at the front door where Cindy and that Randy boss of hers will be coming out soon. I can see her car in the lot parked right next to his car. Only a matter of time now.
Looks like almost everyone has left there building. I bet Randy has to lock up since he is the manager. Yes, here he comes now. Boy, look at how tall this guy is even from a distance he looks like a giant. He seems to be holding the door open for someone. There is someone in a short black tight dress coming out. Its Cindy and she doesn't have the same dress on she had on when she left the house this morning. He's locking the door now. Putting his arm around her as they walk to the car. She's passing her car and walking toward his now. They're stopping now.
Cindy is putting her arms around him and he is bending down to kiss her on the lips. Look at that, 2 minutes now. What's wrong with them, someone may still be around. He has his hands cupping her ass now and Cindy looks like she is pushing her body into his. Look at that, she just reached down between them and stroked his cock outside his pants. 
He is opening the door for her now and she is getting inside. Closing the door and getting inside himself now. It looks like Cindy is bending over to kiss him again. They are backing out now. I better get this thing in gear if I'm going to follow them.
We are on the highway now and I'm trying to keep up with them just enough not to lose sight of them. OK, they are turning into the hotel parking lot near the office. I see a bar next to the hotel. Randy is getting out and going into the office. 
OK, looks like he has the card key in his hand. He is pulling the car over a few spaces. Randy is getting out again and going over to open the door for Cindy. Cindy is getting out and Randy is reaching for her hand. They are kissing again right here in public. They are walking over to the bar and going inside.
Now I got to make my move if I'm going to watch them tonight. Let me get this car parked on the other side of the bar and go in. I hope I can pull this girl thing off tonight.