Here is the long awaited second installment to my little story. Thanks for all of the nice comments and encouragement from your readers. Love ya! ***************************************************************************
Caught Again
Things have been great since I started my new job and secret life as a crossdresser. I have had a lot of experience dressing and actually passing on the street as a woman. Actually a very sexy woman at that. The visits from my supervisor were always memorable and he has taught me so much about looking and acting like a woman that I felt very confident that no one could possible know that this sexy lady had a little extra surprise in her pretty panties. Like I said, things were going good. Maybe too good. Our company contracts with the department store to provide security services. Retail stores have been hit pretty hard with the economy being the way it is. One of the cost cutting measures was to do away with store security and rely on alarm systems and security cameras instead of guards. Great! Not only was out of a job, but no longer had access to all of things that made me so happy. I did have a large stash of every imaginable item of feminine attire in my room at my apartment so I was not going go without plenty to wear. It was pretty depressing none the less to think that I may have to get a day job and wear male clothes most of the time. Little did I know how difficult finding another job of any kind was going to be? I spent every day searching the want ads, sending out resumes, and generally being miserable. Have you ever seen day time TV? OMG! After several weeks of this I could not stand it any longer. After my roommate left for work I pulled out my pretty stuff from its hiding place and started my transformation. I had all day so decided to really do it right. Scented bath. Shave all over. Scented lotion. I pulled on my panties and filled my matching bra with my silicone fake tits. Garter belt, seamed stockings, and a waist cincher. That cincher really gives me a great feminine shape. I sat down at my computer desk with my make up bag and mirror. I have become quite adept at applying make up and can change my look at will. I went for a rather slutty look on that day. Too much eye make up and even some false eyelashes. Glossy red lips and I was done. I carefully pulled on my tight black mini dress so as not to disturb the make up artistry. A long curly platinum blond wig and I am really turning myself on. Silver earrings, a dozen thin silver bracelets, and a simple silver necklace. I saved the shoes for last. Six inch red patent platform stilettos with little ankle straps. By now I am almost breathless with excitement. I stand and walk over to the full length mirror and get that old familiar feeling. I want to play with my hard cock so badly, but I have all day. I want this to last for a while. I try and watch TV, but cannot keep my mind on any of the shows. I decide to check out the Internet. I have some favorite tranny and shemale porn sites so I surf to one then the other looking for something new that I have not seen a hundred times before. No luck. Nothing new in porn town. I am now about to give up when I see a link on one of the sites that says live chat room. I have been in chat rooms many times and I find them pretty lame, but at least it has got to better then Oprah and friends. The chat room opens and I am immediately bombarded by bots trying to get me to surf to this porn site or that. There a few other live people in the room and I have a conversation with a few of them. Mostly foreign guys I think based on the way they talk. I then strike up a conversation with someone named Lucy that claims to be a crossdresser who is dressed and is also bored. I have heard this before. We chat for a while about what we are wearing and the fact that chat rooms pretty much suck. She asks if I have a web cam and well yes I do. So? "You want to cam with me?" Lucy says. I am a little afraid of this idea as I really do not know who "Lucy" is, but I am willing to risk it. The web cam application opens and I see Lucy for the first time. Not bad! I can tell that this is a guy in drag, but not really that unattractive. Lucy is all compliments about my appearance and wants to know if I am not really a woman pretending to be a man in drag. I assure her that I am not. We cam for a little while and Lucy asks if I want to see her cock. She says she will show me hers if I will show her mine. How cute! By now I am pretty comfortable with Lucy so I say OK. She moves her cam down so I can see her skirt. She raises her skirt up and there is a hard cock straining to get out of her nylon panties. She slides the panties down and her cock pops free. She strokes it a little and I can hear her moan softly. She says "Your turn." My dress is rather tight so I have squirm a bit to get in a position to get my cock out of my panties. I adjust the camera and begin a slow tease as I raise my skirt and reveal my panties. Lucy comments that my panties are so beautiful and I tell her that they are real silk just to make her more jealous. I stroke my cock through the panties and my god it feels good. It is not going to take much to make me cum. Lucy is stroking her hard cock in earnest now and I pull mine out and begin slowly stroking the length of it. I slowly pull the foreskin over the head and back again. Lucy and I go at this for a short time and I see her cock tense and begin to spurt strings of white cum. I am so turned on! I feel a huge orgasm building and just as I am about to cum I hear "Hey! Who are you? What are you doing in my apartment?!" from behind me. I am too far gone and send jets of cum on to my keyboard and monitor. I am trying to put my cock away and hide my face and would have pulled the carpet over my head if I could have managed it. Lucy quickly logged off and there I am in full drag, cock in hand, cum sprayed all about, and my room mate staring at me in disbelief. So what do you say at a time like this? The only thing that I could manage to say was "I was bored." How lame was that? My room mate starts laughing. In fact almost falls on the floor he is laughing so hard. I realize what I said and have to start laughing myself. When we both have settle down a bit he says, "I would never have know that it was you. You absolutely look like a woman. Except for that..."as he points to my now limp cock. He asks how long I have been dressing a girl. I say that it all started fairly recently. He said that he forgot his briefcase, so had to come home. He has a meeting that he has to go to, but that we need to discuss this further when he comes home. He says, "I hope that you are dressed when I get home." I am dumbfounded. All I can manage is a weak, "OK." He grabs his case and as he is leaving says "Damn, you look sexy!"
The Arrangement
After my room mate left I was not sure what to do. Everything happened so quickly that I was not sure it really happened at all. I got up from my chair, arranged my cock in my panties then cleaned off the monitor and key board. I took off my clothes and make up and put on my male stuff and went for a walk to clear my head. I walked in the park and was enjoying the nice weather and thinking what it would be like to walk in the park in my high heels. I was rocked from my daydreams by my cell phone ringtone. Hoping that it was a job offer I hurriedly grabbed the phone and said hello. It was my room mate calling. He said that he was not kidding about what he said about when he got home. He definitely wanted to see more of my female alter-ego. Well, that confirmed the fact that it was no dream. I headed for home and thought about what to wear. I didn't want to over do it and look like a total slut or some drag queen. After all I do live with this guy. Or at least hope that I would. I decided on a nice dress, modest heels, and what I seen called "day makeup" in the women's magazines. I have one dress that is very elegant. It was a designer model that would have cost a fortune if I had to pay for it. I do not own any modest underwear, so matching silk bra and panties set with garters and stockings was the choice also as I do not own any pantyhose. I finished up in time to relax a little and poured myself some wine. Right on time he was home. I stood up to greet him and all he could say was "wow". He told me to turn around with I did with ease in flats. He I took me by the hand and led me to the sofa where we sat. He said "So, tell me how long this has been going on. Did you start when you were a kid or a teenager? What sort of things do you wear? Do you ever go out dressed? Are you gay or transsexual?" I said "Whoa! You have a million questions. Would you like a glass of wine? I know I do." He said yes, so I refilled my glass and poured him one. I tried my best to answer his questions. If you have read the other parts of this story you already know the answers. When we had finished the wine, he said "Let's go out to dinner." I was shocked. I told him there was no way I could do that. He reassured me that no one could possibly know I was not a pretty girl. After a few more compliments I gave in. We had dinner and more drinks. I was a bit intoxicated by the time we returned to the apartment. He unlocked the door and as I started to enter he turned and kissed me. I have never kissed a man before, but I really liked it. I turned to him and kissed him back. Before long we were making out like teenagers. I said we better go inside before one of the neighbors sees us. We went to the couch and before you know it he was out of his clothes. I was in my bra and panties. He was kissing my neck and chest and belly and thighs. I did not stop him until he got to my panties. I said "you know what you are going to find in those panties don't you?" He replied "Yes" and started rub my hard cock through the silky material. I began to kiss his face and neck. Then I moved to his hard nipples and he let out a low moan. I asked if I had hurt him. He said that no one had ever sucked his nipples before and he liked it. I alternated gently biting and sucking them while stroking his cock. I felt his cock tense and he began shooting cum on the leather sofa. After he stopped he pulled down my panties and kissed my cock. He began to suck and lick and stroke me until I was cumming too. When we had regained some composure he asked if he had done OK. I said my god yes. Where did you learn to suck cock? He said that this was his first time, but he hoped not his last. I agreed. We both cleaned up and he asked me to come and sleep in his bed. I went an got my sexy baby doll nightie and crawled in beside him. As I lay on his shoulder he asked how my job search was coming. I told him not to ruin the moment with talk about my lack of a job. He said that in the meeting that he had this afternoon that he had gotten a promotion and a large raise. He said suppose that I stop looking for a job and become his live in girl friend. I as floored! It actually sounded great. I could dress and live as a woman and give my full attention to this man. I quickly agreed to the arrangement and he kissed me. I went to sleep in his arms. A new and wonderful life was beginning for me and I am sure the happy smile on my sleeping face showed it.