First time dressed outside. (Part I)

First time dressed outside. (Part I)It was a bit awkward getting into the bus and looking the driver into his eyes while I showed him my ticket, but I managed to do it without backing out this time. Having that done I took an anxious glance throughout the bus and spotted two people inside, besides me and the driver. The first one was a girl, supposedly about 17 years of age and she looked at me as if I was some kind of a freak or something.That made me decide to take a seat at the rear of the bus, where an old man was sitting, looking out of the window and not seeming to have noticed me at all. He looked kinda friendly, still very manly though, I noticed. He was sitting at the left end of the last row and I sat down at the right end."Only four stops ahead." I said to myself quietly. Though, not quietly enough, since now the old man seemed to have noticed me. Because it was dark outside I could spot him looking at me frequently through the window to my left, which, luckily, he did not seem to notice. By the way he looked at me I could imply that he was not as disgusted, as the girl in the front seemed to be about my appearance.When I got ready at home, after doing my make up, having chosen my nicest outfit and getting on my blonde wig, I have felt pretty self confident about my looks. I decided to wear a cute, blue summer dress with white points on it. Underneath I was wearing a pink thong and a bra of the same color. Also I was wearing a bracelet at both wrists and a cute, silver necklace. What really tops off my look, was my pink and shiny lip gloss, which made me look so girly, that I could almost fall in love with myself.The bus seemed to have stopped for a pretty long while now as I noticed that there has some kind of accident happened a few meters in front of us. "Perfect..." I thought. I started to notice the old men to my right trying to see what happened, but he could not see a thing because it was too dark outside and you could not see outside to well anyway because of the light inside the bus.I looked over to him and at the very same moment he looked back at me and smiled. I instantly turned my head to the left again and felt very uncomfortable and nervous. "Seems to be pretty serious over there." He said. I hesitated for a short moment, but since I am a pretty chatty person I answered: "Yeah. I guess I can say good bye to my plans for tonight." I even managed to sound not too manly, which I kinda was a bit proud of that moment. "Oh dear." He responded. "I wish I was your age again. Going out, meeting all those young people, having fun at the clubs. Drinking all night." He laughed. I smiled towards him and blushed a bit whilst doing so."So tell me." He continued. "I hope you don't mind me asking, but is this your first time going out dressed?"I was a bit shocked about his question, but at the same time I felt some kind of excitement because I kinda got the intention he could like guys like me. "It actually his." I responded and giggled a bit. "Well in that case let me tell you, you really look gorgeous, my dear."I blushed again. "Thank you very much, mister." I managed to put a smile on my face and he really seemed to like me see smile, at least I suggested he did, since he smiled back so friendly."So..." He continued speaking. "Would you mind me getting over there to chat a bit, since your evening plans are destroyed now and we both are stuck here?" I was getting very excited again and nodded shyly. When he got up and walked towards me I could spot a big bulge in his pants, but I pretended to not have seen it at all, even though it was pretty hard to overlook. He sat down on the seat right next to me so that his leg was pressed slightly against mine and I could feel the warmth of his body. He put his left arm behind me around the seat, just as he wanted to hold me like the guys do with their girlfriends at the movie theaters. At least I had this imagination at that moment. Now that he sat next to me my excitement reached a whole new level, having in mind that he is actually hard down there in his pants, smiling at me the whole time. I smiled back and tried to take a look outside to see if there was anything happening about the accident. Just at that moment a fire track passed by and the driver shouted: "This might take a while. I suggest you get out and take the subway or walk, guys." I looked at my seatmate and he suggested that we could take a walk together to the sub and I agreed. The bus driver opened the door and we got out. After we had left the scenery and entered an empty and quiet ally he said: "Oh, sorry for not having introduced me already, I am mister McDoden, but you can call me Alex, if you want." We stopped walking for a moment, I shook his hand and told him that my name was Fiona. "That is a wonderful name, did you choose it yourself?" I nodded and smiled at him. "So." He continued. "Since your party is over for tonight, I could offer to have some drinks at my place. It is right around the corner and I even have some bottles of wine in store, if you care for wine of course. I got that excitement again and actually started to feel very happy about how this evening was going so far and told him that it sounded lovely and I would love to have a glass of wine now to forget about the whole situation before. He smiled at me again and offered his arm for me to link with and we walked together to his lovely, little house. He opened the door and stepped aside. "Ladies first, of course." I smiled at him and walked inside, while he was checking out my backside and I hoped he liked it as much as all those guys on the internet, which I have shown myself so often during the last months.Having entered the house I noticed a very noticeable, but pleasant smell. The floor was covered with all the way, at least I suggested that from what I was able to see at that moment. Mr. McDoden asked me kindly to take a seat in the living room, while he entered the kitchen to get some glasses for us and a bottle of white wine. He placed everything on the glass table in the middle of the cozy living room, where I was sitting on the couch, smiling at him when he poured some whine into my glass. He sat down next to me and raised his glass. I did so too and we both took a good sip. "So, how do you like the whine, dear?" "I love it." I responded. "White whine is really my favorite, Mister McDoden." He filled up our glasses again. "I take it then you prefer to call me by my last name? Don't mind me asking, Fiona. If this is your think it is totally fine with me." "Well...." I started to respond quietly. "It really is kinda my thing. I can't really explain why exactly though....""And you don't have to. It is alright with me. No worries dear." He smiled and noticed that we already emptied the bottle. "I will get us another bottle, if you are up for it?""Oh yeah, totally." I responded and began giggling. While Mr. McDoden was at the kitchen, I noticed that I already had become a bit tipsy. I assumed that was because it was quite a while ago since I last ate something, but I was not really hungry at that point either so it was fine with me. Also it really helped with my nervousness and that was indeed a good thing. While entering the living room with two new bottles of that fine white whine Mr McDoden asked me if I would care for some music and I responded that it would be a wonderful idea. He arranged us some classic rock and roll and I kinda even liked it, even though I never really have been into that sort of music. As I started to move to the rhythm Mr McDoden smiled and me and asked: "I assume I made the right choice with that, haven't I ?""I admit, I really like it. It is quite encouraging indeed." I laughed.It did not take too long and we managed to empty the second bottle. Though you could actually say I did it mainly myself, since I always have been a fast drinker. If I haven't been that drunk already I would have probably noticed that Mr. McDoden really seemed to be very happy about my present state, but I guess that would have been alright with my anyway. What more could I have wished for anyway? Since the very beginning of the whole cross dressing thing I always was into older guys. Mr McDoden had a very manly body with a little belly and seemed to be pretty hairy allover. I always liked the imagination of being with a very well aged and masculine guy, to which compared with me, I really seemed very smooth and feminine. After all the experiences I had online with all those men I was even very easy and casual to get along and have nice conversations together.I don't know how and when exactly I got up and started to dance, but I felt really natural moving my hips to the music and being watched by Mr. McDoden, who had a very noticeable bulge in his pants again and did not seem to mind at all, and neither did I."My dear.." He started asking. "What would you think about a little...visual motivation?""I would love that!" I answered enthusiastically while I emptied another glass and had lots of fun dancing like a girl of the 50's.Mr. McDoden went over to his television and started a DVD. I instantly noticed that is was a video I have seen on xhamster already and told him that I really liked this one. "I knew you would like it Fiona. That girl really reminds me to you, I have to say." I loved that he referred to the cross dresser as girl and, of course, that he called me Fiona all the time. I really enjoyed my time with him and let him know how much I did so. "I am glad you enjoy our little private party, Fiona. I do you, too. Do you want another sip of that whine you like so well?" I nodded, danced along and let him fill up my glass again. He sat down on the couch again and started touching his bulge while he watched me dancing and sometimes noticing the video on the screen also. As I saw him doing it he asked me if I would mind him doing that and I responded that is was fine with me. Actually I came to realize that I was hard, too and I honestly had no clue for how long actually. But it kinda felt very exiting knowing that he probably had noticed that all the time. In that moment I really let go the last portion of nervousness and started to touch my clitty frequently. Sometimes I even looked at Mr. McDodens bulge while doing it. He smiled at me when he noticed that and I could not stop myself from giggling frivolously at that moment. "Fiona, why you don't come over here for a bit?" He asked. I stopped dancing, bite pointer while looking at him lasciviously and walked towards him. I stopped when I stood between his legs and he smiled at me. "Do you wanna get it out for daddy, Fiona?" I giggled like a little girl, bend down and unzipped his pants. I helped him undress his pants and got on my knees and started caressing his bulge through his underwear softly.He closed his eyes and exhaled slowly while I did so. At that moment I decided to be brave. I grabbed under his shorts and took out his cock a bit. Mr McDoden opened his eyes again to see what I would do now. I looked up at him, smiled, took my tongue out and started to suck the head of his cock, after I pulled his forehead back. "Oh my...." He said and leaned back, looking at the wall, smiling.So I finally managed to reach my goal. Dressed, made up, drunken and horny. Together with a sexy daddy who really appreciates my sissy me. Could this be heaven? Damn, this could be hell and I would enjoy it anyway. What else would happen tonight? I was totally up to find it out and let go. I love this.