Crossdresser Convention

I am getting ready to attend another crossdressing convention, trying to place my things into just a couple of suitcases. It is not an easy task at all, putting my panties, bra's, slips, nylon stockings, my makeup, my wig stands, plus several different wigs to wear, let alone several pairs of high heels. Besides this I have several hanging bags to put my dresses, skirts and blouses, and night gowns into to last me for the five wonderful days that I can become the lady I really want to be.

My heart is pounding with excitement during all this packing and putting things into my truck, I always love this time off from the work I do, it's rather hard to dress up feminine and go to work although I have worn girls levis, and feminine tops to work I never heard anyone say anything so that's was good.

Once I get on the road to the particular hotel that is holding the convention I calm down somewhat, but then when I arrive and have to go check in, I have to let the desk know I am here for that particular convention to get the discount rate. So far in the 10 different conventions I have attended the desk persons have all been very receptive, no smirks, or comments have been heard or seen.

Once in my room I hang the dresses, skirts and blouses and the nightgowns up and check to see that everything is good to wear. Unpack the suitcases and get the wig stands out so I can prepare them to wear. Once I have things laid out the way I want them I begin the process of shaving close, then a nice warm shower to relax from the trip.

Once I am done with that, I put on panties and bra, with my silicon breast forms, (I have two different sizes a b cup, and a c cup) the pair I choose to wear depends on what I am going to wear as different materials in the dress or blouse will show different. I am not looking to be big in the breast area like some of the others here, I just want a nice feminine look. I sit in my panties and bra to paint my nails, usually a nice red or pink, depending on what I am wearing. It takes me a bit to do this but I think it helps in the overall look that I want to show. I dress in a classic style like what a woman would wear to work at an office. Tonight (Wednesday) is a meet and greet event, not a dress up deal at all. But there is always the possibility that I can maybe meet a man in the bar, seems that a lot of men like to also follow these conventions and I know I look forward to meeting them.

I finally am done with my nails and they are dry so I can dress without smearing the polish, I decide to wear a Kathy Ireland skirt and blouse outfit, and I know I am no way as pretty as she is, but I sure like to feel I am a little bit prettier than I am as a male. I have already put on my thigh high nylons, I pull the grey pleated skirt up and fasten the button and zipper, over the half slip I just put on first, then a camisole on top and the white sleeveless blouse, the skirt is soft as is the blouse, I dearly love to wear this outfit, I feel younger but alas I need more years than the outfit can do. I pull on the page boy wig in a dark auburn color that is just shoulder length in back and sides, it has bangs that just hit midway on my forehead. Prior to dressing I had put on my makeup so as not to smear that on my blouse or skirt, now I just need to touch up my lips with a pale pink lip stick and I am ready to go downstairs to see who I have already met or may know from the internet, or the other conventions I have attended.

By 8:00 PM I am ready for the bar, the meeting is ok but I did not know very many this year, not like some years when I see several friends or acquaintances. I walk to the bar area and go inside, takes a few minutes to let my glasses adjust to the low light, I walk to the bar and order a frozen daiquiri, when I had it in hand I asked the bartender to make a tab if he could for my room, not a problem honey he said and I felt so good. I went to a table next to the wall with a good view of the whole room, I had not been there long when I noticed two guys at the farther end of the bar checking me out. Darn wish I had a friend here with me. I had no more than thought that when Laura whom I had met a bit earlier came in looking around, she spotted me and came over and asked if she could join with me. Sure Laura please do, we can get more acquainted. A waitress came over and asked Laura if she would like a drink and she said yes I will have whatever Deborah is having. I told the waitress to put it on my tab.

When she came back with the drink, the waitress said the two at the bar wanted to pay for the drinks, but I told her no I have already done that. Laura and I giggled a bit over that, but I said maybe later if they would like. The waitress went right to them and we could see them nod their heads like they understood. Laura and I started to chat a bit, I told her about my back ground and she told me hers, we seem to be getting along very well. I asked her if she had ever been with a man before, as the two at the bar was watching us quite a lot. She laughed and said yes she had been with a man before and was looking to hook up. Was I she asked? I said yes unless she just wanted to go to my room and we could just do each other. Laura really laughed now and said she sure wouldn't mind that, but she was looking to do a bit more. I laughed right then also and told her I was also looking for more than that.

We were both just about done with our drinks when the waitress came over with two more from the gentlemen at the bar. We both picked the drinks up and turned to them and gave a sign that said thanks. They both got up and came over, one to each side of the booth, they asked if they could join us and we both nodded that yes they could. James sat next to me and Craig next to Laura. They both asked if we were with the convention and we both said yes, James said he wasn't sure as we were both so pretty. I gave him a slap on the shoulder and said you are just saying that. He laughed and said ok, but it's the truth and he should know as they both follow the conventions because they like what they can get. I said oh really, are you saying you want something? Craig spoke up and said they both wanted the same thing we want a nice evening with maybe some play time if we would like that.

I spoke to Laura and said we need to powder our noses, she agreed and we moved to get up when James said they would just wait there for us, I told him it might be a bit as we can not use the ladies room here, we have to go to our rooms, he said that's ok they would wait. Laura and I headed for the elevator and went inside she asked where my room was, I told her, her rooms were further up and she did not think it was big enough to have a foursome in. I said check my room first and see what you think. When we got there she was surprised because it was more a suite than just a room, I explained it helps to have perks. There was one big king sized bed in the main bedroom, in the living or second bedroom it was just a regular double bed. She said wow we could both be busy and not be in the same room. She went to the bathroom and screamed we could have a party here in the Jacuzzi if we so liked to do that. When she was finished I went in and used the commode and when done, I asked her if she really wanted to go pick up James and Craig, she said yes but she was worried about what could happen, I told her we could go back to the bar and talk and see if things were ok.

I told her I was also worried but more about sexually transmitted dieses than anything else, as I did not think they would try something really stupid at this hotel. So we both went back to the bar. James and Craig was still at the table and as we came in Craig gave a nod to the waitress and as we sat down she delivered new drinks for us. We chatted some more and we both expressed our concerns to them, and they also said they were worried also and about the same things. We talked some more and ended up having one more drink. By this time it was getting on to 10 PM so if we were going to do anything we best get at it.

We all got up and headed for my room, on the way up in the elevator Craig and Laura were in a clinch, James looked at me and had such a face that I asked him if he would like the same, he did not say a word just took me in his arms and kissed me. We got to the room and went inside, Laura and Craig were getting to the business at hand by hugging and kissing each other, James and I went into the master bed room and closed the door. James asked me if I would be ok if we just mutually jacked each other off, I said ok, but is that all he wanted to do? He said no but he wanted to come back each evening for more if I would be comfortable with that. I said ok. James asked me to sit on the edge of the bed which I did, he stood in front of me for a short time then asked me to open his pants, I immediately reached up and pulled his belt open releasing the buckle, his pants had the little silver catch that slides into place so I opened that and pulled his zipper down, all the while noticing that he had a nice bulge inside.

When his pants dropped I was happy to see panties and not man shorts, they were wet with pre cum so I pulled them down and his beautiful black cock was there, all of 8 plus inches and larger around than mine, I grasped his cock with my hands and started to slowly jack him, James said Deborah your hands are so soft and warm it feels so very good. I continued to jack him and he got harder and a bit bigger, then he said I am so close you better get a towel. I laughed and said your closer than I am and besides I am sitting, I let him go long enough for him to get a towel, when I grasped his cock again he let out a groan and said jack me good now I need to cum. I used both hands to hold his cock and jack faster and faster he groaned loudly and started to cum, the first ejaculation was enormous and had I not had the towel right there it would have shot all over my blouse. He had four big pulses of cum shoot out, then it just dripped out of the end for a bit. James said it was wonderful to have someone else jack him off as it feels so much better. He bent down and pulled his panties (which were pink by the way) back up and his pants followed, once he had them zipped and buckled he said now it's my turn.

James helped me stand up and he gave me a big hug and a kiss, then turned me around so now he was sitting on the bed, he started his hands up my legs from the lower calf one hand on each leg, he slowly moved them up my nylons saying my legs were nice and smooth, he loved the feel of the material. As his hands and wrists came into contact with my skirt and half slip, he let the material slide down his arms as he slowly dropped down from the bed to be on his knees, as his hands continued up my legs he moved them to the backs of my legs and he slowly caressed my butt, it felt so good to be caressed this way. He then moved his hands to the front and slowly took my panty covered cock in his hands, my panties were also very wet with pre cum, and he said he would love to suck my panties just to taste it, but he would wait until the next time we were together. He put his fingers into the top of my panties and slowly pulled them down, and out of the way, my cock was finally out and now he could see that I had 7 inches and it was a bit smaller than his in size around. He slowly started to jack me off, and I said in a quiet voice that it was feeling so good. It did not take very long and I ejaculated more than I usually do, but in quantity it was not much compared to what he had shot into the towel. As I started to go soft, he let go and pulled my panties up and slowly stood. Again he put his arms around me hugging me and then kissing me, I was not so much into the kissing but with James it felt so good.

James said I think it's time to say good night but only if you promise that we can meet up again tomorrow, I told James I would love to meet with him again tomorrow night. But with the condition that we do more than we did tonight, James said he would love to do more, but like we both have said we do not want to get STD's. I told him I am very sure I have none, and James said the same, he asked me if I liked to suck cock and I said for sure I do, he said that's good I love to be sucked. He then asked if I was ok if he sucked mine, I said sure if he liked to do it, I would let him.

I am sort of a funny type of person I love to bring pleasure to my partner as I get great pleasure from doing that. I have even ejaculated without anyone touching me while I am sucking a cock, or a pussy. James said till tomorrow then? Ok, we opened the door to the kitchen part of the suite and we could hear Laura and Craig in the other room still going at it. James left then and I went back to the bedroom and closed the doors and started taking my things off getting ready for bed.

Not much later I heard Laura and Craig in the kitchen, Laura peeked in the bedroom and said she would see me tomorrow at breakfast. She closed the door and I finished getting ready for bed, put my nightgown on turned the lights off and went to sleep and slept real sound until the alarm went off at 6:30 AM, a girl needs time to get things right before stepping out the door.