A Later In Life Prom Fantasy free porn video

A Later in Life Prom Fantasy By Delanna Madison It must have been the 5th or 6th time that I checked my makeup and worked at getting my hair just perfect. It seemed as though I would never truly be satisfied with the results. "Come on Del, you're acting like a silly schoolgirl on her first date," I thought to myself. Then the irony struck me and I had to laugh. In a way, that's exactly what I was. Not quite a schoolgirl in terms of age, but soon to be on my way to my first prom, if not my first date. Let me tell you a bit about myself. I started crossdressing from a very early age. My first recollection of sneaking into the basement one Saturday morning at the age of 6 or 7 to try on my sister's dance costumes is still very vivid in my mind. Over the years I tried to deny my feminine orientation, without much success. I carried a great deal of guilt with me along the way. Then several years ago I discovered an amazing thing. The internet! I found a whole community of people quite like myself. I slowly began to accept the fact that the femme part of my personality was what made me who I am. I no longer felt ashamed of my desire to dress. More importantly, I finally mustered the courage to go out in public as a woman. There was no turning back after that! While I do not live full time as a woman, I find that I dress and feel the part more often now than ever before. It hasn't been quite a year since that fateful first step, and I have made some dear friends as a result. And that's what brings me to awaiting the arrival of my date and attending my first prom. It's hard to believe that not that long ago my good friend Stephanie had introduced me to Jay. Jay was genuinely pleasant to be around. Quite accepting of the T-girls in the club we met at, without being vulgar or lecherous in the manner that many other "admirers" I had the ill fortune of meeting always seemed to be. Being that I only started going out enfemme recently, his easy going manner took a lot of the edge off. He was quite understanding and supportive. I found that although I was never really attracted to men, whenever he met up with us I would subtly vie for his attention. Soon it seemed like it wasn't all that necessary, as he would connect with me as soon as he saw me. And yet during that time, he never once said anything that would be considered as "making a pass" at me. I knew he enjoyed my company, but I couldn't tell if there was anything else there. What I did know is the more I saw him, the more attracted I was to him. A very strange feeling for me, and one that I was having a bit of a hard time adjusting to. I even found myself taking more time than usual trying to look good on nights when I knew I would run into him. One night we were talking about our high school days. He confided in me that his prom was a complete wash out as the girl he invited ended up going home with someone else. I felt awful for him. What a terrible ego crush for anyone to go through. I admitted to him that I had never gone to any of our proms. I was quite the rebellious type and the idea of getting into a tux and hanging out with all the "jock types" was totally against my grain. "Besides," I said, "I would much rather have gone in a killer prom gown anyway." We both had a good laugh at that. "I'm sure you would have looked great," he said. "You know, it's never too late. Why don't we make up for a lost opportunity?" Not quite sure what he was referring to I asked what he meant. He told me that the local transgender support group was having an alternative adult prom in a few weeks. I thought about it for a minute and decided that it sounded like it might be fun. "Of course no one has asked me yet and I would hate to go all by my lonesome," I kidded with him. He took my hand in his and asked me if I would like to go to the prom with him. I couldn't believe what hearing those words felt like. I must have blushed about 4 shades of red and Jay obviously noticed. He seemed flustered and quickly apologized for embarrassing me. He tried to pull his hand back but I held it tight and told him that I wasn't embarrassed at all and that I would love to go to the prom with him. "I'll go on one condition. You have to promise me that you'll be on your best behavior," I stated. I think his cheeks were now as fully red as mine had been just a few moments before. I gave him a wink and reassured him that I was teasing him and it really did sound like it would be a fun evening. The date was on. Stephanie, who was sitting in the next booth over, turned around and said that she couldn't help but overhearing us. "Del, Paul and I are going too. It should be a great time. And, it will give you and me a chance to get out to do some power shopping before the big night!" "Now you're talking girlfriend," I said. "You know I'll never turn down the chance to raid the local mall!" As Jay walked me out to my car I thought about the evening. Accepting my first date, going to a prom in a way I had only fantasized about, and having an excuse to go shopping with my best friend. All in all, not a bad night! "Thanks for accepting my invitation," he said. "I was thinking that you might not." "Well it does seem a little strange," I admitted. "But I feel very comfortable with you. You can be quite the gentleman. If that wasn't the case, I can assure you that you would never have gotten the chance to ask." "That's me, gentleman Jay," he joked. With that he leaned in and gave me a kiss on the cheek. "I wouldn't want to ruin your impression of me." "Well now, you are full of surprises tonight," I said. "That was sweet!" I got in my car and Jay walked off to his. I sat there for a moment, thinking. While a kiss on the cheek is about as tame as you can get, I found myself totally flushed. There was no doubt in my mind that I was really attracted to Jay. "Wow girl, he would need to be picking you up off the pavement if kissed you on the lips," I thought to myself. I couldn't help laughing at that thought as I started my car of drove off. During the next week I had many opportunities to think about the upcoming event. It also gave me pause to think about Jay and the attraction that I felt towards him. It was a bit disconcerting. I had never had any interest in men before. Although I had entertained the occasional fantasy while being dressed enfemme. I tried hard to figure out why I felt this way. Maybe it was the progress I had made in integrating the female aspect of my personality. Perhaps it was the way that Jay always treated me as a female and always with respect. Maybe it was just a phase. Maybe if I didn't stop trying so hard to analyze my feelings I would make myself crazy! I decided to push the mental inquisition into a recess of my mind and just try to enjoy my first date as best I could. I woke up early on the Saturday before the prom. Stephanie and I were planning on picking out our dresses, then hitting the mall for whatever else we might need. I went out for my morning walk as usual. I decided that an additional mile or two might be in order. 'No sense in letting an extra pound or two creep up on me,' I thought to myself. I took a quick shower, put on my makeup, and put my hair into a pony tail. Knowing that I would be trying on dresses for the better part of the morning, I decided to make it as easy on myself as I could. After slipping into a black bra and panties, I put on a pair of black capris and a print tunic top. Then digging around in my closet, I found the most comfortable black strappy sandals I owned. A quick look in the mirror, a dab of perfume and I was ready to go just as I heard Steph beeping her car horn in front of my place. "Hey girl, you look like you are going out shopping for men, not dresses," she kidded. "Not a chance Steph," as I batted my eyelids furiously at her. "Why you little tart! It looks like I'm going to need to keep a close eye on you," she joked. As we pulled away she asked, "Seriously. Are you starting to find yourself attracted to men now too?" I didn't have to think about that to hard since I had been asking myself the same question all week. "I can't really say that I am. Although I do find myself appreciating the looks of a handsome man, where I never really did before. Or at least I would never admit that to myself." "Does Jay fall into that category?" she asked. I knew the questions about my feelings for Jay would pop up sooner or later. At least we could get them out of the way early. "I do think Jay is handsome and I know that I enjoy being around him. Beyond that it's too early to tell. Frankly I don't know if I could think of him as anything more than a friend. I'm just now getting comfortable being out in the world as Delanna. I think anything more than that would too complicated. So let's agree that I like him as a friend and leave it at that. OK?" If there's one thing I love about Steph, she knows me well enough to know when it's time to change the subject. "I understand dear. Just know that I am always here for you if you need or want to talk about Jay or anything else," she said. "So how about a quick stop at Starbucks before we start." "Woo Hoo.....caffeine time. Drive on girl, drive on." Our first stop was at a shop that caters to crossdressers. I had been in the shop a few times and had always enjoyed being treated so well. Jillian was at the counter and waved us over when we came in the door. "Hi dears! Are you two looking for anything special or just a general search and destroy mission," she kidded. We told her that we were going to the alternative prom next weekend and needed to find the perfect dresses. "Wonderful," she said, "I brought in some additional inventory just for the occasion. Quite a few of the girls stopped in to buy their party finery already. Now let's go to work finding you two the look that will stop traffic!" "I can already stop traffic," I quipped, "now can you find something that will make me look nice?" "Don't mind her," Steph added, "she always gets insecure when she's had too much coffee." We all giggled and went off to the racks. Jillian picked out several dresses for each of us to try on. We hit the dressing rooms with abandon. We would try on a dress and then go out front to gather each others opinions. Steph started out with a deep burgundy strapless gown and I a cute pink taffeta number with lots of sway and the most adorable pouffy sleeves. If there's one thing I really like about Jillian it's her complete honesty. She told Steph that while her dress was very flattering, the burgundy color wasn't quite right for her hair color. "As for you Del, while I don't miss the mark too often I'm afraid that I did with that one," she offered. "If it was shorter with a frilly petticoat underneath, the only thing that would be missing would be a pair of Mary Janes and a lollypop. Not quite the look for an elegant night out." That mental picture was all it took for me to beat a hasty retreat to the dressing room. This went on for almost two hours and I loved every single second of it. I never tire of trying on different things! In the end we all decided the Steph looked absolutely killer in a red floor length silk gown with tiny spaghetti straps. It was quite form fitting and she looked great in it. For me, I chose a blue halter gown that was a corset design in the bust leading down to a very full chiffon skirt. There was a darling matching chiffon drape shawl to go along with it. After Jillian helped lace up the ties in the back and I took my first step out of the dressing room, I knew I had "the one!" "This is the most feminine feeling dress I think I have ever worn," I bubbled. I threw my arms around Jillian. "You're the best girl!" After ringing up our new found treasures we said our goodbyes and headed for the mall to grab the few things we would need to complete our looks. It's amazing how a few things could take the better part of the day, but we had a great time. After picking up shoes to match our dresses, earrings and necklaces, purses, and a few essentials like nylons and such, we were ready to call it a day. "Well Steph, it looks like we accomplished our mission for the day," I said. "If our dates don't like the way we look, it's their loss!" We hugged and said our goodbyes. All during the week preceding the prom, I couldn't help but think about it. A serious bit of anxiety was setting in. So many thoughts kept running through my head. I knew I wouldn't be the oldest girl there, but certainly close enough. How would I possibly compare against all those younger and more attractive girls? And what about Jay? Would he find me attractive? Could I keep his attention and interest for the evening? What if he tried to make a pass at me? Would I want him to? What if he didn't? I was on the verge of making myself crazy. I called Steph several times during the week to use her as my sounding board. She was a dear. Always listening to me patiently and letting me vent my thoughts and feelings. She would occasionally venture her opinion, but mostly she just let me ramble on. Then she gave me a bit of wisdom that was so obvious, but one that I couldn't seem to find on my own. "Del," she advised, "it's really this simple. Forget about comparing yourself to anyone else. You will know quite a few of us there anyway. Don't worry about the what ifs. Just be yourself and have some fun. And as far as Jay is concerned, whatever happens or doesn't happen, your heart will not steer you wrong!" The day finally arrived and I was trying my best not to be nervous. I plucked and shaved for what seemed like hours. A fresh coat of nail polish was in order and I hoped that might take my mind off things. After painting my finger and toe nails, my nerves were no better off. I decided that what I really needed was a nice warm bath, a little classical music, and a small glass of wine to settle myself down. I laid evening gown on the bed and headed for the relaxation of bubble land! That definitely did the trick. I sat down at the vanity and took my time getting my makeup just right. I put my hair up and secured it in place with a pretty set of combs that matched my hair color almost perfectly, allowing a few whisps to frame my face. I placed the long dangling earrings into my pierced ears and clasped the matching necklace around my neck. Daubing on a little of my favorite Gucci perfume and I was ready to start getting dressed. I slipped into a pair of light blue satin panties and tucked away the "bits". I eased the lace top thigh high nylons up my smooth legs. I struggled a bit getting into my gown as the laces were already tied in the back, but eventually I was able to wriggle into it. Sliding the breast forms under the dress was a bit of a challenge, but the end result was worth the effort. The same wave of femininity swept over me as it did in the store. 'I'll never tire of this feeling,' I thought to myself. The new light blue heels I bought for the occasion fit perfectly. I was so glad for that because I knew by the end of the night I would be ready to sacrifice them to appease the foot gods! I threw a few essentials into my beaded clutch and took one more look in the mirror. "Really girl.....enough! You are either seriously insecure or seriously vain," I mused to myself. Realizing that Jay should be over any minute I went into the kitchen and was about to pour myself another glass of wine when I thought better of the idea. Just then the door bell rang. I didn't think it was possible but my nerves stepped up yet another notch. My hand actually trembled a bit as I reached for the door and opened it. For a moment I couldn't believe I was looking at Jay. He was the picture of handsome standing there in his black tux. There was a moment or two of awkward silence when he broke the ice and said, "It's a little too late to find a different tux if you don't like this one!" Realizing that I had been standing there staring at him I smiled and invited him in. "I think the one you have on will do just fine," I said. As I closed the door I couldn't keep from teasing him a little." Well you really clean up nicely Jay. Quite a departure from your normal jeans and hiking boots. Now tell the truth, did you do this all yourself or did you have help?" He quipped that, believe it or not, he actually didn't need any help getting ready for tonight. "I was a little bummed out that the formal wear place was all out of blue jean tuxedos. I even had the red Converse tennis shoes picked out in advance." We broke out laughing. Just what we both needed to calm our nerves .Then he took my hands into his and said, "You always look nice when we have gotten together, but tonight.... well you look absolutely beautiful." I felt my cheeks flush. "Thank you Jay. That is so sweet of you to say." Then as he looked me over he remarked, "There is just something missing. I can't quite put my finger on it." I was somewhat taken aback. Then he released my hands and told me he would be right back as he turned and walked out of the apartment. What in the world was this all about? When he returned a few moments later he was holding a small box with a pretty lavender bow. He opened the box and took out a beautiful corsage that he slipped onto my wrist. "Now your look is complete. You'll be the prettiest girl at the prom." I leaned into him and gave him a light kiss on the cheek. "Handsome and thoughtful. You'll be quite a catch for some lucky girl one day." He replied, "I do have one special girl in mind, but I don't think she realizes it yet." "Well you had better not mention her again. This is to be our night, remember." I teased. It was hard to tell if there was the beginning of a spark there, or if I was just caught up in the moment. In any case, I got the feeling that this was going to be a wonderful evening after all. I grabbed my purse off the table and the sheer shawl from the chair. He took it from me and draped it across my shoulders. As we walked down the driveway to his car he all but raced in front of me to get to the passenger side first so he could open the door for me. "Be careful Jay, I could really get used to this kind of attention," I quipped. The drive to the ballroom was thankfully short as my nervousness was starting to kick into high gear all over again. Looking over at Jay I could tell he was a little anxious as well. Then we arrived. Jay handed the valet the keys and as he drove off Jay took my arm in his. "Well, it's now or never to make our grand appearance," he said. I smiled at him and followed his lead into the ballroom. The room was already pretty full when we walked in. There were quite a few girls there from the club and from the local support group. We walked over and said hello. Jay moved over to talk to several of his friends while we girls chatted and giggled about picking out our dresses, our dates for the night, our shoes and makeup. My nerves were finally calm and I felt very comfortable for the first time all day. Just then I felt Jay put his arm around my waist and ask if I wanted to get a drink. I told the girls we would catch up with them at dinner and made our way to the bar. "Should we keep with tradition and start out with a glass of punch?" he asked. I agreed and he poured us both a glass. After one sip I knew this wasn't at all like what they would have had at my high school prom. "Whoa," I said, "I think they added some red food color to Long Island Iced Tea. This is all alcohol! Tasty, but not too many for this girl." "Don't worry, my intention is not to get you drunk and take advantage of you," he said with the most serious look on his face. "Oh really," I replied raising an eyebrow. "I wasn't aware that you had any intentions. Are there some ulterior motives at work here I should know about?" As hard as I tried to keep a straight face, his cheeks flushed with color so quickly that I couldn't hold back a laugh. "I'm sorry Jay, but I can be a bit of a tease at times. Especially when I know I can get such a quick reaction. I promise I'll be good. I really don't mean to embarrass you." "No problem. I guess I'm still trying to get a feel for when you are serious or when you're kidding with me," he replied. We chatted with our friends over dinner. The conversation ranged from local news and events to politics to the latest who's going out with whom. The food was good and the conversation and company was even better. I was so glad I had accepted Jay's invitation. At one point during dinner I felt a slight nudge under the table. My friend Steph looked over at me, tilted her head in Jay's direction and winked. I gave my head the slightest shake no, trying to convey that nothing was going on between us. She just smiled and winked again. After dinner we sat and chatted a bit more. As it turned out, it was the first prom for a few of the other girls at the table too. We raised our glasses and toasted to the "better late than never" crowd. Soon the lights dimmed and the band came on stage. I'm not sure what I was expecting, but the band turned out to be a 50's Big Band style. Not exactly my favorite choice of music, but what the heck. After a moment of tuning up they started out with a really swinging number. Jay took my hand and said, "I think it's time to trip the light fantastic." "Jay, I should have told you this before, but it never crossed my mind. I have a lingering knee injury since a skiing accident several years ago. If I get up and try to dance to this, I can all but guarantee you that you will be carrying me out." I could see by the look in his eyes that he was trying to tell if I was serious or if I just didn't want to dance with him. I reassured him, "Jay really, it's not that I don't want to dance with you. I'd love to. But all it takes is one wrong move and I'll be out of commission for days. What if I promise you all the slow dances tonight?" I think he realized then that I wasn't putting him off and told me he expected me to keep my promise. "Cross my heart. But I would understand if you wanted to dance with one of the other girls when a lively song comes around," I said with a little pout. "You're not going to get rid of me that easily," he chided. It didn't take too long for the first slow song to find its way into the play list. Jay took my hand again and said, "I do believe someone made me a promise." "And I'm the kind of girl who always keeps her promises," I replied. He led me onto the dance floor. As he slipped his hands around my waist and I draped mine over his shoulders, I felt a rush shoot all the way through me. 'Get a grip girl!' I thought to myself. But it was there, undeniable. Maybe it was the mood of the night, or the completely feminine way I felt. But something was definitely happening. I looked into his eyes for a few moments, and then laid my head on his shoulder, letting the music and the motions carry me away. 'So this is what romance is supposed to feel like,' I thought. And so it went for every slow song the band played. In between we sat and chatted with each other or with some of the couples that had come close to dancing themselves out for the count. Towards the end of the evening while we were floating across the dance floor to yet another slow and romantic song, Jay felt a tap on his shoulder. Steve, who we knew from the bar, was asking if he could cut in for a dance. Jay politely stepped away and I could see him heading towards our table as Steve took me in his arms. Now, I didn't know him all that well, but we had run into each other a few times. Never much more than a passing hello was ever exchanged between us. I could tell that he was on his way to having a bit too much to drink. I could also tell that things were about to go bad when he leaned into me hard and said, "Wouldn't you rather spend the rest of the night with me than that dweeb you're with." While getting attention is always nice, this kind of attention I could do without. I firmly pushed him back from me and told him that Jay was a very sweet guy and I was totally happy being here with him. Then he slid his hands from my waist and grabbed my ass tightly with both hands. He leaned in hard again and said, "C'mon baby. I know what kind of a man you really want." Trying my best not to make a scene, I grabbed his wrists and pulled his hands off of me completely. A line from the movie The Crying Game came to me as I patted down the lapels on his jacket. "Have you ever tried to pick up your teeth with a broken arm?" I asked. "Well if you ever touch me again you are going to find out just how hard that is to do." I think he was stunned a little as I turned to leave the dance floor. I barely heard him utter, "Your loss baby, not mine," as I walked away. That's when I saw Jay sitting at the table. He had seen everything and the crushed look in his eyes almost brought me to tears. I went over to him and tried to apologize. He got up and told me that he needed to get some fresh air. I looked after him as he headed out onto the balcony. I started to get up to join him, but I decided I needed a minute to compose myself as well. When I went onto the balcony Jay was leaning on the railing looking out over the city. I walked up slowly and put my hand on his shoulder. "Jay, I am sooo sorry about what happened in there." He turned towards me and told me I had nothing to apologize for. He knew it wasn't my fault. "Steve can be a bit of an ass when he's been drinking," he said. "But there, for just a minute I was back at my high school prom watching my date laughing and smiling as she walked out the door with another guy. I could see that wasn't happening in this case, but I guess the memory kind of numbed me. I should have gone right over and come to your rescue. I should be the one apologizing to you." We stood there for a moment looking at each other. I moved in closer and put my arms around him. "I thought that's what you might have been feeling. I could see the hurt in your eyes." "Well it's over with and I think can let the past rest," he sighed. Looking into his deep green eyes I told him that I would be a fool to even think about being here with anyone but him. "Jay, this has been such a wonderful night. Finally getting to go to my prom as the person I really am. And you have been the best date a girl could have. You've been sweet, considerate, and polite. Of course being handsome as heck is the icing on the cake as far as I'm concerned. I really can't remember the last time that I have been so happy and had such a great time. So let's not allow 4 minutes of dealing with a drunken jerk ruin that." He agreed. "OK. We won't let that spoil our night. But you were kidding about the handsome part right?" I gave him a playful swat on the arm. "Learn to take a compliment, will you!" With that I leaned in close and kissed him. Our lips lingered for a moment and I felt the same rush go down my spine as when he first took me onto the dance floor. "Shall we go back inside? I think I hear another slow song," I said. He looked at me for a moment then winked, "Only if you promise I can have another one of those before the evening is over." "Why wait," I winked back and kissed him again. A longer and very tender kiss. We made our way back inside just in time to see Steve sprawling on the floor. Some guy was standing over him shouting "If you ever touch her like that again you won't be getting up." Jay and I looked at each other and broke out laughing. "Looks like Steve grabbed the wrong girls' ass," I snorted. I took Jays arm and whispered, "I think I can find a CD or two with a few songs we can dance to back at my place. Why don't we call it a night here and have a glass of wine and dance in a little more over there? After all, I am not about to have you leave another prom without your date." We looked for our friends to say our goodnights. Stephanie came over and hugged me. "I knew there was a spark there," she whispered. I brushed it off and assured her there was nothing going on. "Yeah, right," she laughed. The drive back to my apartment was quite lovely. The sky was clear and the moon was a brilliant floating globe. I contemplated the evening and the wonderful time I had with Jay. I knew that I had reached something of a turning point personally as well. I knew that I wanted to dance in his arms again tonight. And that I would be sharing something more than a kiss with him. Yes, much more than a kiss. We pulled into a space next to my car. Jay shot me a look as I started to open the door. I took the cue and waited for him to come around to the passenger side and open the door for me. We slowly walked up the drive arm in arm. As I turned they key in the lock, Jay put his hand on my shoulder. "Are you really sure you're comfortable inviting me in?" he asked. I turned to face him. "Yes Jay, I am totally comfortable. I have had such an awesome night, and I have you to thank for that. You just need to make me a promise now." "And what promise is that?" he asked. "You need to promise me that you will be on your best behavior," I said. "Del, I promise you I'll behave like a gentleman." I had no doubt that he meant what he said. I wrapped my arms around his neck and kissed him tenderly. With a twinkle in my eye I replied, "Jay if there is one thing you should never do, it's to make a promise that I have no intention of letting you keep!!!" THE END