Reflection 2 - You'll Always Remember Your First free porn video

Reflection 2 - You'll always remember your first By Jena Corso Edited By Angela Meyers So with my 200th story as I promised I'm writing about men and my first date. You love them. You hate them. You are one or for some were one. Even though you think you know things from a male perspective, once you get close to a kiss or a hook up or a date.... Only thing I can I tell you for sure is you never do know what you think you know! That's for sure. So I love all my fans and thank you so so so so much from the bottom of my heart for reading my stories, emailing me, commenting and for some getting to know me. I hope to meet more of you once this virus shit is behind us. Please write me at [email protected] anytime, and hopefully I'll hear from a lot of you and we can chat or trade stories or for girls that need advice. I'm there for you like so many have been for me over the years!! So guys? Dating???? Well is there ever a date or even a kiss where you are kicking yourself in the ass a little for wanting it or agreeing to it, yet you are still excited about showing up for? Then you can relate because that's exactly how it started for me in so many ways. Yes I'm a slow starter, and took longer than I should have or wanted or who the hell knows. It's confidence. It's guilt. It's lack of conviction for a long time to who I am or what i want to be. It's all that and ultimately just the constant questioning of one's soul about whether this is what I'm really supposed to be doing? Better described as how you're made up inside before you even put a drop of make up on the outside. So even if you've mastered the cosmetic side of things and you're in your favorite outfit having a good hair day, if your date doesn't scare you to death, then trust me you're drunk beyond belief or dead. And I've been drunk, but never that drunk. So in the TG dictionary in the "please pray I look pretty enough section," there a word that combines fear, excitement, a hope of acceptance and indescribable anxiety. That word is dating. And more specifically dating a cute guy for the first time while you're in a dress. Never does it start like you hoped it would? Maybe like on tv? Or how you fantasized about? Like a romance novel? - Nah, that would be too girly right? But wait? I am the girl now. The girl on the date with a guy that maybe, hopefully likes me? And for at least some of the right reasons? Well if so, then that's exciting and terrifying and like holy shit is it finally actually happening? Basically that's what you say to yourself. Well yeah I think it is, and that's if he shows or I don't piss my panties before I get there. As a boy I've always jumped into things with so much less thought and been daring, but once I put on a skirt somehow all that changed. Slowly dipping in one toe and overthinking, you realize it is not just about getting clocked, but was more about being accepted. Accepted in a skin you feel most comfortable in and in one you've hated that hair grows out of in all the wrong places. A soft sensitive skin that was probably who you were always meant to be, and all you want to do is hope that's how you'll be accepted. So date night! Cute guys! And you so hope you are. Looking cute that is! So before I even describe it, my first date was not my first boy. More explicitly, not my first kiss. No, I wasn't a slut! (Even if in some of my own fantasies I might have dreamed I could be)! There is the alcohol and peer pressure, but really I can blame neither. It just happened. Did I want it to happen? Yeah! Did I want it to happen like it did? Not exactly, but I didn't stop it. That part I do blame a little on the vodka and a few friends. I was in my late twenties and it was the nineties during a period where I had been dressing for a few years on and off since I first tried it on Halloween. My relationship with my girlfriend had ended, but we were still friends and we still talked about so much. (Even this!) I always thought back then we were going to get married and this was just something sexual or just for fun, or as she said an expression of another side of myself, but I know now over two decades later it was all that and so much more. In the beginning of my solo dressing after our relationship, I'd dress and mostly go for walks. Just walks in Manhattan, especially through Greenwich Village and at times take a ride in my car to the suburbs. A club here and there I knew was safe and had other CD/TVs, and I did make a few new friends. It felt nice just to get out and was like a relief from my male life. Being dressed. Feeling pretty and not being - Me? As time went on, I got more brazen but was never that comfortable alone. Dating other girls was ok, but just didn't last. Was it me or them? Both is the ,and the few I told about my hobby/stress reliever were not into it. Some of my newer friends were wonderful and taught me a lot, but I'm trying to be kind saying they're a bit more advanced than me, and I wasn't ready to go there. Some were around my age and some much older, but that was not an issue. Back then I was NYC street smart but they were Trans street smart, and I was a chicken about a lot of things. Chicken about taking next steps I was egged on to take, and that meant sex (gay or bi or whatever), some drug use (which I would not go near) and I was always fearful even if I did cave to some peer pressure about what this would make me? I was also still stuck on being straight and petrified of STDs. Don't get me wrong. I admired and looked up to some "Divas" and queens regardless, and are friends with many to this day, just some of it wasn't my scene. Again getting dressed up and feeling pretty satisfied me, but it didn't mean you still weren't more than curious or yearned for more. Even today I would give some of these ladies the shirt off my back, but for comparison purposes I was in elementary school and they already had graduated from college. Really I was just happy to hang out, party and make some connections. I was a semi-regular on lots of weekends at some hang outs and parties, meeting all kinds of club kids, other CDs and lots of people from all walks of life. I did at times tend to hang out with the less advanced CD group, but sometimes that can be depressing as it can consist of husbands out without their wife knowing, or worse cheating on her, but often they were more down to earth. It was on a night that I went to a party out on Long Island that I needed to get away from some really uncomfortable conversation that I left early. I was not into "being with" other CDs which is what she was interested in, so when after nicely declining a number of times, I went outside to get away and then for a walk. If I wasn't worried about being completely sober and a DWI stop, I would have got in my car and drove off, but I knew that wasn't wise. I had only had a few drinks but it was still too early, and even back then would never put myself in a position of driving if I was even the slightest bit certain of my sobriety. Reality is maybe I should have or just done something different but I am that person that always seems to learn the hard way. These parties were private and safe environments, so sometimes there were opportunities to go a little over the top, which on this night I was guilty of it. Mostly what I was guilty of was wearing way too much makeup and making my boobs exceedingly large as they were things I wouldn't have done in a club in a more mixed crowd. I was also in a platinum bob wig with bangs and in a white, form fitting stretchy mini-dress with white pumps, so sure I was trying to be a little sexy. This would be not abnormal for the party and far from even close to some outrageous outfits you'd see at these things, but not exactly how you want to be trotting down suburbia streets late at night. So I was only a few blocks from the party just walking and minding my own business when a convertible full of guys passes me and they are yelling out as they drive by me. Now I've been yelled at on the streets of Manhattan before, with comments like, "What's up babe?" or even insulted like, "Hey butch," being clocked, but typically you just walk along letting it roll off your shoulders. I walked day or night and through both busy and quiet areas and knew places to avoid where pros worked or you could get in trouble, but this was residential suburbia. I knew it a little bit, and really had no reason to be worried. Unfortunately around the block again they came, and then this time they slowed down, trying to strike up a conversation. I was polite, just saying no thank you, and then they actually said goodnight and I did the same. Fifty feet of driving would at most be all they did before they stopped and then a guy is yelling back at me to come and get in. "No thank you, and take care guys," was all I said, waving them off, and looking down at the pavement so not to make eye contact until I could see their reverse lights come on. Then it got lewd, as I heard, "Oh you are getting in alright," and, "Come on let's have some fun tonight," as then I began shitting my panties. I was about a house and a half from a corner as I'm thinking these guys are about to back up and then I speed walked as fast as I ever had in heels and turned down the residential street. House lights were the only things keeping it lit. I was sprinting now in heels the second I was away from their sight, but I could hear their engine backing up and hear them calling out. I don't know if they wanted to just fuck with me, kick my ass or have their way with me, but all I know is they were behind me in a car and I ran from the sidewalk into someone's yard behind their house. I could hear them talking as I was in a stranger's yard, hiding like I did something wrong and could still hear the car moving. I was petrified that they were searching for me and then hopped their chain link fence into the next yard on the other block. Amazingly I didn't snap my ankle but someone woke up with a white shoe with a broken heel in their yard and the other good one tossed behind their shed. Through that yard I sprinted past the house and then across the next street through the next yard before I just hid behind some shrubbery and in back of a freestanding garage for what seemed like an eternity until I heard nothing but crickets for at least a half hour. When I finally came out, I ran to my car and there would be no anxiety about being tipsy, as I was wide eyed, sober and absolutely filthy. Disheveled and rattled with holes in my stockings would feel like I was dressed for the Oscars, never happier to drive home into the city. I remember the only lucky part of the night was finding a parking space not that far from my apartment, and in I went shoeless without a care of how I looked. I cried in the shower that night, kicking myself and just wanting it to all be over. That next day would be a purging of everything female I owned as I was done with it, and tossed a few garbage backs worth of stuff in a dumpster. I didn't return calls, alienated some friends I shouldn't have, and in general was done with the whole lifestyle. It's during times like that though that you learn who your true friends are, because even when you don't talk to them for months, you still can talk just like it was yesterday. So eventually I got over being frightened, opened up to some friends who were amazing to me, and then dated a nice girl for a while, but it didn't last. It was actually about eight or nine months from when I purged every feminine piece of clothing I owned, telling myself this was all wrong, but the desires just had become stronger. That part I knew. Back to walks enfemme and I moved to a new neighborhood that made it easier to go out dressed. That was not the purpose of my move, but it helped things click and I was closer to some of the people in my support system. I now lived in a more mixed area (gay and straight) and got a little more into clubbing now. I always loved clubbing, but even more so now did not always have the guts to go alone enfemme, but time and friends eased that too. It would be at a big party that we went to as a group that a friend found in the Village Voice that my first true male "encounter" would occur. So back to the "mental side of it." Was I curious? Yes. Was I afraid it would make me gay? Terrified!! And a few of my very good friends were gay! Was I attracted to men? Mostly no... But somehow you feel different when dressed. When you feel pretty! Especially back then. Did I have crushes at times? Yes. One especially that I was a little fixated on. There was a guy that hung out with our group whose brother came a lot, and I always thought he'd be my first. He flirted with me so many times and I wanted him to be that first. He was more of a rocker type with long hair and used to be in a band, which I always thought was cool, and we always hit it off. Couple times I thought this guy is going to ask me out or something is going to happen here. I knew he had been with a girl like me before, but it just never happened. I later heard he was interested in me and thought I was attractive, but a prude looking more for a "Kelly Bundy type" and I was blonde, but not blonde. It fucked with my head a little at the time (which was already a bit fucked up). Like you want to look sexy, but its so much more than that what's in your head. Did I go back and forth in my own mind if I should, or wanted to kiss a guy? All the time, and for years! But then guess what happens when FINALLY a guy wants to kiss you????? It was a Saturday night and we went to an event/party that my friend brought us to on the lower east side. She was kind of the ring leader and organizer of going out. She was so plugged in with the nyc scene, clubs, events and everything happening. She would tease a few of us that without her we'd just dress in our bedrooms, yank it and for some never make it out of the closet. A stretch, but she was a little full of herself and actually I'd say calmer now but still is. (Sorry had to get that in as she'll be reading this). Yes a straight girl, still a friend today and married with kids - back then you'd never have guessed it! It was a big place with a very mixed crowd where you could barely hear a fucking thing without your friend talking in your ear when you were on the dance floor and needed to hang at the rear bar or upstairs just to hear yourself think. On this night I was with a group of nine, so we hung out and danced together, which we always did. I had danced with guys in our group numerous times before, and always joked around with them. Mostly we danced in groups and I was not their only CD friend, but the only one on this night at least initially. We all harmlessly flirted and there were some hook ups at times with this group, but not by me as I had no interest at the time, and sad to say, but I think that was mutual. Really we danced and hung as friends. It was normal. Beside our group, I knew a few people from clubbing and so did everyone, as it was a really a great social event. Nine became twenty something, with people having a good time and before long we'd go back and forth between the dance floor and the bar area where we hung out. Back then the minute I started to feel somewhat sweaty I would stop, paranoid I'd be a wreck and two maybe three songs would be enough to make me perspire. There were actually a few people that night I hadn't seen in a while, so I was enjoying catching up, and at least when you came away from the dance floor to the bar you didn't have to shout. I'm a talker in general, and not overly shy once I'm engaged in flapping my mouth, so admittedly sometimes I forget to listen. Even at the bar when the music is blaring it's hard enough to hear, let alone listen when a lot of people are talking but it was a small group of us talking about places we wanted to visit, and I remember being really engaged in the topic. Engaged in it until I caught on that maybe this one guy's questions were feeling me out and then directed towards only me. We were still in a group, but it got a little more personal and I could tell by the way the guy was talking to me that he was interested. I'd been hit on before and been egged on by friends, but never did anything about it. The casual chat with a guy or dragging some friends out to dance with strangers I had done, but that's where it ended. I was not interested in being the dresser that they were interested in meeting to give them something I had no clue how to do, desire to give and only had received at a different point in my life. (Ok well of course I had a clue, but you know what I mean). I won't say his name, but I had met him twice I believe before through some of the same mutual people at a different club, but whether it was the alcohol or my state of mind, never had he looked at me like this. And if he did, I didn't catch it because I was pretty sure we never exchanged too much of a deep conversation but that changed now. Slow deliberate abandonment would be a factor as one of my friends caught on and eventually our conversation would be only between us. I think what made me feel comfortable was that he was sweet and kind, as he put me at ease with general conversation without being a jerk and then I got to wondering if he remembered me at all? I was pretty sure he knew what I was, but as smooth a talker as he was, you just want to think that he maybe he doesn't? Maybe you're just another pretty girl? I wish I could say he had me at hello, or charmed me, but instead being a wise ass, having a few laughs together and the way he looked at me were what did it. "Why don't I buy you another drink upstairs at the bar where we can hear each other better" in such a hypnotic tone would be his simple invitation, but then before I could even process it, the, "So you ready? And you have such beautiful eyes," in his Brooklyn accent would be a most basic cheesy line that did it. When I nodded agreement, saying only, "Sure, and thank you." I knew what it might lead to no matter how much I drank, so I'm not sure why I didn't, but I didn't hesitate following him away from my friends. I couldn't look at anyone or say a word, as I would have chickened out as I trailed him like a puppy dog up the stairs. I didn't start out to meet anyone on this night, but it was becoming more inevitable as I found myself thinking about it more and more lately, and it was a night where I did feel good about how I looked. I was in black mini-skirt, black pumps and silver metallic type top. Nothing really outrageous, and at the time after I purged so much, I think I maybe had like three pairs of shoes. I'm not going to say he was a hunk or looked like Brad Pitt, but he was not a bad looking guy. Dark, short hair brushed straight back, clean shaven and slim. Better than most that had ever hit on me, and he was probably an inch or two taller than me if I wasn't in heels. I was pretty good at makeup at this point in my life, and my thing if we were out under some club lights was to add a little shimmer to my eyes. I would spend half my time doing my face, blending my eyeshadow and I loved to line my eyes in a dark liner and wear big lashes. A hint of silver glittered eye shadow at my crease would certainly earn an assist to his beautiful eye comment, as if you were within ten feet of me it would be impossible to miss. My go to lip color was a brick red, over lined a bit. Back then I almost often wore my hair pouffy when we went out clubbing, as big hair was in and this was not different. It was an era of perms especially spiral perms, but I didn't have one, so I would curl my hair tight and then pick it out. I had it teased a bit and wore it from a side part with the parted side pulled back by a comb with some little faux jewels that sat above my right ear. This is significant because that's where it started, as with my hair pulled back off that ear it would be an invitation when he leaned in that first time, softly kissing my neck below my cheekbone. We had barely made it upstairs and walked to an open part of the bar before he made that first move. It was definitely for the best when it came to my nerves or more mindset, and I'll always wonder if he knew that as I think sometimes regardless of your gender, you just sense things. Even upstairs it was fairly packed as we just leaned in against the bar and there would be no major conversation like we went up there to have, as the busy bar would be a factor. In his defense, he did try to signal the bar tender a few times, but it would take effort and patience to get some attention. We were kind of wedged in a spot but not nuzzled against each other. Closer than downstairs absolutely, but you could definitely hear the other person much better. "Hope you're not that thirsty?" Would be about all he uttered as he leaned out over the bar and looked at me. "No rush." Would be my great witty comment as I leaned against it as well and we were facing each other. "Cool." He sighed and that's when he leaned in. "Me either." Those last two little words would be spoken in my ear, and then his lips would follow on my neck. He had leaned in a few times when it was much louder downstairs, so just the movement really didn't alarm me, but what would be more alarming in reality was I wasn't alarmed at all. I'd like to say it would be just like an old girlfriend doing the same, but it wasn't, as one kiss became two. Maybe the first kiss I couldn't have stopped, but I didn't pull back from the second as he slid his lips down a bit lower, digging his nose under my hair, kissing more towards the back of my neck. I liked him, so really it was just a time in my life and of course a little buzz didn't hurt, but it can't be blamed for me not pushing him away. After the second peck on my neck, I turned my face just a little and it was soon over as his lips pressed down on mine. I gave no opposition, and it's not blur at all, as I remember that night and that kiss vividly. It wasn't the softest nor the most aggressive kiss I've ever felt, but it will always be special, as I'll never forget feeling kind of fulfilled when it broke after lasting maybe two minutes at most. I remember being relaxed yet more uncomfortable when we looked into each other's eyes after it broke, but would last just a blink or two before he kissed me again. Really for me anyway, that was the moment when I had understood I was the girl kissing a boy, and he seemed to really like me, and like me as one. I don't think I really felt his hand on my back after our first kiss began or even that I reached around him myself, but once things are in motion, that's kind of all it takes. Just like when you kiss a girl you like the second time, you lean in it's always better once any apprehension is gone and that's how I felt, although in a way it might have been less about the actual kiss. Thankfully I didn't feel those initial butterflies that I have at times, so I didn't overthink things like I've done with much in my life, and thankfully he didn't hesitate to kiss me again, or I'm sure how my life would have changed. Or maybe it wouldn't? I don't know? Our second kiss would be lasting though, as we soon French kissed and it become more of a make out session. In a way you do slip into the role of being kissed like you've always wondered about, and become a bit submissive to the pace, just letting things happen. I'm sure everyone can relate to needing a breath, but not wanting to take it when you're really enjoying a warm kiss, and that's how it felt. You're consumed with the wetness, swirling your tongue and aroused by even the most subtle touch. He was not an overly aggressive guy, so to a degree he was a gentlemen if there is such a thing in a bar hook up, as his hand on my back would feel so different than it did when he leaned in to talk. When someone leans in to talk, you're almost numb to it as you do it yourself, but then that same touch while you're making out you are so much more sensitive to. My top exposed my shoulders and a bit, so that feeling of a hand on your vertebrae when you kiss and for whatever reason oddly atop your bra strap, does help take your breath away. But beside that, and maybe it's just me, but there's something about soft tender touches and one of the things that I've learned has always brought out the woman in me. The kiss and the soft touch in harmony if I like someone are both paramount or else I can't feel a connection. In time I really learned I needed them both to enjoy someone's companionship, and I just never thought about that when you're in the other role with a girl. Some may and some may not agree, and it could all be in my head, but I've always felt it's quite different to be kissed than the other way around. No doubt on this night it truly was, and guess which way I like better? We actually never did have that drink, so if you're reading this then you still owe me! No chance he is! Jokes aside, you can never take back your first kiss, and I may have a few regrets, but its passion and how it made me feel inside that are important. We actually had really great conversations when finally we came up for air and kissed again quite a bit more before I thought my bladder was going to explode. In the bathroom I was actually pleasantly surprised at how decently my makeup held up, with the exception of my lipstick, having vanished into his tonsils. Judgy and disgusting nyc bathrooms I'd already known too well, so quickly you relieve yourself, touch up the best you can and get the hell out of there before you're sweating profusely and look even worse. Problem is in my case just squatting and peeing like a racehorse you start to think too much, and then wonder if you could have held it, worried if he's still there. Some regret does race through you a little when you do have a moment alone to think, but I know it probably would have been worse to have been blown off after what I just did, so thankfully there he was when I got back. We talked just a little more. It was nice to still be looked at the way he looked at me, as we both knew it was getting late. We kissed lightly, and after that would be the first time I ever held hands with a guy when we walked back down to find our friends. I let go before we reached them, a little bashful and maybe more self- conscious, but a few judgy looks and smirks I expected as we kind of mingled back in with who was left. Mostly it was his friends and only two of mine, but after a little teasing about being gone so long, everyone was starting to say their goodnights and he pulled me aside, asking me for my number. Did I give it? Yeah. Did I wish it was a little more quiet and he asked me upstairs? If you ask me today then yes, but everyone would have found out anyway, and even if I didn't want to give it out.. which I did... peer pressure in no way would have allowed me to withhold it. After I did and after I knew everyone saw that without a doubt it was more uncomfortable being kissed goodnight in front of them than it was being kissed at all. The two people that would have ripped me the most though at least thankfully weren't there, and I know he didn't try to embarrass me but thank goodness I had already peed. So yes I had to give details to my friends in the cab, and couldn't fall asleep for hours when I got home. I was happy and scared and kicking myself but I had done it. I had kissed a boy. You over think it of course, which I'm always guilty of, and then whether I wanted to or not, I relived it all, having to spend hours the next day on the phone. "I'm so happy for you!" "So glad you finally did it!" "He's really cute and you'll be cute together!" "I peeked upstairs to check on you and saw you kissing him." "When are you seeing him again?" On and on with friends and it was wonderful to talk about, but fairytales are short stories and short lived as guess what? My phone never rang. Well it rang and I answered it, but it was never him, as he never called. I had an answering machine that picked up, and there were a few hang ups that week, but detective oriented friends and the rumor mill told me he had a girlfriend, and I wasn't her. You can beat yourself up and question things about what ifs, but in the end what does it matter? and really I'll never know. What I do know is it was still memorable to me, and at least I wasn't just used as a crossdresser someone wanted to screw. I was treated like a girl he was really attracted to and interested in? At least that's how I'll remember it anyway. I was a little hurt and down about it for a few weeks, but I did get over it though fairly easily and hooked up for my second kiss only a few weeks later. This time it was local bar on a Friday night when I was out with my friends, and he was the one alone out drinking. He was in town on business, or so he said, but from Chicago and for whatever reason was focused on me from the minute he met all of us. Everyone was made up, and I think looked pretty good, but I was actually the simply dressed of everyone, in a jean skirt with heels, a tunic and my hair was straight. We weren't going clubbing, but just hanging out having a girls night and he bought everyone a round. Five of us bullshitting with him, but things just clicked. There was something about the attention, and he was a big, strong guy which for me until that night had not been much of a turn on. Add being the center of someone's attention in front of your peers and that you kind of feel delicate and girly in his arms, and then whoaaa! Kiss number two is amazing, and I felt so small and feminine in his arms. I learned I've always loved that feeling. I'll always remember measuring my hand against his palm to palm, and even with my nails fairly long with tips, they weren't even close. The guy had like catcher's mitts for hands, but was so nice and kind of the gentle giant type. But guess what? When you feel against your stomach through your top what he had in his pants press against me and you know he's only in town for a short time? Yeah you make an excuse that it's late and your friend is your ride, but you'd be back tomorrow if he wanted to meet up again. But of course even your excuse is bad when he sees you pile in a cab, and of course I wasn't going back anyway. Even though I liked him and it still did cross my mind. I actually felt bad about that right after, and I pretty sure if he wasn't just on a visit, then a good chance we would have gone out, and it would have truly been my first real date. There would be a third kiss about two months later which actually sucked, and this time I slipped out the back door. My friend (who was a GG) brought her boyfriend and his friend to a club, and really I should have known he was wrong for me, but it had been a while and at a time I was thinking about meeting someone again. I didn't want to just hook up again (which of course I did) but really was focused on trying to see what a relationship would be like and have an actual date. I had resisted another hook up the weekend before, but this seemed so right, almost like she wanted me to meet him and was friends with her boyfriend, who was a great guy. Sometimes you see it but you don't, as he was so good at flirting and for whatever reason kind of knew my hot buttons. It was a night where I loved my look. My hair fell just right and i was in a dress I had been dying to wear, and that night finally could. Really you're confident, happy to be out and almost hoping someone sees you the same way. Well he kind of did and didn't hide it, so I was into that. He was buying me shots and was a bit touchy feely, but I kind of let it happen, as I was interested. Still to this day I am a bit of a lightweight so I did pause him from getting me hammered, but that takes you to the dance floor and then to a corner table where the inevitable occurs. The inevitable though was consensual, and started out decently, but I just sensed there was something wrong about it almost from the start, and it took maybe only thirty seconds of kissing to figure that out. Regardless of who it's with, I like kissing to be actual "kissing," more like soft and wet, even when more aggressive, but this is like off my lips half the time, almost like nibbling or suckling, and it was just weird. Sure maybe I'm measuring this guy against other kissers after the fact, but it just seemed terrible. He was rougher, but not in a good way, and part of that was I know that it was my first time kissing someone with facial hair, but it really wasn't that. Touchy feely ok, and I've now let this guy touch my ass like the others didn't, but it's my first time making out sitting like this in a tiny kind of half booth. A hand sliding across my ass starts out ok, but he was forcefully grabbing me and that I didn't like. It actually hurt the way he squeezed my ass and inner thigh, and I'm saying to myself am I that much of a girl now that it hurts that bad? And then what do I get from him when I say, "Go easy please?" I get, "Sorry, but you're so hot, and it's pretty private back here." Boy or girl and even if you're kind of into someone, sometimes I think you just know that maybe you're on different pages if that makes sense, and I didn't make much of his comment, but in retrospect I should have. He was not a jerk per say, and we just had such a really hot dance before this, so maybe that was teasing a little but having to work to reel him in to enjoy being kissed? Sure guys are going to get handsy and it takes some work to keep them off padded things you don't want fucked with. But it's maybe five minutes, and I'm not feeling it. "Easy ok?" I think was all I said. "Ok, but you're teasing the shit out of me?" He says as slides that big sweaty hand on my neck and almost points my face down at the table. I should have elbowed him in the face, but I knew it and I didn't want to believe it or accept it, but when you know then you know. I wanted to convince myself that he was the friend of a friend, so he was not just out looking for a blow job, and I was a girl he liked, but shame on me. You never want to feel like it's the case, but you can't be na?ve. "Not that girl." Was all I said and then all I did was slide away and get up, grabbing my pocketbook, delivering no more than a dirty look. I didn't look back and I'm pretty sure he didn't chase me, as I just went right through the crowd and out the door. All I did was walk and kick myself for what I had let happen, but I had no one to blame but myself. My friend felt horrible when I told her the story that next day, but I didn't blame her at all. Her boyfriend called me and apologized for his friend, offered to buy me a new coat (which I had left there at coat check) and told me I should have kicked his friend in the balls. That he didn't deserve, as it wasn't like he treated me like a dog, but after you think about it a lot as time goes on, it really does hurt. It would not stop me from getting dressed and going out after that, but it did change my mindset a bit and I was soured on a lot of it. I still enjoyed feeling pretty and sexy, and thought a lot about meeting another guy, but to make a long story short, I just wasn't into it. I dressed less frequently and avoided some of the scene. The third kiss as a girl would be the last one with a guy for long time. Eventually I met someone I clicked with, and that totally put a pause in my dressing. She was perky and pretty and an amazing girl. We fell for each other, and everyone needs some love in their life, right? She was the sister of a friend from high school, so I was nervous about opening up to her and worried about my other life being more public but eventually I did. She wasn't overly bothered by it, but also not thrilled, and the more we talked the more I knew it was not something we could share together. I was getting near 30, so you think about getting serious and my family loved her. My mother was thinking finally! that she was the one. After a while it did get serious, and I did start purging some things. Things I was thinking at the time was ok I'm not a club chick anymore, and then little by little you toss more and eventually just say fuck it. After months and months with her, I had tossed it all, knowing it would not work with her. But guess what? I was wrong about her? Wrong about what I wanted in a relationship, and glad I didn't cut my hair as short as I was going to. She was trying to change me (not in a bad way or because of anything feminine, but because I think it was her way of molding me or reeling me in). Unfortunately I'm more of a rebel than I am conformer, so that wasn't going to fly. Really it had nothing to do with her, but once she was gone the desires to dress were back and stronger than ever. Really even though I didn't miss dressing (that much) when I was with her and felt happy, but I don't think the desires ever really left. Actually I know they never fully did, but in a way they kind of lived through her. (One of my therapist's theories that I believe is right, and I have had two in my life. Both of who have agreed on nothing, but I could write a book on just that, and thank goodness I didn't do much of this because I got better advice and comfort from friends)! Simply I loved to look at her and would study her sometimes. She was beautiful. I was really attracted to her and it was more than looks. I did love though that she was the creative type who just knew what to wear and how to put herself together. Some girls know how to do that and some don't, and that's always attracted me. She could put on a lot of makeup or almost none, and it just seemed right with how she did her hair or what she was wearing. Don't get me wrong. She was high maintenance as my mother would say, but that worked for me except probably was part of what kept us together longer than it should have. I did think for a while I was going to marry her but .... Nope! Not meant to be. In the end it was a painful break up, and like any break up that hurts you need some healing time and even though I ended it, I was no different. I had packed a lot into my late twenties, and definitely did a lot of soul searching. How long does it take you to know what you really want or to figure out who you really are? My answer: Your entire life! But that's just me, and if you look at the trends in my life, I'm always about a decade behind. I see these kids on youtube or TV that know they were born a girl by eleven or twelve and are transitioning plus kissing boys as teenagers? Maybe I should have known, but I didn't and yup, a decade behind! At least!!!! So as I healed my mind after my break up, I didn't just jump back into dressing again, but I wanted to. I actually traveled a bit which helped me, but didn't have as much vacation time as I would have liked, so that was a temporary distraction. I still hadn't re-invested again in any outfits,so didn't dress either when I traveled, even though I was tempted to buy stuff, but I resisted. I resisted outfits but what I couldn't resist was to finally shave my legs. It was a release, and I hated them hairy. I hated seeing them in my shorts like that, and I'm not even really that hairy. Not sure if people can relate, but for whatever reason it just grossed me out and I just did it. But that's all I did until I got back home and for a while. I did rekindle some old friendships with LGBT friends, some of whom were still my friends during my recent relationship, and others that I had been more distant from. It would be more the ones I hadn't seen in a while that had more of an effect on me, as some changes I would never have guessed had happened. One much older friend had told his wife and gotten divorced, but now had gotten serious with transition. Hormones and some procedures made her a different person, not just physically, but I could see how much happier she was. Another I knew might do it, actually did as she had srs, was getting married and you could see the sparkle in her eye. Over a few years a lot does change, but good people are still good people, and those are the ones I hung with. I didn't think I wanted any of that (hormones or surgeries) but it did make you think when you saw how happy they seemed to really be. I thought about that all week at work, but that Friday night is when I was ready. Ready to at least maybe feel as good as it did just to shave my legs. What always relaxed me, and still does to this day, is getting my nails done, so I did. I walked into the drug store on 34th street after work on a Friday night, loaded my basket with cosmetics and bought a pair of flip flops then walked down to Macy's and bought a pair of shorts, underwear and a top. I took the train home, made a nail appointment and put myself together. I hadn't been there in years, but once I sat there it was like I had never left, getting a mani-pedi. I didn't even go out that night, but instead just went shopping, and like old times just went walking around the Village. Saturday night I did go out with friends, and eventually I began to build up my wardrobe again. It was a slow process, but I was rushing nothing, and I was a different girl. So I was clubbing a little, but not clubbing the same way. I wasn't drinking too much, and I wasn't in love with how I felt about myself. I wasn't heavy, but I had gained some weight and I hated how I looked in so many things. I had also put on some muscle during my prior relationship, so that even bothered me more than a little flab on my belly. Years back, even the little man muscles I had used to irk me and not make me wear certain sleeveless tops, and now I couldn't at all. I mean I could but I wouldn't. I had also fucked up my hair a little, not cutting it so short but still losing a lot of the length and layering, so if you can picture it, I was in between a bob and something that made just a small pony. Really I just couldn't do what I wanted to with it for a while. (Take a look at Bryce Harper these days and you'll see it. It's all I could think about when I saw a summer camp exhibition game. Horrible and in between and almost exactly like mine except in a picture it ash blonde). I needed to get my shit together, and I did. Sometimes girls need a makeover and a new start after a bad breakup, and in some way I did relate. My makeover was to get a little serious to see if this girl in me was supposed to be who I was? I did see someone about the mental side of it now for the first time, and I don't think it helped except to talk to a stranger about it. That didn't last, but what did come out of it was investing in myself. I was good with makeup and hair, but I knew beyond my routines and what I had been taught there was still a lot more to learn, so I could use some formal training. I had always been conscious of my voice, and people always told me it was good the way I worked it, but I wanted it better. My vocal training until then was advice from a friend that used to sing, and recording myself on my answering machine over and over. I spent money on more advanced makeup lessons, a vocal coach and figured instead of spending this on a girlfriend, I'd spend it on me for a change. It wasn't that much money and not even intense, but helped me big time. I enjoyed it and I learned more than I thought I would. I did diet though like a fiend, and I was already into working out, so losing weight wasn't hard for me but it was a process that was new. The more I talked to my friends and girls that made changes in their life, the more I wanted to know shit. I didn't take hormones, but I was close to it and I really got super educated. I didn't cut off any more of my hair's length but instead about six months later darkened my natural blonde hair for no other reason than to not exactly be me. Try things as a brunette. A little different cut on top mostly, and it wasn't really that drastic at first as girls at work told me they liked my hair gelled like that, so most barely noticed until I told them, but in time I did go even darker. Try things that work on Valarie Bertinelli, my stylist would say. You're Italian and have same shape face. I wasn't in love the ideas at first (but she was right) and was more into Sabrina Salerno's style at the time. Loved her hair and fashion and knew I could never look like her, but i did try to emulate her a little. And Cindy Crawford was everywhere and in every magazine. I studied a lot of her looks and my makeup lessons were huge because I learned about all the changes I needed to make with my hair darker. I was never clueless to what I was doing when dressed, but it would take me well into the next year to feel truly better about myself. About how I looked and how I felt. I was still clubbing. I was still hanging out enfemme. I wasn't hiding or pouting, but kind of evolving and working on things, but those things were me and not guys. Or girls or anyone in that way. I was 31 before I felt ready to "get back on the horse" again and meet someone. It was not like it again hadn't constantly crossed my mind, but I was a more "serious" woman, if that makes sense. I was not going to just hook up. I was not going to be treated like a boy in a skirt. I just wasn't, and I'd talked to plenty of guys in bars and at parties with my friends, but just did not want to hook up. Really I didn't click with any or very very few. In a way I was a bit of a prude at the time. But guess what? No I didn't just hook up, so don't think it!! Actually I met someone though that I liked. I met him the first time at a home party/dinner time into the night barbecue type thing much earlier, and he couldn't have been nicer, but that was really it. Our friend would host these mixers in his house and yard in Brooklyn a few times a year. What a place this was and is. The old friend of a friend thing yes, and just a nice night with everyone kind of mingling. Just in this case the friend of a gay friend, so I shouldn't have been jugdy but typically? You know? Really he didn't seem gay, but I wasn't looking at him like I was curious about him, and we were in a group conversation. Nothing memorable in the first conversation as you walk around and bullshit with people, but then I was back in another group chat with him again a bit later in the evening. After a while though I just got that vibe that he liked me, and I kind of found myself wondering what his deal was. There was some sports talk, but you can't go one hundred percent on that, and he is a little inquisitive about me. It was a night I felt good about myself, like I was one of the prettier girls there in these strappy new heels I was showing off to my friends that I was in love with, and a summery peach skirt but of course that can be in your own head. My hair was decent way down my back now past my shoulder blades, except for some top layers near the crown where it was a little shorter and curled back teased a bit from a side part. (See Kelly Kapowsky hair as that's how had my layers cut on top, but I look nothing like her. I wished though)! I used to love my big earrings, and I remember having in my pan earrings as we used to call them, as they kind of looked like symbols or pans, and you'd tease your hair off your ears a little so they'd look prominent. There really wasn't any noticeable flirting, just general conversation getting to know people and it's not like you're trying to not be clocked at a party like this, so it's relatively relaxed and mostly everyone knows everyone's deal. Sure you are still not identifying as anything but female, so sometimes you're self-conscious about it talking to guys, but with him he treated me like every other girl in our conversations, so I wasn't on guard about it, then I'm noticing he's looking at me like a weird way. If its just that I'm being sized up a certain way as a dresser against others I don't give a shit, as I'm like one of five of us here, but then he says "you kind of got a thing? Like near your eye?" and points towards me. I always had that nervous habit, especially when I had side bangs like that sweeping my hair off my eye, and in my head I'm like "Fucking cheap ass glue did seem a little dried out" and my lash is popping off. But literally before I can even blink, he's just "Don't mind me, ok?" and reaches up, pulling one of those fuzzy white wishes from the edge of my hair. "Oh thanks," is all I can say and he flicks it away. End of issue. Was that a move I'm wondering, but it wasn't (so he's said much later on) and we talk as a group for quite a while longer, but turns out his girlfriend eventually shows up with some friends later. I wasn't looking to date him at the time, but was thinking he was nice, I liked his look, and they just didn't seem right together. Next day though my phone rings and my friend did bring him up, but he always did that, mostly baiting me for reactions to anyone I'd met, and I told him to just fuck off in a joking manner like I always did. Did I like him and think I'd like to have a conversation with him again? Yes. Was it stuck in my mind or was i obsessed with it? No. He was nice. He was cute. But I wasn't smitten with him. I had felt this way about some other guys before, and was just so guarded and nervous about shit. Next party at that house though was a few months later in the early fall, and sure enough when I walked in there he was, and he remembered me. I was the wish girl. "Hey, the wish girl." As the joke started. "What you wishing for today, Jena? I'm a pretty good wiseass and good with comebacks, but he did catch me off guard. I literally just got there and had barely greeted some friends and I got ripped on. "Wish I could come in again?" Was the lame best I could do follow up line. I won't get into it in this story, but that and some of the jokes that have gone along with some of this still follow me around. Those that know me personally know exactly what I mean, and please keep it to yourself. So literally it didn't bother me, but was more annoying having to explain over and over all that happened was that a stupid fuzzy wish thing was pulled from my hair. Is there any girl, trans or not, that maybe hasn't used too much hairspray, which was probably all it was, and I know even today I'll go a little overboard with products when I know I'm going to be outside or where it tends to be windy. But I'm a firm believer that shit happens for a reason, so having a puffball stuck to my head is in a way how I met my first boyfriend. Did I expect him to be at this party on that night? Yes. I heard he would be. Did I want to continue a conversation with him? Yes. Was I thinking it would advance further? No clue, and not too worried about it. Interested in a few others at the time, but still not jumping into things with both feet. I really didn't engage him at first after being ripped on, as when we came in the guys were downing some beers and being stupid. It wouldn't just be me that would be called out during that time when walked in, so it wasn't like I was the center of attention. When I go out, yes I'm vain that I'm looking my best, but I'm still not the girl that's looking to walk in and cause a stir. I barely had gotten a drink though before he came over and apologized if he had made me feel uncomfortable, so right away we got to talking and I laughed it off. What started as a few minutes of one on one chat didn't last, as so many people were arriving and one on one became a group, being pulled away in different conversations like at every party. So really I just mingled and bullshitted with my friends like we always did but I did catch him checking me out. I was a lot more dressed up than the first time I had met him, as we were planning on heading back into the city and going out to see a band that night, but that didn't happen. I was in like a mustard, one shoulder top and black leather skirt with gold criss cross strap type stilettos. I had my hair more sleek with a little wave and turned under from a side part with bangs in the front. Harder to describe it all, but straighter, except you roll under your layers inward like at your neck, and I liked to do a thick side on the opposite if you wear a one shoulder top. (Fashion friends tell you shit endlessly, and the real commitment I had made earlier that month was chopping my fringe layer/long side bang to real bangs. Another story by itself, and I liked Shannon Doherty's look on Beverly Hills 90210)! Being dressed up was not abnormal at these things, as if you didn't look half way decent you'd be out of place. So many in this crowd worked in the fashion industry, and you always wished you had some of their hand me downs. What did happen though was that I kind of made it my business to be part of some group conversations he was part of, and then that did lead to some time one on one. I was intrigued. I wish I could say there would be witty "Wish" conversation and jokes that had me hooked on him, but not on that night and in a way I was glad. Sure we joked around a bit, but instead I didn't have to just hide under juvenile conversation and was able to see more about him. At first stupid things, but things that help make a connection. Things about people at the party we both knew that we could laugh about, and then things that just clicked between us. Turned out we were both picky eaters, had a lot of family similarities we could relate to, and liked a lot of the same things. Sports teams, tv shows, taste in music, that kind of stuff. I was like wow? Maybe? And I wanted to ask about his girlfriend, but in a way I didn't. But really while we were talking it was on my mind the entire time, and then I am rambling and he's not looking at me while I'm talking and staring past me, almost like I lost his attention. So I'm like "You with me, or did I lose you?" and I look back over my shoulder and I catch his one friend just turn away. I was thinking, tell me are these assholes making fun of me again? "No, he was just leaving," he said and I was like so much for this. Wasting my time again, and said "Did you need to go say goodbye, or is that your way of telling me you have to go?" "Oh no," he said. "We both took the train here, so no, but it was hard to catch what he was saying that he was leaving with your hands flapping like that." I had a good laugh, as I knew what he meant, as I am an animated speaker with my hands and it's always come with my heritage. "Sorry can't talk without them sometimes." Was about what I said and he could easily relate and then he seemed confused yet complimented me. "Me too sometimes, and great nails," was my compliment. "Went square this time?" I had to think about that myself for a minute, as my tips were round the first time we met. "Yeah square, and kind of bright, right?" I said, flexing my fingers and joking but on this night they were a bright red. "Not many guys would notice that?" "I always notice things, and even noticed you matched your toes this time," he said, looking towards my feet. "Great shoes too, Jena. I couldn't miss those?" Fuck, I'm thinking now, as my gay-dar was immediately up as what straight guy notices these things, especially your nail shape? And the toe color? I'm like shit did I send off the wrong vibe? and I know he likes me but maybe he's just looking for more of a gay-queen type. "Thanks. Brand new," I said, fucking disappointed, and he was so nice so I didn't want to be rude, but I just wanted to ask him, but sarcasm instead came out. "14th street if you want your own." He says I rolled my eyes and looked pissed, but that's I'm sure an exaggeration, but it broke the weird moment and got me the answer to the question I hadn't yet asked. "Good to know if I ever need to buy shoes like that for a girlfriend." He smiled. "But not my thing, and maybe you took what I said the wrong way, since just because some of my friends are gay doesn't mean I am." "I'm sorry, and so are mine," I said. "I was just .. and with the way you noticed things... and I knew you had a girlfriend, but these days I guess that doesn't mean that much." "Used to have a girlfriend, and no biggie," he said. "With who I hang out with I can't blame you for making that assumption anyway, and you seem like such a cool girl I was really just trying to compliment you." "Oh gawwd," was about all I could reply, wanting to crawl under a rock, even though I just got some answers to things I wanted to know. My fucking big mouth again! He looked annoyed though, and then it was like he was waiting for me to say something, but I didn't. "So I've been just talking to you for like an hour, and you didn't really think I was gay, right?" he asked. "No," I said wanting to just die. "Not at all. Can we talk about something else now please? Please." Please tell me I just did not blow it with this guy I'm now thinking, as ok get it together Jena, and let's see if this goes anywhere. I was never at the point in my life where I'm like this guy is exactly the type I want to be with, but now this was the closest I ever felt to that. Well I'm sitting there with a guy that's nice, definitely interested in me, freaking good looking and seems like the type I've been wanting to meet for maybe five years, and I'm fucking it up. Thing is even if you feel good about yourself looking pretty or making a connection, sometimes you just don't have that type of confidence, and I still didn't. In retrospect, he said we never had an awkward silence but it felt like a month, but what would be a sign of things to come was he always knew how to put me at ease, and he did. "Sure, and I noticed you changed your hair a little too?" he said with a smirk on his face. "I like it, but maybe not as good for catching wishes though?" I wanted to kiss him right there, but just smiled and was even hoping for a hug or to have him clutch my hand, but I got none of the above, so had to be satisfied with us getting past the bump in the road. In time he'd be used to my mouth causing disputes or getting us in trouble at times. Reality was that we talked a little more and then got up together to get some picky food and drinks. We were in some other group conversations as the night wound on, but besides a trip or two to the bathroom we'd be inseparable. The only troubling part would be he would have a few chances to ask me to go for a walk or make a movie, but he didn't, so I did get anxious about it. It had been a long time and I still wasn't looking for just a hook up just to kiss someone, but I felt so comfortable with him so I'm sure I would have. It wasn't the end of the party, but the crowd was kind of dwindling and then finally he asks me. "So I know you're probably going to go soon, but did you think we could have dinner together?" he said with a grin on his face. I'm like fucking finally! in my head, and did this bastard make me sweat it out? Was that my punishment for my thinking he might be gay? "Dinner?" I said, having to be a wise ass. "Tonight no, I'm freaking shot." "No, not tonight." He laughed. "I'm thinking how's next Saturday night?" "Next Saturday?" I'm almost punch drunk now from waiting. "So you're asking me out?" "Yes," he replied and I actually did see him get a little nervous. Then I as much as I wanted to, and was going to of course say yes, I had to do it. I had to fuck with him just a little. "And if I said yes, then where were you thinking we'd go?" I asked, trying to keep a straight face while inside I'm so excited. "I don't just go anywhere?" "Well we seem to like a lot of the same food, so any place you want?" he said as he's getting serious. "I'd just love to take you out, so could I get your number? and I'm free next weekend either day if Saturday is no good for you? I'll take you anywhere? Anywhere you want to go?" He had me well before that, but he really had me with anywhere. You're always worried that maybe guys are worried to be seen with you in certain places, or maybe worried you won't pass and they'd be uncomfortable but for whatever reason, I didn't get that from him. "I'm good with anywhere," I said with a little smirk, so happy inside. "And Saturday's perfect." I opened my bag and it felt like I dug around for a month to find my pen before ripping a page out of my little contact book and writing it down on . A content, somewhat relieved end to the night would be a kiss on his cheek when I handed it over, and kind of an awkward goodbye followed by that dreaded 'call you tomorrow' promise. You're still nervous about it, but this time I was confident and the next day my phone did ring. We actually had a nice conversation and then it rang a few more times that week leading up to our date. Yes I did feel giddy that night I went home and my brain was racing a little that week. I think what made it easier would be our conversations that week, as he was so easy to talk to and that just put me at ease. I didn't freak out the day of our date (with the help of my cousin) or panic too much as I was pretty prepared and glad I had those earlier hook ups, or it would have been different. We had picked a restaurant in Little Italy with his suggestion that I had been to before, so I knew it and that also helped me feel more comfortable. I had a good idea of what I should wear there, and had time to get my shit together, which I did. Nice restaurant date night dresses though I really wasn't sure I exactly had, so the blessing was that I had most of the week to shop. I really didn't get dressed too many weeknights, so it would be more pressure to hurry home, get me together and then shop. Instead more of my angst would be which of my new purchases that I should wear, but I've always loved shopping and adding to my wardrobe, so it wasn't like any of it was going to go to waste. Got my hair trimmed on Thursday just to tidy the layers, and took half a day Friday because that's when I could get the manicurist I preferred. I could have gotten the other girl I used sometimes that night, and really didn't need the haircut as I was just there few weeks prior, but it would be as much mental as physical preparation. When you wait this long and you're this resolved to something, what would have made me freak was if I felt unprepared. So I couldn't be. Two of the days he called me that week he had to leave messages, and then I'd call him back late when I got home, so we'd start talking at ten at night. I didn't want to say I was home that late wearing out the stores shopping or spending extra time prepping for him, but that's what it was, and truth be told I was relishing the entire pre-date experience. Our conversations had me looking forward to it, and my friends had me so excited about it. I loved everything I bought, but eventually easily picked my dress. I probably wrestled more with what shoes I wanted with it, and what jewelry, but I knew exactly how I wanted my makeup and how I wanted my hair. It was not like that a lot of my life just to go out, as I wrestled with outfits or hair, but for whatever reason for this night and this date I just did! My cousin who is my best friend, came over that Friday night before to hang out and then slept over, which was her way of serving as a distraction and provide support if I needed it. She was like did you want me to help you with your makeup or curl your hair? but I just declined and she knew why. Because I was way better at it and normally the one that did hers? LOL but true. No, because I had to do this myself if I was doing it. I just did. After talking with him all week, I was more scared I really liked him and what that could mean in my life than I was to finally go on a date, but that was trumped easily by desire. Yes I was kicking myself, like what are you doing here, Jena? Are you like a fucking teenage girl with the hots for this guy? Ok, a few flings, but that doesn't seem like this? And that's without other things that maybe he'll want or worse I've thought about a lot and talked to my friends about a lot of things. Gay guys and girls are way worse than boys with the locker room type stuff, so you think about all this way too much? And you're thinking if it was the old you? The one not in a dress all made up, then like he'd be a guy you'd be friends with. Like to hang out with. Athletic. Funny. A good body. A guy the girls would be into. Jeez that's my type, and I can't stop thinking that. Holy shit? Accept it, girl. Yeah you Jena. And then if you actually do and if it goes well like you want it to and hope it does and even expect it to? Could you actually be someone's girlfriend? How the fuck could you pull that off? or could I even see myself as one? A girlfriend like I've enjoyed having and looked forward to be with? Big fucking challenge or a stretch, or is it? Another million dollar question that you kick around in your head or kick yourself for even getting yourself in this pickle, but as much as you wrestle with it, the desires outweigh the angst. You kick yourself again and again but the desires don't leave. As the week went on, they got stronger. So really you just want to feel good about yourself and be prepared. And I was. I wasn't chickening out. I was happy to have someone to hang with Friday night and without her I would have tossed and turned more, but I was still going through with it. I was excited about it and focused on enjoying the experience and feeling pretty. My dress was a few inches above the knee, so short, but not super short. A halter dress in royal blue color. It was a blend but had that silky shimmer and I just loved the way it looked on me. I felt thin in it, and it's cut pinched in enough that I liked how it framed me. I also already owned a lacey royal bra and panty set that complimented it perfectly, almost like I bought them together but I didn't, and it wasn't like I'd be showing those off no matter what. It was like it was all meant to be, and I just knew I picked the right dress, as the bra easily converted to halter and worked perfectly with the expensive silicon inserts I had, which made me a decent B-cup. They were also kind of heavy, so that for me always as well has helped with my mind ,as you don't get as uptight when you get pressed (Which in this case would be to kiss which I'm hoping , and i was self-conscious about it at times in certain outfits). There was no cleavage to be worried about in this dress, just your shape, and I was really good with my body for a while now after being so committed to diet and exercise for the last year and a half. I had my hair in a middle part and curled the back and sides before finger separating it just to give it some body. I just picked out the crown ,which just gave it a full look except for a thin front layer of bangs which looked so perfect, so I'm glad they were just trimmed. Kind of softer curls instead of kinkier, which I actually hadn't done it a lot like this, but it did fall nicely, and listen to your hairdresser's ladies about what works with your face shape and texture. Was not my original thought, but one of a few suggestions that I liked that Thursday. I was still mostly favoring my lips in darker reds, but did listen to my cousin on this one, doing a slightly lighter pinkish cranberry lip, which I loved with my dress. I did do a thin water line blackout liner, with my never leave home without them big fake lashes and prominent smoky eyeshadow. A speck of royal color, yes at the crease, but I was NOT that blue eye shadow girl if you're thinking that with my dress, and on this night I'm trying for a bit sexy, yet a bit reserved look. I could have gone bigger and curlier on my hair, wilder or more dramatic with my makeup and skimpier with my dress, but it really wasn't who I wanted to be. I just wanted to be a regular girl on a regular first date, not the dresser being a bit wilder and going clubbing. Believe me there's a lot of temptation to go a bit overboard, but in the end I just kept to my plan and was smart to take a little input. I did do my nails that same bright red and square on purpose to invite a comment, and he did notice. Probably my biggest splurge were these black suede wrap around stilettos, as they were expensive, and then I ended up buying this little bolero jacket and bag to match but it all came together. I know I wore too much perfume and entire field of wishes would have stuck to my head with the amount of hairspray I had on, but I was worried about the wind waiting to hail a cab, and no matter how much deodorant I had on, I was concerned about sweating. I was fairly calm all day and I didn't feel nervous, but no one told my palms for whatever reason. It was a good sign when I did get a cab pretty quickly, and I crunched a few tissues in my fist on the ride. I wasn't that panicky until I knew we were getting close, and this part is embarrassing, but I can't control myself as I am passing gas in the cab. Not loud, but I think loud enough that the driver heard it as i see him glancing at me in the mirror and I'm thinking ok looks like he's about to meet the real me already. The classy girl! Thank goodness though that would be the end of a few not so discrete fanny burbs as we made it that last few blocks without further flatulence, so when the cab pulled away and I saw him standing there, I was good. I had not expected to be blown off, talking to him all week, so it would have been devastating, but still there is always that sliver of doubt. Relief. Exoneration. Just a feeling of wow? You crazy bitch. You really are doing this, this is really finally happening and OMG!! That little smile on his face though as he walks towards you just wipes away the butterflies, and it is surreal for a minute or two. "Hey," was about all I could say, and then you get the hello back, but then "You look beautiful" which lasts a lifetime. It really does. I'm pretty good with remembering all the details, and hopefully describing them well, but the next part of what we said was a bit of a blur, as I was stuck in the moment hearing that as we did exchange a few inconsequential pleasantries before I did take his arm as we went inside. I remember feeling proud just to walk with him, and maybe this is not the best example but almost like the feeling you have like you've accomplished something like walking out after getting a diploma at graduation. I just felt so sexy in a way, or more like the prettiest girl in the room kind of being paraded in if anyone can relate. It would be the first time a guy would hold the door for me like that, and also have a waiter pull out my chair. Just sitting there those first few moments it felt so nice to just take it all in, looking around and across at him. That vision is still vivid in my mind, and as you do look at him you're still thinking, "I really can't believe I'm actually on a date with a man." Funny part is we had talked all week no problem, but now we're across from each other and there was a bit of an awkward, "What do I say" pause. "How was your ride here?" and "Did you find the place ok?" and "Great choice of a restaurant," useless filler stuff as you're trying not to seem overexcited but you are. The waiter brought us some bread, suggested some wine which we ordered, and then said would be right back with our menus, as quite immediately then our date would get interesting. Well what broke any first date jitters would be him knocking over my water reaching for the bread, as into my lap went the water, so that's how it started. Five minutes into my date I'm jumping up from the table soaked, mortified and looking around, seeing half the place staring my way. In reality most of my life I had usually been the spiller, so I was more embarrassed than panicked, as i got up, flipped the ice from my lap and wiped myself with the cloth napkin. I actually calmed him down, trying not to make that big a deal of it, and just went to the ladies room to dry off. Of course the stupid hand blower was way too high, but it helped a little as mostly it went on one leg, one side of my dress and not into the middle of my lap. A little dampness, wet stockings and a little clumsiness were not going to ruin my date, but instead made for laughs, and I was long dry by the time we left. Beside that - Our meal, our night, our conversation and the experience was perfect. When we left the restaurant that night, I slipped my hand off his arm and right into his hand where we locked fingers. We didn't make it far walking, as the plan was to take a cab to a quaint place he suggested for a few drinks, but instead it was really when our relationship began. Our first kiss was on Mulberry street before we even got to hail a cab. Something about that kiss was just right as it wasn't too long but not short either, and I knew right away it was nothing like kiss from a stranger's hook up. I know part of it was that I wasn't worried about fending him off or kind of justifying myself to a stranger, and part of it was build up. I had thought about kissing him since that last weekend, and the wait would be worth it. I loved the way he always looked in my eyes and it was just like he was the perfect height (6'1" and I'm 5'8" flat footed). To be snuggled in a cab with his arm around me while we kissed a little more would be nice, but then he made me a little nervous when instead of the bar we were headed to, he changed our plans to go uptown. He later told me he was thinking about it all along (as long as things went well) and then I was still caught off guard when we got out near central park. It was actually a touristy thing I had never done, but a nice surprise as we went for a ride in a horse drawn carriage. I was still not there yet when it came to feeling truly romantic, or being romanced, but the thought was really nice and was a bit of a window into his character. As you can imagine, we barely picked our heads to see any of the scenery during the ride and even under a stinky horse smelling blanket, neither of us wanted it to end. We never did get a drink, but instead walked arm in arm, talking and kissing until it got really late and my feet were killing me. (New but expensive shoes and the next day I did have blisters, which barely ever happened). So first date a success, and it would be the start of a new phase of my life that I'll always look back on with fondness and all types of tears. He would be true to his word that he was never worried about taking me anywhere, and that did change my perspective on lots of things and really give confidence. Second and third date would be the next weekend and include my first time "like this" at a Yankees game Friday night (terrifying) and then my first time as someone's "girlfriend" on a triple date to dinner and a movie with some of his friends. (Not so bad as I knew one of the couples). And yeah what I imagine you want to know? The racy stuff. It would be two more weekend before I gave "pleasure" for the first time orally and it is as scary as it seems. He was patient and supportive and knew it was my first time and did not rush or push me. I wanted to do it and I invited him into my apartment, but as much as you prepare by practicing on items and getting advice on how to, you can't simulate it, and it took me a long time to get decent at it. Maybe I rushed it and maybe I didn't, but I knew as soon as I had him on my couch and was in a certain state of mind, I couldn't wait or I would chicken out. But really I was hot to do it. Sex on the other hand would come that next night and it would be a lot easier. When you really like somebody and once you're ready mentally to deal him putting you know what where it has to go, then you adjust and make it work. Again though this was another thing I had thought a lot about, rehearsed in my mind and was prepared for. Well, as prepared as you can be without freaking out. You still think a lot about what it means to give up that last bit of yourself, and it does turn you a little. And without giving away every private moment I cherish, I had on my lingerie under my dress and we planned on going out, but I knew we wouldn't be. Not my first time in lingerie in a bedroom by a mile, but of course first time like that for a man, and during the bedroom foreplay it's not that different. You're tucked, you're kissing and you're feeling sexy, but that's where it ends. You can't hide it forever, but you do the best you can and I was prepared (candles, lube, the bedroom) but you can never be fully prepared. You just have to let it happen. Sure you don't do much at first, and of course I've played around over the years, so it's not your first time feeling things there, but it wasn't that. Anticipation. The poking around stuff. You try to relax your muscles like you know you need to, but it's impossible. It's not so pleasurable, but you kind of don't care and then soon it is. The first time in a way it's like water torture, but then you're feeling warm in a way as it's happening. Feeling his flesh inside me, the way he touched me and talked to me made me feel like more of a woman that night. If you haven't been with someone that you really care about, then you might not fully get what I mean, but in a way it completes you as a woman. We all want to be loved. At least I know I did, but that's me. I'm not saying this was great sex for quite some time, as it was not so pleasurable physically, but it was mentally. But thing is you want it to be, so you keep working at it and you get there. And eventually, as you learn things, it's really really is pleasurable. Really you get to amazing places, and I did so much wrong (and still do) but you can't look back, even though we all have our regrets. He was my first for many things, and he changed my life. I'm not saying my life has been easy, and I haven't waffled, but I've never tossed out my clothes again. I am and will always be that girl that was a slow learrner, a decade behind, and I accepted myself during this period of my life. With him it was first time being shown so many things as a woman I could never list them all. Some good. Some bad. Some I'd still like to kill him over. LOL Like crashing my car (Cops were not as understanding, as now and you're explaining it is your car but of course you're not looking like it states on the registration). Like him always sneakily telling the waiter it is your birthday so you want to kill him when the staff comes over with cake and a candle to sing you happy birthday and he's laughing hysterically. Little pranks and little remarks but made you love and hate him. I can go on and on here, but I won't. Really it's mostly good. (And I'm not Taylor Swift ripping old boyfriends). First boyfriend, first vacation with a man, first slow dance, first kiss under the mistletoe, first kiss on new year's eve, first to buy be flowers, first valentine are the things that come right to mind. First class guy that never made me feel anything but special is really all that matters and how I'll always think of him. I didn't need to search for my next date for about two and a half years, and believe me for a long time I wished I never did. This I won't share in detail except to say I couldn't make the commitment I knew he needed, and those things become the hardest parts of the life that we live. Date me and with your next lover you will have a nice house, 2.5 children and a Labrador retriever. LOL Just of course not with me, and I'm three for three in that category. But the consolation prize of always having a special place in my heart isn't that bad.