Kristie's First Night Out free porn video

Kristie's First Night Out A True Story My name is Joe but my femme name is Kristie. I am now in my thirties. I am about 6" tall, 165 lbs. Over the years, I began to realize I had feminine features...a soft and delicate face, shapely legs and a thin waist. I began cross-dressing like many others, trying on my mother's and older sister's clothes. Starting out with just panties I evolved into bras, slips, pantyhose and then dresses, tops and skirts. Every time I dressed, I found my self getting excited which caused an erection, which would enviably end with a massive orgasm. Fast-forward: I am now on my own and have been cross-dressing for many years... but only in the privacy of my home. Over time I have built up an extensive wardrobe by purchasing items during the Christmas season and at a boutique in the city that caters to the transgender community. I became quite skilled in applying make-up and with my collection of accessories, I felt, except for my height, I would be very passable and would not attract attention. Never leaving the sanctuary of my place, I had always fantasized about venturing out in public, meeting another cross-dresser or transvestite and having a "lesbian" encounter. While searching the Internet, looking for friendly clubs that accepted cross-dressers, I was amazed to find a place called Connexions that was located in a town that was only a few miles from my home. Being straight and never been to a gay bar before, one Friday I ventured out to see if it what I read about this place was true and if I could meet any others who have the same dressing interests as I. When I arrived at the club, I was surprised to see it was located in a renovated train station. With its large, transit parking it was obviously busy since all the spaces were taken. Consequently I had to find a spot on the street. As I walked in the door and paid the cover charge, my senses were taken over with the sound of thundering music. The upstairs, Friday night dance party was in full swing with the DJ spinning the newest dance and house music. The darkened room had an excellent light show and the good- size dance floor was packed. Everyone appeared to be having a fun time.? In the front room there was a bar with about 25 seats and pedestal tables. In the back there were booths, a pool table and an outdoor patio area. I got a beer and started to walk around. I was getting disappointed since all I saw was men, of all different ages. Then, in the dimly lit room, over in a corner I spotted a group of woman talking. After observing them for a while, I realized that they weren't girls but boys, dressed as If they would be going to a fashionable, chic club in the city. I mean...these guys were dressed to the "nines"! I downed my beer got another and started to work up courage to talk with them. Going back to my observation spot, I became aware they had noticed me staring. One of them, an off the shoulder, long haired blonde about 5"8", waved me over. No turning back at this point, I walked over and joined them. She introduced herself as Susan and asked me what my name was. Since I was in my clothes, I answered, "Joe." She was finely dressed in a knee length, black-striped dress with nude pantyhose and 4" black heels. Her nails were done expertly and her gold bangles, necklace and earrings topped-off her overall appearance. She obviously had been dressing for long time because her make-up, posture, speech and female demeanor were perfect. We all introduced ourselves and talked a good while. I found that they all came from different backgrounds and occupations. They were executives and tradesmen. Some were married. Some were gay and some were straight but they all had one thing in common...the love of woman's attire. However, I found myself more attracted to Susan and wanted to know more about her. I asked Susan if I could buy her a drink and she said, "Sure." She followed me to the bar; I ordered her a Chardonnay and another beer for myself. I asked her if she would like to sit down, she said, "OK" and we walked around looking for a place to sit. As luck would have it, a couple was leaving and a booth became vacant, so we both slid in, opposite of each other, and started to talk. After praising her on how smart she looked, I found out her name was Tom and that she was once married and had two children. In her mid-forties, she had been dressing in private for many years without her wife being aware. On business trips she would take an outfit or two, make-up and accessories and dress in the hotel after business hours. Also having the fantasy of going out in femme, on a trip to LA, she got a motel room that was close to a friendly club. She explained how apprehensive she was but finally got the courage dress and go out. The next was history, since her enjoyable first experience has turned out to be a weekly obsession and she has become a regular here ever since. She finally addressed her desires to her wife who could not understand and quickly filed for a divorce. She has been divorced for four years and has a whole new group of friends. The waitress came by and asked if we wanted another round. With a wink at Susan and a nod by her I gave the girl the order. At that point Susan said, "You know about me...what about you?" For the first time I admitted to someone else that I was a cross-dresser, and have been doing it for many years. I also told her why I was here tonight...wishing to meet someone like you, who could take me to the next level. Pleased to hear that, she asked me to sit next to her, so I promptly moved to the other side of the booth. Her perfume overcame me in the smoky room and I moved a little closer until our hips touched. She didn't move away and as we started to continue our talk, the waitress appeared with our drinks. As "hokey" as it may sound, I offered a toast in her honor, hoping that we could see each other again! We continued to talk, drink and enjoy ourselves until we heard, "Last call." After finishing our drinks, I asked if I could escort he to her car. We walked out and on the outside she linked her arm with mine the rest of the way to her car. Once there we exchanged phone numbers and e- mail addresses and promised we would see each other next week and she would help me fulfill my fantasy of going out. She gave me a kiss on my cheek and we went our separate ways. At that point, for the first time, I truly questioned my sexuality. The next day, I excitedly called Susan and we started to lay the groundwork for our adventure. She knew of an old style motel, the single floor type where you could park your car right outside the door of the room. This was perfect since I was reluctant to get into an elevator or walk any great distance across a parking lot. She said she would make reservations and call me when she got there to let me know the room number. "Plan around 7:30 so we could make ourselves pretty before going to the club'" she said. I told her, "I will bring the wine." "Sounds great, can't wait to see you...bye," she responded. The next week was a crazy time. My mind raced in every direction. I started to question what I was about to do. Would it be the "bloom off the rose?" Would living my fantasy actually be what I always dreamed it would be? I wasn't sure...then I was sure. Back and forth I argued with myself about the uncertainty of the situation. Another words, I was getting cold feet. Friday came and I was still not 100% convinced when, at 4:30, the phone rang. Looking at the Caller ID, I recognized Susan's cell number and my heart began to beat faster. Picking up the phone, "Hi Hon," I said, "what's going on." "We still on tonight?" was her comeback. "Yes, see you at 7:30" I said. "We are in room 36, at the end...plan to spend the night," she concluded. With that we said our goodbyes and I dashed to my room to prepare. Always clean-shaven, I jumped, for the second time that day, back in the shower and once again shaved my face, legs, underarms, chest and pubic area. Playing close attention to the small strip of hair, "my runway", above my penis. Drying off, I powdered my self with Chanel dusting powder and dressed in my "Joe Clothes." Then I went to my special closet. Looking at my wardrobe I decided on my low-cut, basic black dress, with tiny spaghetti straps. Then I opted for my black satin, 3" heels. Moving to the dresser, I opened my lingerie drawer and selected a brand new pair of black panty hose with built in French-cut panties. I also grabbed a black thong, black half-slip, black bustier, and a black bra and corset (you can never have too much black). Also, my 34D breast inserts, brunette shoulder length wig, pair of black stockings and garter belt and a black negligee with a matching sheer robe. To the jewel box I chose a pair of clip-on, gold hoop earrings, gold bracelet and necklace and a pair of dinner rings. I also took my diamond heart necklace. Going to the drawer in the vanity, I selected the appropriate make-up, hair spray, brushes, etc., paying close attention to getting my ruby red lipstick and matching nails and best perfume. Finally, I chose my black, clutch handbag. All placed on my bed, I grabbed an overnight bag and carefully packed for what I hoped to be the time of my life! As the witching hour approached I grabbed my bag and went to the kitchen. With my growing my anxiety, my pulse rate was going through the roof. I decided to have a drink to gain my composure and strengthen my courage. I then went to the wine closet and chose my best bottle of Chardonnay. To the fridge I grabbed a 6-pack of beer and placed it in a cooler. Walking to the car was almost like taking the last mile. My hands were shaking and my knees were wobbling. Putting my things in the back seat, I got behind the wheel and took a deep breath. Started the car; backed out of the driveway...I was on my way. Even thought it was only a half hour drive, as I thought and fantasized, it seemed like an eternity. As I pulled into the motel parking lot I drove all the way to the back. There I spotted Susan's car, parked right in front of Room-36. Leaving my things in the car, I walked to the door and knocked. To my surprise, Susan must have been there since check-in time because she was beautifully dressed. Ravishing...she was in a black, velvet mini-skirt with a low cut white, silk top with puffy sleeves. Her blonde hair was up, exposing her long shapely neck. Black stockings and black heels finished her look. "Come on in," she said, "We don't want to be the last ones there." "I'll get my stuff," I replied. Going back to the room, the door left ajar, I pushed it open and entered. To my shock, she had booked one of the sex suites, with a jungle d?cor and a king size bed. The room was darkened, lit only by about a dozen scented candles and an opaque scarf over the lights above the bed. Susan lay on the leopard bed cover with her ankles crossed with a very sensuous look on her face. Sliding off and standing up, she said, "There's the bathroom, get into your underwear and I'll help you with the rest." With a kiss on my cheek and a pinch on my rear, I grabbed my bag and proceeded to the changing room. With my mind spinning, I opened my bag. Starting from the bottom up I sat down and rolled up my French-cut pantyhose and slid them over one leg and then the next. Since the were new, they were tight and I had no trouble tucking my "clit" between my legs, giving me a female appearance and at the same time, feel safe that it was secure. Then came the waist cincher corset, which I have become very adept at putting on by myself. Straining the strings on the back, I pulled them extra tight and tied them off in the front. This gave me a very feminine 28" waist with 36" hips. Next the black bustier with the 34D breast inserts and black half- slip. I put on my wig and gave it a quick brush. Leaning over I inserted first my left then my right foot into the black satin heels. Not happy with the unfinished looked, I put on the sheer robe and was about to take an uncertain step and confront another person, for the first time, as Kristie. I was wondering how I felt having another person finish my look. Susan was sitting at a small round table, in front of the draped window, her legs crossed showing a lot of thigh and the top of her stockings. She had opened the bottle of wine and was sipping it as I appeared in the room. Stopping...I crossed one leg over another striking a very alluring pose. Looking at my tall, silhouetted female shape through the sheer robe, her mouth dropped. Putting down the wine, she rose, walked towards me and put her arms around my waist. She then moved closer until our bodies touched and looked up at me. At this point my arms went around her and we embraced in a gentle kiss. Our mouths opened and our tongues hungrily searched for each other. After a few seconds we both, simultaneously broke away and laughed. "You are making me hard!" she said. I came back with, "You...I was about to explode. Let's finish me up and go to the club." I grabbed my make-up bag and sat down at the small table. She moved the other chair opposite me and started her magic. First, with a small sponge she applied the foundation, insuring that any imperfections or black circles would disappear. Then she put on powder and blended it throughout my face and neck. The next step was the eyes. I had trimmed and plucked my eyebrows so they would give a highbrow look but could still pass as a mans. She then applied a combination of black and grey eye shadow. Then she asked where my eyeliner was, which I didn't have because I could never hold my hand steady long enough to put it on. She quickly got hers, made me close my eyes as she expertly put it on. Finally extra long lash mascara completed my eyes. Next she brushed a light blush on my cheekbones and around my chin. To complete the face, she took my ruby red lipstick, and with a brush, gave my lips a very seductive shape. She then went to work on the wig, brushing and teasing it to give it an evening style, finishing it with a little bit of extra hold hair spray. Looking at me with a very pleasing smile, she took my hand and bade me to get up and view her handiwork in the mirror. Walking over in great anticipation, I peered at myself and Kristie never looked so lovely. Just enough for an evening out but not too much to appear as a slut. A tear came to my eye as I turned and gave Susan a big hug and said, for the first time, "My name is Kristie." I opened one of the beers as Susan retrieved her wine and we toasted our newfound friendship and the evening of fun that was ahead of us. With that I returned to the bathroom and gathered up my dress and carefully put it on. Returning to the small table, I sat...crossed my silken legs and began to put on my jewelry, finishing with the large hoop earrings. Now the time for the final detail had arrived...the fingernails. Cautiously, taking them out of the container and placing them in order of size, with glue in hand I carefully started the process. When finished I extended my hand and admired the way it looked. Susan was over by the mirror, fixing her make-up when I walked up behind her and viewed my complete transformation. Asking her opinion, she said, "Kristie...you are a knock-out and the guys over there won't be able to take their eyes off of you!" With sprits of perfume in all the right spots, we grabbed our purses, put the necessary necessities inside and made our way to the door. As she opened the door I froze, since this was another step I had never taken. She assured me everything will be OK and lets go. It was 9PM and dusk was upon us so I took another deep breath and started the short walk to the car. Hearing the auto-locks disengage I quickened my step and opened the door. For some reason, instead of getting in my normal feet-first way, I smoothed my dress, sat and then swung in my legs. This brought a smile to Susan who quipped, "Kristie...tonight you have never ceased to amaze me!" It was a short drive to the club. Maybe, 15 minutes at the most. Upon arrival, we circled the main lot in front and found no spaces. Another packed Friday night. Unbeknownst to me there was another, very seldom used, transit lot on the other side of the tracks. Susan took the lead and drove around the corner and over the tracks, where we easily found a spot. Getting out of the car we started our walk to the club. We had to walk through a tunnel under the tracks that led to the rear entrance of the club. The sound of the clicking of our heels along the damp tunnel walkway heightened my excitement. At this point I realized that my ultimate dream was going to come true. Entering the club we walked to the desk to pay our cover. The cashier said, "Susan...you look lovely tonight, who is your beautiful friend?" "Kristie," she responded, "this is her first time here." With that he again welcomed us and waved us by, without paying the entrance fee. We proceeded, side by side, up the wide stairs and entered the area of no return. The music was blaring and once again the dance floor was hopping. Susan worked her way through the crowd, greeting the guys as she went. I got longing glances and acknowledgements that made me feel a little more at ease. She finally spotted her friends, this time they were not in the corner but sitting at the bar. As we walked up to greet them, Susan got the customary kiss on the cheek from all of them. I mostly got a puzzled look. One of the girls said, "Who's this long-legged stunner with you?" Susan quickly responded, "Joe...you remember Joe, he was here last week...we talked for a while then we both went off to get a drink." "Joe" they all seemed to screech at the same time. "Joe, is that really you?" another exclaimed. All excited they all got up and gathered around me, making me feel warmly welcomed into their little sorority. "Sit down," one of them said, "you are so tall and shapely you look like a model and make us look like everyday girls." I said no but they insisted that I sit, so I put my purse on the bar and with my best feminine manner I got on the barstool. Crossing my legs, my mini skirt rose to a dangerous height but with my pantyhose, I gave it no extra thought and enjoyed the feeling of showing of my legs to the world. We all ordered drinks and just girl talked. Clothes, shoes, make-up, romance movies or whatever came to mind. At first I just listened but as my confidence built I joined into the conversation. The DJ took a break and this allowed us to talk a little more lady-like without having to "yell." That 15 or 20 minutes set the tone for the rest of the evening. Kristie became one of the girls...a friend and trusted confident. We started planning an all girl party and for some reason I offered my home as the location. Since it was early June a 4th of July Party would be perfect. Susan became the party planner and would coordinate the whole event. The DJ started again and Susan said, "Let's dance!" Since I have only practiced dancing in heels in front of a mirror, I hesitated on my response. Then one of the girls said, "We'll all dance." With that one of them grabbed my hand and reluctantly I proceeded to the dance floor. This became the highlight of the evening...all of us out there at the same time dancing and having a ball. Guys would cut in, there was a lot of switching partners...it became the time of my life. The music then slowed and this 6'7" guy asked me to dance. I looked at Susan and she said, "Go ahead...this is what you're here for." I walked up to him and remembered to put my left hand on his shoulder and my right hand in his left. We danced, exchanged names and made small talk when he took my right hand and placed it around his neck while moving his hand to my waist. A strange feeling came across me as he pulled me closer and I could feel his body touching mine. As we danced around I spotted Susan with a big smile, when all of a sudden, she gave me the "thumbs-up." At that point I decided to enjoy the moment. I put my hand on the nape of his neck and held him tighter. Feeling his leg going between mine, I got excited and gave him look and a quick kiss on his lips. The music continued and we held each other even tighter. I put my cheek next to his. I could feel his hard-on pressing against my groin. I was also getting hard and I knew this could not go much further. The music stopped and we both went back to where we came. I was a woman and I turned away a man for reasons that I only know. Going back to the other girls I was greeted with applause. Then it hit me...I had to go to the bathroom. I leaned over to Susan and said, "I've got to pee...what do we do?" She said, "Go to the ladies room...silly, what do you think." With that she said, "Let's go...any one else have to powder their nose." Grabbing our purses we proceeded downstairs to the ladies room. Seeing the sign on the door I hesitated, but Susan urged me on, so I ventured into unknown territory. Walking in, the first thing I saw was a large lighted mirror with a long vanity and four sinks. To the right were about five stalls. Susan said with a laugh, "Don't forget to sit down, you are in the ladies room and don't forget to wipe yourself when you are finished peeing." She went into the stall next to me and we talked while we both pee'd. We both finished simultaneously and she said lets freshen up. We both pulled out our brushes and fixed our hair. Then a little more blush and finally the lipstick. Something that I never thought about became an overwhelming, memorable thrill. Back upstairs, we talked some more, drank a little, danced a bit and just enjoyed each others company. The evening was getting late and my feet were killing me. I could see Susan was also getting tired when she said, "Kristie...ready to go, I'm pooped." I quickly agreed and we said our goodbyes to the other girls and left for the evening. The drive back to the motel was quiet. Neither of us talked very much. I was anticipating what was going to happen next. Susan opened the door, kicked off her shoes and flopped on the bed. I quickly did the same and found my self lying next to her. We looked at each other and I caressed her cheek and thanked her for everything she had done. With that she rolled over, put her arm around me and gave me a kiss on the lips. This was not a gentle kiss as earlier but a deep, sensuous one that lasted forever. We both rolled together on the king size bed deeply attached. Our tongues ever darting into each other's mouths. We made out for about fifteen minutes when we both decided to get comfortable. I went back to the bathroom to disrobe. I took off everything. What a relief to get out of the corset. I stood in front of the mirror and washed my genital area when I noticed a container of "Wipe & Dipes" on the sink. Knowing what they are for I wiped my private area again... extra clean. I then put on my garter belt and bra. I opened the stockings, rolled them up into a doughnut and carefully pulled one then the other over my smooth legs. Standing up, I attached the four garters to the stockings. Then I pulled on the thong panties. Dropping the long, black gown of silky charmeuse over my head, I turned to the mirror and fixed my hair and make-up. Putting on my shoes and sheer robe, I went back to the bedroom where I saw Susan in a white gown, white stockings and matching white mules. She gave me a quick kiss and headed for her turn in the bathroom. As she passed me she said, "Get comfortable...I'll be right back...don't go anywhere." I lit the candles and turned off all the lights. I rolled back the bed covers, exposing the crisp, clean satin pink sheets and pillows. I then poured us two glasses of wine and placed them on each night table, propped up the pillows and got in bed and thought. Susan came out of the bath and got into bed next to me. We both took a sip of wine and started to recap the evening. We talked for a while when I touched her hand and held it while I rolled over and gave her a kiss. She quickly responded by putting her arms around me and returning my kiss. We then ran our hands all over each other's silky, smooth gowns, when she lowered her hand and started stroking my legs. A slight moan came from my lips as she moved her hand upward to the top of my stockings and the bare part of my upper thigh. At that point I squirmed, moaned and said, "Oh Susan...I love you." She continued stroking when she brushed her hand across my panties and touched my ever-increasing hard-on. Her hand remained right there as she rubbed me through my panties and got me very, very hard. At that point, she stood up and took off her gown. In full splendor with her white bustier and panties, garter belt and stockings, she reminded me of a bride on her wedding night. With that I also stood up, dropped my gown and stepped out of it. We then crawled back into bed and kissed deeply when she immediately again put her hand on my panties. Only this time, she pulled down my panties and released my beautiful, erect clit. Taking it in her hand she began to slowly massage it while kissing me tenderly on the lips and neck. Her kisses began to move down. Until she had my legs open and I was laying between them. She was on either side of my knees and my clit was right at her eye level. She reached out and touched it softly. I was moaning quietly with one hand on her shoulder and the other at the back of her neck, applying slight forward pressure. She continued to work her hand up and down on my shaft and then leaned forward and kissed the tip of my clit. She lifted her head, looked me in the eye and then licked her lips seductively. With her tongue she licked me up and down my shaft until I started to squirm with delight. My clit was screaming as she wrapped her mouth around it. I started to moan in enjoyment as she slowly worked it in and out of her mouth. She reached up and massaged my balls as she continued to lick and suck my cock. I became tense and my hips began to thrust. I warned her that I was going to cum. She quickened the pace while keeping her lips firmly wrapped around my clit. I shot my load that she enthusiastically swallowed. I felt my cock start to go soft, as her tongue licked it one last time. She then crawled up the bed with me. I looked at her, extended my arms toward her and gave her another deep kiss. We relaxed for a while, just spooning with each other and talking. When I said, "Susan' I want you to take my virginity. I have thought about this for years. Will you please make love to me?" She said, "Yes," and kissed me deeply. With that she leaned over and opened the drawer of the nightstand. Looking me in the eye she showed me a rubber and a jar of anal lube. She opened the rubber and placed it on her erect clit. She then rolled me over, opened the anal lube, and generously put it around my sphincter and the rubber. She moved her finger around my sphincter, ever so slowly applying pressure at the point of entry. She then put her finger inside me to ensure the anal lube would do its job. I moaned and said, "Yes...Yes...Yes!" I then got up on all fours, looked back over my shoulder, with a tear in my eye, and said, "Susan, I will remember this night for the rest of my life. You've made me so happy" Susan got behind me, pulled down my panties and began to spread my legs to allow her easier access. I felt her clit at the opening of my ass as she began to apply pressure. At first it hurt slightly and I asked her to be gentle. As she continued to apply pressure, she said, "Sweetheart, I'll never hurt you...never!" I felt the head of her clit pass by my sphincter. As I let out a loud moan she stopped to give me time to get used to the feeling. After a couple of minutes I pushed back slowly on her and felt her clit slide deeper into my ass. I continued to thrust until I could feel her hips against my ass. I was completely relaxed with Susan all the way in me...the feeling was sensational. She moved her hand to fondle my tits to as she kept on fucking my buttocks. She started to go faster and I increased my hip movements to keep up the pace. She began moaning, first softly and then louder, as she shot her load into my ass. Once again we moved to a spoon position only this time her clit never lost touch with my ass. We kissed and fondled each other until we both fell asleep. When I awoke, seeing Susan lying beside me, I remembered our wonderful evening the night before. I grabbed my gown and panties and went to the bathroom to clean myself inside and out. I fixed my makeup and hair and quietly went back to the bed. I brought a warm washcloth with me and began to clean her erect, morning clit as she slept. I then took it into my mouth and began to lightly lick and suck it. I looked up and saw that she was watching, as I said with a smile, "I thought this was for me." Susan then went to the bathroom. When she came back she was wearing a blue charmeuse and matching lace baby doll. Giving me a deep, tender kiss while rubbing my clit, she said, "Kristie...I want you to make love to me." With that she rolled over. Taking my clit in my hand I guided it toward her treasure trove. Slowly I applied pressure until it broke through into her dark secret. I began to thrust, gently at first until she completely relaxed. As she began to return my thrusts I started to increase the momentum. I was all the way in her and she was screaming with delight. She was rubbing her clit while I was fucking her ass. Our moans became louder as we were both on the verge of a massive explosion. As my thrusts became supersonic and my legs tensed, I knew my orgasm was going to be enormous. I came in her ass while she shot her load all over the bed covers. We had both had cum at the same time as we fell apart in complete exhaustion. Lying on our backs while catching our breaths we started to talk about when we could see each other again. Susan had an upcoming business trip that was going to take her out of town for about ten days. With that we both got out of bed and packed to prepare to leave. We cleaned off our make-up and took off all of our female finery. We both kept our panties on as we dressed in our "Joe" and "Tom" clothes. Looking like very ordinary guys we shook hands and left the room. We both drove off in different directions. In thinking back, I will always have fond memories of the first time with Susan. Her taking me under her wing and showing me my true feminine side. For that I will never forget her. Over a lifetime it is hard to find friends as great as that...