Date: Tue, 3 May 2005 17:14:08 EDT From: TexLee29@aol.com Subject: still the best! I'm Lana Lee, a bisexual crossdresser living in Dallas, Texas. I started dressing at 13, had sex with a man at 17, and am what you might call a crossdressing slut now at 21. I really love dressing up all sexy and pleasuring a man with my red lipsticked lips and tight little ass-pussy! I used to dress up and masturbate until at 17 I had sex with a great guy and I was hooked. Although I still masturbate a lot, nothing compares to a real live hard cock! I thought today you might like to hear the story of my very first real fucking... Since my dad moved out when I was young I lived with my mom in a nice house in the Dallas `burbs. Mom had a weeks vacation planned with her boyfriend in Las Vegas so naturally I was so excited to have the house all to myself to dress up for the entire week! By now I was buying all my own make-up and clothes so I spent several days in advance of her leaving by shopping for some great sexy clothes, and make-up...I just love playing with make-up and prancing around in super high heels! Just minutes after she left the house I, poured a glass of wine and stripped naked except for a pair of red thong panties and my red high heel pumps. The wine and the panties and heels gave me a nice warm and fuzzy feeling and I headed to my computer for some trash talk in one of my favorite crossdressing rooms. I love flirting and teasing the boys online and it always gets me soooo incredibly horny. Never did I intend to hook up with anyone. I played online for a guess an hour or so then got an instant message from a screen name of Sexy Sam. Sam noticed my picture in my profile and said he thought I was very sexy and he wanted to talk to me. After the usual small talk he invited me to watch him on his web cam and I naturally accepted. What a specimen! Sam was 37 (married) and a tall, well built black man with a beautiful and well endowed cock! I was mesmerized watching him stroke it while we talked dirty to each other. Keep in mind I was still a "virgin" at this point but I told him I was 21 and experienced so between the wine and my hornies, I agreed to meet him for some fun. We decided he should come over to my place that evening around 7:00. Wow, was I excited! And extremely nervous too! I always felt so confident when I dressed alone, but to be dressed in front of someone else I felt so much pressure! Since it was only 2:00 in the afternoon I decided to lay out all my clothes and make up in order to dress to impress my first boy-toy. I was so nervous I took one of moms "happy" pills, relaxed on the couch and watched a porn flick, paying special attention to the blow job techniques in the movie. I will never forget how excited I was, knowing what was about to happen that evening!! At about 4:30 I floated over to the bathroom for a long hot shower. I don't have much body hair but I shaved under my arms and trimmed my pubes nice and short. I dried off and powered myself with a scented powder, squirted some baby oil into my pussy ass, (and of course had to finger myself while I was there!), and sat down at the vanity. As I said I love to play with make-up and since today was the big day, I decided I must have the slut/whore look for my new man. I used a light beige foundation and several shades of blue, silver, and purple eye shadow, extra long false lashes and several coats of black mascara, and eyeliner. I outlined my lips just over their natural line with a dark brick red lip pencil and filled in my now full lips with a creamy Chanel called Velvet, and a dab of Mac clear gloss. Whew! It looked so hot! Next I decided I needed a glass of wine to settle my nerves a bit so I slipped into a black lace bra (and silicone boobies) and matching boy shorts with my hard cock poking out the side and headed to the kitchen. I poured a glass and took a sip admiring the sexy lipstick print on the glass. I felt so privileged to be a boy and be able to experience the wonderful and heady feeling of extreme femininity! And my first date as a girl is on his way over! I headed back to my bedroom and slid on my black fence-net "hooker" stockings, then my black 5" pumps. I am 5'8" tall, but in those sexy pumps I am a towering 6'1". Fortunately Sam said he was 6'4". Since Sam said he liked my profile picture and I was wearing a long blonde wig in the photo, I selected the same to wear for him. The wig is full, teased, and shoulder length with several shades of blonde streaked through it. Fortunately it was a good hair day! I decided on my black tight miniskirt that showed my stocking tops and a red shear see-thru blouse with gold necklace and dangly gold loop earrings. Lastly I applied a set of long red glue on nails. Gawd, I look good enough to fuck! I put my lipstick, gloss, powder, and two rubbers in my purse and headed back to the kitchen to retrieve my wine glass. My heels made that sexy clicking sound across the tile floor of the kitchen and I noticed it was already about ten minutes to seven. I refilled my wine (and another "happy" pill to calm down and retouched my lipstick in the hall mirror just as the doorbell rang. My heart about leaped out of my chest and I was instantly torn between regretting I set up this date and raping the poor guy on the foyer floor! I looked thru the peep hole and there he was. Looking great with a bottle of wine and some flowers! I called out, "Is that you Sam?" and "Yes it is baby" was the reply. I opened the door and Sam just stood there staring with his eyes wide open. "Holey-moley" he said, "You look fan-fucking-tastic". "Why than you Sam", I blushed. He stepped in and wrapped his huge arms around me and squeezed me tight, causing me to loose my breath, and he kissed my neck. We parted slightly and looked into each others eyes and I swear I felt my knees buckle! "Come on in and make yourself comfortable Sam" I said, finally breaking the spell. Sam handed me the wine and presented me with the beautiful flowers. "My very first flowers", I said, forgetting I told him I was 21 and experienced. "I can't believe someone as sexy as you never got flowers before" he said. I told Sam to have a seat in the living room and I would pour us a glass of wine. My pill kicked in when I was in the kitchen and I felt absolutely wonderful! I seemed to be walking on air which is not easy to do in 5" high heels! As I walked toward living room I heard the porn tape playing and was so embarrassed. I'm sorry, I didn't mean to have that on" I said as I searched for the remote to turn it off. "No, no, leave it on Lana, its good for me", said Sam. "OK, if you say so" I sheepishly replied. I handed Sam his wine glass and stumbled a bit as I sat down. "Looks like I have some catching up to do", said Sam as he raised his glass to his lips. He gulped it down in two or three big sips. I offered to get him another but he got up first and headed to the kitchen, returning with the bottle in hand. "So, Lana, you look fantastic and I am real glad you invited me over tonight", he said. "Me too, honey" I said and scooted over next to him on the couch. "My Gawd, look at that, a black guy getting head from a white chick" he said looking at the TV. "Mmmm, that's my favorite part of the movie" I purred. Sam put his big arm around me and squeezed me tight almost spilling my wine. We laughed about it and talked for a while, just getting to know each other. Sam works as a lineman for the phone company, is married with two kids and only lives about five miles from me. He said he is bi but only with She Males, trannies, and Xdressers. He especially likes blonde, white chicks. (Lucky me!) It was obvious Sam liked what he saw because he had a huge bulge in his jeans. I wanted to rub it so badly but I guess I was a little shy or maybe it was my lack of experience. We snuggled there on the couch for a while longer sipping our wine, talking and watching the porn movie. I felt pretty buzzed by now, and totally into the moment. Nothing else existed and I was prepared to let Sam use me for his wonton pleasure. Just as the black guy in the movie was about to shoot his load into the white chicks mouth, Sam said, "That looks like it would feel so great". "Oh yea" it sure does", I replied. I hesitated for a second or two then reached for his zipper and pulled it down. My heart was racing as I reached in and wrapped my hand around his big hard cock. My very first cock! No underwear, nice touch I thought! I tried pulling it out but the big boy wouldn't fit through the zipper opening. I was obviously fumbling and I certainly didn't want to hurt him so I withdrew my hand. "Tell ya what honey, I'm going to go pee, so you get yourself comfortable and I'll be right back". I said. "OK, baby", he said, I will be ready for you when you get back". Sam stood up first and took my hand to steady me. (Wine, "happy" pills, and 5" high heels, you know.) He grabbed me tight and surprised me with a long wet tongue kiss, and I about melted in his arms. Gawd was he sexy! I finally excused myself and made it to the bathroom. I looked in the mirror and other than glossy and unfocused eyes and smeared lipstick I looked pretty fucking great. I tried to pee but my hard "clitty" didn't seem to want to cooperate, so I stuffed it back in my boy shorts as best I could and pulled up my stockings. Back to the mirror I wiped off my smeared lipstick, dabbed on a bit more foundation and reapplied several creamy coats of lipstick and a bit of gloss. I bit more blush to my cheeks, and a squirt of perfume behind my ears and I stood back to admire my reflection. I really looked so damn fuckable! I can't even describe how fantastic I felt inside. So incredibly horny and butterflies in my stomach knowing there is a great looking guy with a huge cock waiting my return! I returned to the living room and smiled at Sam. He had removed his pants and shirt exposing his toned body with his penis stick straight up in the air. I would guess it was around 8+ inches long and his balls were enormous too. I slid over the coffee table and knelt down between his legs, and looked up at him. "I sure am glad you came over Sam" I purred. "Oh baby me too, you are so fucking hot" he replied. I wrapped my hand around his cock and couldn't help but notice how great my white hands with long red fingernails looked around Sam's big black hard black tool. I felt so strongly drawn to suck on it but I resisted and planted several soft kisses on its now pulsing head, leaving my lipstick prints on it. "Oh baby, suck me" he whispered. "Mmmm" I moaned as I parted my lips and wrapped them around its head. I held that position as I flicked the head with my tongue. "Ah, yess, that's it", he hissed. Slowly I begin bobbing my head up and down on his cock, going a little deeper each time, until the tip of his cock reached the back of my throat. With my very first cock in my mouth I remember thinking how different it was than the dildo I practiced with. It was both hard on the inside, yet soft and warm on the outside. "Oh baby you sure can suck cock" he said, making me feel so feminine and sexy. I alternated between sucking and licking his long shaft and swollen balls, and wished this could go on forever! The sound of Sams moans mixed in with the sounds of the porn on the TV and I was in a cock trance (as I now call it) and lost all track of time. The hell with the rubber, I wanted Sams cum in my mouth so bad! Sam was breathing real heavy and I remember wondering if I would get any signs he was going to shoot, when I felt Sams cock head bulge then his body stiffen. "Don't stop baby I'm cumming, yes, yes, yes" I picked up my pace bobbing up and down as deep as I could take it, then it happened... First I tasted slippery pre-cum. Then a small squirt and a musky, salty taste in my mouth, then Sam unloaded several big squirts into my mouth. My head was spinning and I swallowed as best I could but it was even too much for this little slut to handle and it ran gown my chin. Sam relaxed as I licked his cock clean and used my finger to wipe my chin and suck it off my finger. "Gawd baby that was fucking great" he said with a laugh. "It was great for me too hon!" I said, savoring the taste of cum for the first time. Sam was panting as I got up and sat down next to him on the couch. "It's still hard!" I cooed. "It does that sometimes baby" he said between pants. "I'll be right back, I said, and headed to the bathroom. In the bathroom I looked in the mirror and smiled back at myself. My first blow job and it was even better than I expected! I powered my face, reapplied my lipstick and and headed back to Sam for more. Sam was still sprawled on the couch as I grabbed our wine glasses and headed to the kitchen to refill them. My buzz was mostly gone having been replaced by my satisfaction of giving a great blow job. I returned to the living room as Sam sat up to accept the wine. We snuggled together, Sam completely naked and me fully dressed as we sipped down our wine and talked, as Sam stroked my stockings. "Are you ready for more hon?" I eagerly asked. "Always baby" he replied. I stood up and held out my hand for Sam then grabbed him by his still hard dick and he put his hand on my ass as lead him to the bedroom. I led him to the bed and he lay on his back and I sat next to him massaging his cock. "What can I do for you know honey", I said. "You can give me some of that tight ass of yours, baby" he said. "My pleasure sweetie" I replied. I stood up and unzipped my miniskirt and wiggled it over my ass and down to the floor and stepped out of it and then I unbuttoned my blouse and removed it, and took off my boy shorts, leaving on my bra, stockings, and high heels. My hard "clitty" was exposed and at attention and Sam leaned over and took it in his mouth. It felt like my clit was wrapped in velvet as he expertly sucked me. "That's not what you are here for honey" I said as I reluctantly pulled away. I reached into the night stand for some baby oil and poured some into my fingers and reached under to lubricate my ass. I then poured some into my palm and reached for Sam's cock, getting it all nice and slippery. I climbed on top of him straddling his body with his cock between my ass cheeks and bent down to kiss him. As my lipstick smeared all over his lips we locked in a deep tongue kiss that seemed to last forever. I then reached around and guided his dick to my love hole. I read I was supposed to push out my sphincter muscle like I was pooping so I did so as Sam slipped right in! Gawd, it felt so incredibly full! I gyrated my ass in little circles as Sam moaned. It slipped out a few times but my ass pussy seemed to suck it back in for more. "Let me have that ass from behind Lana" he said, so I dismounted, got on all fours and put my ass up in the air inviting Sam to mount me. Sam squirted some more baby oil into my crack and I felt it run down to my awaiting hole. "Don't hurt me honey", I said. "Don't worry baby, I wont" I felt Sam's cock slide up and down my crack a few times the he pointed the head at the opening. I pushed back, and deep inside it went with no resistance at all. After a few long slow strokes, Sam (and I) picked up the pace. Soon he was fucking fast and hard. "Do me honey, fuck that slutty ass" I panted. "I'm fucking that ass you whore cunt" he panted back. "Cum in me, please cum in my ass honey" "Yes, baby, I'm ccccccumminnnnnnnng" Wow, now that was something! We lay there for a few minutes catching our breath. I looked over at Sam and he had a big smile on his face. "Guess you liked that, huh Sam?" "Ohhhh yesssss, that was perfect baby" I got off the bed on my now rubber legs and slipped my boy shorts back up just as a big glob of Sam's cum oozed from my ass. I decided to leave it there and enjoy the gooey feeling between my legs. (So much for rubbers, huh?) Sam stood up and kissed me deeply and dropped to his knees, pulled down my boy shorts and again took a "clitty" in his mouth. It only took a few minutes when I felt it build in my toes, up thru my legs and into my clit. I came hard in Sam's mouth. Sam stood up, and we kissed again, and I was surprised Sam didn't swallow my cum, but slid it into my mouth with his probing tongue. By now I looked like I just got fucked buy the entire US Navy, so I retreated to the bathroom to try to repair the damage. Sam joined me and sat down to pee as we talked. (Guess we were now fuck buddies, so peeing in front of each other is OK). "Is it OK if I take a shower?" he said. "Only if you let me watch" I cooed, and we both laughed....