First Time Out - Ending 2 free porn video

First Time Out - Ending 2 By: Rachael Free I had dressed all my life but finally got the courage to go out as a girl. How I started and the progress over the years is typical of other girls. You may even think I'm writing about you at times. The fateful day was approaching to come out as I planned the evening for months. My wife went away for the weekend and I would be in heaven becoming Trina. The series of events broadened my experiences but sadly also changed my life forever. If only my wife could have helped, none of this would have happened. zzzzzzzzzzzzzzzzzzz My story begins when I started frequenting all the wonderful TV, shemale and crossdresser sites on the internet. Hi, my name is Jason. Just like all the other girls, it was a new experience for me. Many other girls have had the same things happen to them, grew up dressing in their mothers clothes and their sisters clothes. They may or may not have been caught dressing but for the most part have kept their secret hidden for years. In my case, it was over 40 years of being Trina. The internet has brought so many opportunities, so many places to buy things and so many wonderful girlfriends online. The relationships on-line have given me more confidence in who I am and who I want to be. Of course my wife has no idea that I even dress up. Sure I've tried some games in the bedroom with her with me wearing her pantyhose to bed or wearing a pair of her panties but she would get turned off and push me away. I'm not a big guy and not very built. In fact my wife and I are about the same size. She's sort of big for a real girl at 5'10". She's only 135 pounds while I'm 156 soaking wet. Growing up was easy because my sister and I were twins and grew up at the same rate. My first experience with dressing was when she would play tea party and I would have to wear one of her party dresses. We were very young and my mom didn't really care as long as we got along. Dad was always at work so he didn't even know. My obsession with girl's clothes didn't wane. Our dress up parties faded away but my need to dress just got stronger. I would sneak a pair of her panties from the hamper and put them on when I went to bed. I even went further taking pantyhose, bras, and even slips for my evening escapades. No one ever complained or challenged me. They had to have known. I accumulated over three full sets of fancy under things over a two year period. Maybe she didn't notice because we both were growing and she needed larger bras and stuff. By the time I was 15, I knew everything about women's lingerie, foundations, makeup, shoes, and even clothes. My sister and I would go shopping and she would always buy the trendiest clothes. I would ask all sorts of questions about styles and fabrics and she just blew them off thinking I was interested in how she looked. I was truly interested because I wanted to dress the same way. My dressing continued throughout this period and I loved trying on her newest fashions when she was out and Mom went shopping. There were, of course, a few close calls with either Janey or Mom coming home early but I had developed an elaborate practice of covering my tracks and being able to change back in less than a minute. My hiding places for my accumulated fashions were truly hidden from anyone too. This went on until I went to college. I realized with me being out of the house, someone may find my things and I would have real trouble. I purged everything except for my small stash of makeup, a frilly bra and panty set and a pair of 4 inch heels. My hiding spot could never be found so I felt comfortable that at least I saved something from the past. College flew by and my dressing was reduced to visits home and nightly dressing sessions. I was about the same size as my mom and could nab a dress, or a blouse and skirt and put it back the next day without any attention. Janey had gone to the west coast taking most of her things and I only saw her on holiday for the four years away. We always talked and wrote each other but I knew my dependence on my sisters things were over. Forward a few years............. After college I moved away for my first job. Mom and Dad didn't have too much heartburn because I was only two hours from home and both Janey and I had been away at college anyway. My dressing was really non-existent with me sharing an apartment with a co-worker. I did enjoy the magazines with crossdressing tales and other magazines with pictures of shemales and transvestites. That seemed to keep me secure without dressing up. Manual relief always accompanied my magazine sessions. I met a girl when I was 30 and we fell in love. The courtship lasted over two years. We moved in together the second year and I was completely surrounded by her feminine finery every day. I would try on her panties or a bra or even a dress or skirt when she was shopping or at church or out with the girls but that was about it. Her clothes fit me perfect so I didn't have to buy anything for myself. This stopped though when she complained the waistband on one of her elastic skirt was stretched out. My gut was a little larger than my wife, Melissa's and I guess I did stretch t out over time. I inspected the garment and told her it was just the elastic wearing down. The skirt was over five years old. How did she ever expect it to stay the same after all that time. She believed my story and never discussed it again. Our life grew together and we were deeply in love. My dressing was hit or miss up until the time I retired. Melissa had a great job with the Government and I retired early from my company. This gave me time at home to engage in my hobbies, help with the cleaning and dinner and basically become the house husband. Melissa was gone from 7AM until 6PM leaving me alone five days a week. After a few months I lost interest in my hobbies and lazed around the house more and more. Melissa started complaining about my bad habits and I made a concerted effort to provide her the best home anyone could ever live in. We still loved each other and quite frankly, doing nothing was even more boring than anything. I got into a routine of cleaning all the bathrooms Monday, dusting and waxing on Tuesday, vacuuming everything and doing wash on Wednesday, Mopping and cleaning the kitchen, pantry and laundry room on Thursday and preparing the house for a fine dinner every Friday. Saturday and Sunday found me serving her breakfast in bed and doing whatever she wanted to do that day. Most Saturdays were spent shopping in the women's section of the store. I would browse the aisles while she would choose clothes and try them on. I would fantasize about a particular office suit or a frilly dress or a skirt and blouse set while I browsed myself. She would comment on how she liked me shopping with her and that she didn't feel any pressure to finish. Of course she didn't know I loved it too. Too bad I couldn't pick something out and try it for myself. Our life went on in a normal routine. I found I could get my work done by 11AM and then sit down and watch Jerry. The shows with transvestites, shemales and transsexuals were my favorite and I would always know which days these were playing so I could be done with my work on time. My cleaning became routine and the house looked great. One Wednesday I was doing the laundry when I found a sexy pair of white, silk panties and matching bra. Melissa looked great in it with her cream Sunday dress. I held them in my hand and enjoyed the silky material. Without thinking, I dropped my sweat pant and took of my tee shirt and put on the bra and panties. The cups were filled with a few socks and I rummaged through the laundry basket to see if she had put anything else of her in the basket. Well, Melissa had worn a see through blouse and tight black pencil skirt the day before and it was in the wash. My heart was pounding as I slipped my arms into the blouse and buttoned it up. You could see the outline of the bra through the material. The skirt slid up my legs and I zipped up the back. The fit was perfect. My fake titties filled out the blouse perfectly and I spent the next two hours doing more cleaning while I wore her clothes. The clothes caressed my body and I felt so girly doing the chores. It was a turn on for me remembering my past and how good I felt wearing women's clothes. I was interrupted by the front doorbell and hid in the bathroom. After a few minutes I ventured out and looked out the window. A UPS guy just dropped off a package. That was really close, for sure. Melissa was due home in a few hours so I undressed, put her things back in the hamper and started dinner as if nothing had happened. We ate dinner and Melissa commented on how nice the place looked. I felt proud of the work I had done and thanked her. She went to change and dropped her things in the hamper. She came out and said, "I thought Wednesday was laundry day?" My mind went blank then I spurted out, "I got caught up in a movie and didn't get to it dear. I'll do the laundry tomorrow." She just said OK and let it go. Wow, I would have to do a better job covering my tracks next time. The next few weeks gave me an opportunity to try on more of her things, get dressed further with pantyhose, heels and a wig she had in the back of her closet. I would be showered and shaved every morning before she left and within the hour I became Trina. We lived in the country so we didn't get many unexpected guests. My courage increased and I would wear her jeans or a pair of slacks with a nice blouse to hang the laundry on the line. A skirt would be pushing the envelope a bit. Inside I always wore a dress or skirt. Pants wouldn't do for Trina. The house remained immaculate and I would have everything in place before Melissa would come home. My dressing even expanded to wearing makeup, earrings and jewelry as I flitted around the house doing chores. Voice practice helped me raise the octaves giving me a breathy, feminine quality to my voice. I got so used to being Trina that I would have to remember being Jason when Melissa came home and lower my voice. My little alter ego went on for quite some time before I felt something was missing. Melissa would go beserk if I brought up my new hobby to her but I was also getting settled in being Trina and losing the spark that accompanied me dressing up. The routine was the problem. I needed some other type of outlet. We bought a computer and I would surf the net for hours after I cleaned the house. The TV, transsexual, crossdresser sights caught my eye and I then was obsessed with going on line every day to see new girls, chat with others and get off watching movies and looking at pictures. I would dress quickly in the morning, do my chores very fast and then spend most of the day surfing. It was a new thrill that seemed to satisfy me for now. Purchasing some things I needed for Trina was easy and I now had all the basics for myself including hip pads, breast forms, bras, gaffs, corsets and all sorts of other things. Trina was getting to be a hottie as I perfected my look. I made quite a few friendships with other girls and took the plunge. I put some pictures on the sights and wow did I get even more responses. It took every minute I had to respond and check all my sites. My mannerisms while doing chores and being Trina on line made it difficult for me to break away at night when Melissa came home. She even commented that I was becoming more distant. One day she commented on how I was crossing my legs when we watched a movie. I played it off that I had lost weight and my legs just felts more comfortable. She shrugged her shoulders and I ignored the comment. I'm glad she didn't look too close at my perfectly manicured finger and toe nails with the clear coat of polish I would apply during the day. One Tuesday, I was chatting with a girlfriend when I got an Instant Message. It was from a girl close to me who wanted to meet me. I had never gone out in public except for my forays in the back yard. We chatted for a few weeks and she kept urging me to set some time away so we could meet. I paid more attention to Melissa during this time so I wouldn't cause her to suspect anything. My girlfriend, Belinda, kept asking me and even recommended she would pay for a room for us. I didn't want to say no but I was very intrigued. Belinda was a pre-op and had beautiful breasts. I had always fantasized about pre-ops and chatting with her turned me on. I would find my panties soaked with my cum after our chats. This would turn me on and sex with Melissa would be great that night with me closing my eyes and being Trina. Melissa had planned on going to her mothers during Easter. I told her I wanted to work on the outside that weekend and she could go alone. Without giving it any though, she agreed and the free weekend could be planned. I had two months to make sure everything was covered. Belinda and I would still chat and set our rendezvous. The weekend came and Melissa left after work on Friday night. I spent the entire day primping myself. A long bubble bath prepared my skin. After drying I realized I needed to remove some of my face, chest hair and underarm hair. I had few chest hairs so that was easy. I didn't think Melissa would even notice my underarms so I shaved off all the hair. I felt so cool and weird without the hair. Some Secret underarm deodorant gave me a feminine smell. My legs were sparse with hair so I figured pantyhose would cover the hair enough for the weekend. The scented lotions in Melissa's room made me feel soft and pretty. I used her moisturizing lotions in her makeup drawer and loved the silky feel of my skin. Just a light coat of foundation for today so I wouldn't be noticed when I drove over to our rendezvous. Packing some things was one of the toughest things I did that day. Should I be a sexy vixen, or a straight laced secretary? I couldn't decide so I packed about five sets of clothes with matching lingerie. I know it was only for one night or maybe two but I wanted it to be special. I chose a pair of jeans and mans shirt for the drive in case I was stopped for any reason. No wig for the trip either. We decided to meet at a coffee shop next to the hotel so we could go in together. Belinda was living as a girl 24/7 and passed easily. I didn't believe I could pass so being a guy worked out the best. I walked into the coffee shop and immediately saw Belinda sitting at a table. She looked great in a vee neck top showing off her boobs, a nice short skirt, silky legs with 5" heels and perfectly made up. She was smoking a long feminine cigarette and her long, polished fingers turned me on. I introduced myself, shook her hand and took a seat. She told me to relax. We looked like any other couple in the room. I began to relax as we chatted about ourselves. Belinda lost her parents when she was young and moved from household to household until she was eighteen. She was exposed to all sorts of terrible situations and found herself becoming Belinda to escape from the reality. As she grew older, Belinda became her life and she decided to pursue changing into Belinda permanently. Her story made me feel bad for her but she told me that she was never more grounded. We chatted for another hour and she suggested we go to our room. Belinda had already checked in. She reserved a suite with a fireplace and Jacuzzi tub. This room was great and the company even seemed greater. Belinda had brought some wine and snacks and I poured us two glasses. We clinked and sipped our wine. Belinda reached for my glass and set it down. She wrapped her arms around me and laid a big kiss on my lips. Her lips were soft, puffy and oh so tasty. I responded with me wrapping my arms around her and pulling her in closer. Our lips meshed together and our tongues played with each other not wanting to be too aggressive. Our kiss ended and Belinda told me to undress. My entire body was trembling with excitement as I went into the bedroom with Belinda following. My clothes were off in a matter of second as I stood there in my gaff, panties and pantyhose. My red polished toenails were obvious under my stockinged feet. Belinda slid her hand up and down my legs cooing in my ear. I opened my bag and proceeded to lay out my clothes. Belinda hung up my suits, blouses, dresses and skirts as unpacked my silky lingerie. She held a few things up and complimented me on my tastes. My face got warm and I was blushing. She had me lay on the bed as she helped attach the breast forms to my chest. I usually just put them in the bra cups but she insisted that I feel like a woman, not just look like one. She took out some cream and worked on blending in the seams. She did a great job and unless you looked directly at the seams, no one would ever notice they weren't real. I then put on a molded goddess bra and adjusted the cups over my breast forms. She laughed saying the bra wasn't fitted correctly and should fit better now. It was true. It didn't seem to pinch me under my arms and I felt much better. Belinda had me sit down and she took her makeup and went to work. She sat on my lap at times, facing me as she would use all sorts of things I never used on my face. She even put a pair of false eyelashes on me. That was a first for me. I looked in the mirror and didn't recognize myself. Even without a wig you wouldn't know it was me. I reached for the wig and she slapped my hand lightly. I have one that will work perfect for you my dear. She opened a case and a beautiful mid back length blonde wig emerged from its cradle. She flipped some hair away as she placed it on my head. She put a few drops of liquid near my ear, my forehead, the back of my neck and on my temple as she held it in place. Once she felt it had set, she fluffed it with a fork and told me to stand up. She looked through my clothes and selected one of my little black dresses. It had a plunging neckline and was six inches above my knee. I put it on and she saw it was a little tight so I removed it and she had me step into a cincher. I had used one before but liked a front laced corset the best. She pulled the cincher up and under my bra and then laced me up, pulling in certain areas to give me some more form. I stepped back into the dress and the zipper just slid up. The dress wasn't tight and hugged my new curves. I felt wonderful too. She selected some clip on earrings, a necklace and matching bracelet and a few fake diamond rings. I brought three pairs of heels and of course she chose the highest. They were black patent leather with 5 inch heels. Perfume was sprayed into my cleavage, behind my ears and on my wrists. The scent was intoxicating. Belinda then had me look at the final deal and what I saw staring back took my breath away. I had never been able to accomplish anything like this. I was stunning and looked like a real girl. Belinda had me sit and finish polishing my longish manicured nails in deep red while she fixed herself up. The polish made my fingers look sleek and slender and let them dry. Alternate Ending 2 I was told to go wait in the living area of the suite while Belinda finished dressing. Standing up and swishing my way into the living area, my heart pounded from the feelings of being a woman. The couch beckoned me as I smoothed my dress and sat as feminine as I could, crossing my legs and showing off my sleek legs. I turned on the TV and found a cable station with porn movies. As the movie played I found myself rubbing my tits (even though they were fake). The movie was turning me on as I sat and watched guys fucking girls and girls fucking other girls. I'm glad I put on a panty liner so I didn't leak out onto my pretty dress. Belinda opened the door and stood there dressed in a leather cat suit outfit from top to bottom. Her body was beautiful and her tits filled in the suit like a glove. She had 6 inch jet black heels on and black leather gloves with a black, short whip in her hand. She called me over to her with her finger. This was getting excited. I had always wished for my wife to do something like this but never thought it would actually happen. Standing very gracefully, I wiggled my ass as I walked over to her trying to be as sexy as I could. She pushed me down to the floor in front of her and released her big, thick cock. This was the first time I had ever been this close to another cock and here was one, hard as ever with pre-cum dripping from the tip. Belinda stroked the back of my head with the whip and urged me closer to her. My mind said no but Trina liked it. My mouth instinctively opened as my tongue licked her tip and cleaned off the cum oozing from it. I looked up at her and licked my lips as she smiled back at me. My hands reached out and took her cock, seeing my neatly polished finger wrap around the base. I got a tickle as Trina took over inside my head. My tongue licked the shaft up and down and even sucked on her shaven balls. Working my way back up the shaft my mouth opened and took her bulbous head in my mouth. Slowly I lowered my head down and took her deep in my waiting orifice. My hand was stroking her base as I bobbed up and down on her thick tool. I could hear her moaning as I sucked her like I always wanted my wife to do but never had the chance. My eyes were closed as I kept up sucking her off. Finally, Belinda reached the back of my head and pulled it down to her groin. Her cock twitched as I felt a flow of warm fluid hit the back of my throat. I had to swallow hard as another load hit me. She let out another load and then her rhythm slowed. I could feel her tool still erect in my mouth as I gulped down the cum in my mouth. I kept sucking on her hard cock and licked up a few drops of her juice that were left. My own cock had tried to respond but it was held in tight with the gaff. I need to relieve myself and wished Belinda would take care of me like I serviced her. Belinda then ordered me to bow down on the floor on all fours with my ass in the air. I felt her come around behind me and raise the hem of my dress. She then pulled down my pantyhose, panties and gaff, exposing my virgin ass. Belinda told me to just relax as I could feel her drip some liquid on the crack of my ass as she worked the cool liquid into my crack and around my anus. This was getting hotter by the minute as her lubricated finger entered my ass. She would finger me and then add some more lubricant making sure I was well lubed. She pushed two fingers in and then three, working my asshole so I could take al of her. I knew what was coming but was surprised when I felt a vibrating tool enter my waiting ass. She had a vibrating toy and was fucking me with the tool. I had played with a few myself when I was dressed but she worked the vibrator like a pro, knowing exactly where to stop and what part of me to tickle. She fucked me with the toy for the next ten minutes as she pulled out the toy and positioned herself directly behind me. Her hard cock pressed against my waiting hole and she pushed her cock deep into my very wet, lubed ass. The feeling of her hard cock was incredible. I thought I would hurt but instead, after all the work with her fingers and vibrator, her cock seemed to fill the need. She rammed her tool deep into my ass and fucked me for all I was worth. She told me to scream and tell her I was her bitch. I was more than just her bitch, I was her fuck toy. I yelled out, "Deeper, deeper, please fuck me deeper." Her thrusts quickened and I responded by meeting her thrusts with my own. Pictures couldn't tell the wonderful fulfillment I was feeling at this moment. The more she pushed, the more I responded and moaned in pleasure. Her cock got thicker as she stopped pushing and held my ass close to her groin. She erupted in my ass as a wave of warmth enveloped me. My own cock was released from its tight prison and was hard as a rock. Belinda pushed against me again and another warm load entered my virgin pussy. She slowed her thrusts as her cock began to soften. I felt her pull away as her cock slipped out of my ass. She cam over in front of me and told me to clean her off as I got on my hands and took her slimy cock into my mouth, licking off her cum and all the other juices until she was clean. I could feel her cum leaking out of my ass when she came up to me with a tampon and inserted it in my ass. It tickled as she withdrew the sleeve leaving the tampon and sting in my now defrocked pussy. I'm glad I brought the tampons with me now. The tampon swelled up absorbing the fluids inside of me. She told me to pull up my panties and hose and straighten myself. My butt hurt a bit from all the work but I was now a woman and loved how content I was as Trina. Belinda told me to fix my makeup as I cleaned some sticky cum from my cheek and touched up my foundation and cheeks. A fresh coat of lipstick and I was ready for more fun. My cock was still rock hard and I needed relief. Belinda told me to sit in a chair and jerk off into a cup. I was ready and in less than a minute, I spewed my own cum in the plastic cup. I must have been quite a sight, dressed as a beautiful girl and jacking off into a cup. She then told me to drink it and without hesitation. The warm fluid ran down the cup as I slurped it all up. I was now a true cum swallowing, cocksucking whore. Belinda had me sit on a chair as she put a blindfold on me and handcuffed my hands behind my back to the chair. My legs were tied to the chair too making it impossible for me to move. She told me she had more things planned as I sat there wondering what else could ever be done to me. There was a knock at the door as I heard Belinda chatting with a guy and a girl. She asked them in and the three of them laughed a bit as they touched me, blew in my ear, played with my tits and rubbed my sleek legs. Belinda told me to lean forward as I felt a warm hard cock in front of my face. The blindfold was removed and Belinda said, "Go ahead Trina, You're quite the cocksucker. I'm sure Kevin would love to experience your new found talent." I looked up and Kevin was a stud. His thick cock was perfect and my tongue and mouth went to work on his throbbing tool. Without me stroking him, Kevin grabbed my head and fucked my mouth like he would fuck a pussy. His cock went deep into my throat and I gagged a few times as I could feel him touch the back of my throat. He finally blew his wad in my fuck hole and boy did he cum. The first load was enormous and I had trouble swallowing it all with some dribbling down the side of my face. The next eruption was almost as big but I could handle it, the third was less and I knew he was almost spent. I was told not to swallow it all and held a big wad in my mouth. He pulled his cock out as I tried reaching forward to clean it. He laughed as he ordered his girlfriend Mimi, to clean me up. Mimi came up in front of me and began kissing me, tonguing my mouth as if she was reaming me out. He lips were soft and heavenly and her taste was incredible. Her tongue was almost as long as Kevin's dick and she sucked out any cum that remained inside me. She then licked my cheeks and neck, cleaning up the cum that escaped from my mouth. Once she was finished, she stood up and went up to Belinda locking lips with her. This turned me on like no tomorrow watching this girl sucking face with my shemale girlfriend and sharing the cum of her boyfriend. I could never have written anything so crazy or even thought something like this could ever happen to me. The two "girls" finished kissing and Kevin ordered his girlfriend to drop her skirt and panties. She dropped them both and stood there rubbing her shaved pussy. Belinda uncuffed me and untied my legs as the girl got sat on the couch with her legs spread. She guided me over to the Mimi and had me eat her out. I loved pussy and went too town on her, licking her wet lips, inserting my tongue deep into her and sucking on her hard clit. Mimi writhed in pleasure under me and ground her pussy against my mouth urging me on. I sucked on her wet pussy making sure I hit all of her buttons. She screamed a few times telling me not to stop. I could feel her shudder knowing she climaxed but she held my head in place making me suck some more. I felt someone playing with my ass and my dress was raised and hose and panties lowered again. Kevin laughed as he pulled out the wet tampon from my ass. He got behind me and his cock slid right in my waiting hole. This was everything I could ever imagine. Trina was eating out a wet pussy and being fucked by a stud. Belinda had prepped me for his even thicker tool but this time there was pain because he was so big. This didn't stop me as I pushed back to meet his thrusts. My moans were a mixture of pain and pleasure. He came inside me as I brought Mimi off again. Kevin pulled out and Belinda shoved another tampon up my ass so I could keep his seen in me. Mimi pulled my head away and laughed at how smudged my makeup was. Belinda helped me stand as I fixed my panties and hose. My ass hurt but also felt empty. Kevin grabbed me and laid his lips on mine, licking my face and sucking on my tongue. His lips were hard and rough and I could feel the stubble of his beard against my face. All of this was an extreme turn on as I responded to his kiss. He pulled away as I saw Mimi and Belinda making out. They broke off the kiss and Mimi grabbed a hold of Kevin's arm. Belinda kissed Kevin quick as they whispered to each other. Kevin and Mimi then left our suite and Belinda turned back to me with a smile. "Well Trina, so how was your night of firsts?" I stood there blushing like a bride on her wedding night. I had been fucked twice, sucked two cocks, ate out a beautiful pussy, and swapped cum with a shemale and a real girl. The only thing better would be a video of the entire event so I could jerk off as I watched it at home. Belinda told me to clean up so we could go to breakfast. It was 6 AM and we had been up all night. I fixed my makeup making me pretty again and Belinda threw me a slinky tight dress to put on. It had long sleeves with a draped neck that showed off my tits. It was a show stopper and it clung to me making me feel very pretty. Belinda dressed in a tight leather skirt and see through top. Her bra was visible and her tits looked fabulous underneath. She was truly a very beautiful girl. We walked arm and arm to the hotel restaurant. By now I felt very comfortable as Trina and also loved how my ass wiggled as I strutted down the hall showing off my cleavage to onlookers. Belinda loved how I got into being Trina and giggled as I flirted with one of the guys in the elevator. When he left she slapped my hand telling me I was a naughty girl. Was this ever fun. We sat and had breakfast. One of the guys in another booth kept eyeing me throughout our meal. I would look back at him and smiled. I just loved all the attention. They guys left and Belinda and I got up to leave. To my amazement, the guy I was flirting with came up to me and told me he just had to meet me. He thought I looked beautiful. My stomach flipped hearing that I looked beautiful. He said he was here for a weekend conference and had to get back to the meeting but he wanted to see me again. I stuttered a bit and then shook my head yes. I agreed to see him later that evening. I was Trina for two days and so what the heck, I may as well go out with a bank. Jeremy took my hand and kissed the back of it saying he would meet me in the lobby at 5PM. He told me to wear something sexy too. I would love what he had planned. Remembering Belinda, I asked him if she could join us and if one of his friends needed a date. Jeremy loved the idea and said he would arrange a double date for us. He kissed my hand again and off he went. Belinda came back from the "ladies room" and I told her all about my beaux. She was impressed that I worked so fast and was excited too. Belinda and I spent the day shopping as two sexy women. We got hit on almost every hour by some great looking guys and some real dogs. It was fun playing with them though and letting them down. By 3PM we had shopped ourselves out and had to get back to change into something sexy. Luckily, I found a very short dress, in hot pink, that showed off my curves as well as my beautiful tits. I couldn't wait to wear it and really turn Jeremy on. Belinda already had something in mind for herself. We were gushing with enthusiasm as we got to our room. After a quick shower to clean our bodies of sex, we dried off and fixed our makeup. Belinda helped me put on a sexy pink push up bra that made my tits look even better. The cincher helped with the curves to so I kept it on. I changed gaffs to make sure I was all tucked away. A beautiful pink pair of lacey panties came next and made my ass feel smooth and silky. I chose pantyhose for tonight's event. Garters and hose are pretty but can become a real pain. Belinda helped me into my new dress and it fit perfect. It clung to my hips, outlined my bulging tits and made my ass look great. Belinda had chosen a red strapless number that showed off her natural cleavage as well. We were to hot ladies ready for some fun. It was ten minutes to five and we fixed our makeup, sprayed on some perfume and grabbed our purses. The boys were waiting for us I the lobby. Jeremy looked like he saw a ghost as he followed me through the lobby and up to him. He smiled saying he had never seen anyone as beautiful. I blushed from embarrassment. If he only knew my little secret. We took a cab to dinner and Jeremy and Scott were perfect gentlemen. It was so nice having them hold our chairs as we sat, stood up when Belinda and I went to the little girls room, and even stood up when we returned. I got goose bumps just thinking about how wonderful I felt and how I was being treated. Belinda also got in the groove and was playing with her dates hands and arms, caressing them as she leaned next to him and chatted. Jeremy was still a gentleman and seemed to wait for me to make a move. After dinner, the guys suggested we go to a club nearby to dance. I had never danced as a girl before but again, this was a night of firsts. The club was alive with all sorts of older people. It felt natural being around people our age. We were seated in a booth and Jeremy ordered Champagne all around. I always got a tickle from drinking Champagne but loved it anyway. We clinked our glasses and sipped our drinks while Scott and Belinda seemed to get to know each other better. Belinda was now rubbing Scott's crotch while kissing him. Jeremy and I sat quietly as he slowly put his hand on top of mine. He made the first move as I responded by putting my hand on his leg. We looked in each others eyes and he leaned forward and softly kissed my waiting lips. His manly smell was intoxicating as he leaned back with a smile. I dipped my head and he lifted my chin coming in for another kiss., This time he meant business as our lips melded together and our arms reached around each other in a tight embrace. Our tongues played together and I sucked on his long tongue letting him I loved the attention. We made out for a few minutes and Jeremy broke away asking me if I wanted to dance. I nodded and he helped me out of the booth, putting his hand on my back and leading me to the dance floor. Of course it was a slow song and I had to remember how to hold him like a girl and not lead. He pulled me close to him and we swayed to the music, oblivious to anything else happening in the club. My head was on his wide chest when I opened my eyes. The songs changed and we were still dancing away. Something caught my eye and I tried maneuvering myself in position to see if what I saw was real. In the corner of the club were a lady and gentleman sitting next to each other and drinking cocktails. They were sharing some kisses and I could tell she was stroking him under the table. I didn't recognize the guy but the girl.......the girl was my Melissa. Melissa had lied to me about going to see her mother and was here with another man. I began to fume thinking she was cheating on me and everything was a lie. I wanted to go confront her but had second thoughts. I was Trina and looked like girl. What would Melissa think or say about me dressing like a girl. Even though I was pissed, I remained calm and tried not to react. The song ended and Jeremy led me back to the table. Belinda and Scott were getting on famously when they said they would meet us for breakfast tomorrow if that was OK. Jeremy and I didn't object and Belinda asked me to join her in the bathroom before she left. Once inside the women's sanctuary, we began fixing our makeup I the mirror. Belinda told me she informed her date that she was a shemale which excited him. She even told Scott that I was a crossdresser. Scott told Belinda that Jeremy was bi and that he wouldn't have any problem with me being a guy. This was really weird but I told myself to go with the flow. I told Belinda about seeing my wife and she just laughed. "See, everyone has a little bit to hide, now don't they?" she said. I grinned at her and the door opened to the ladies room. It was Melissa and I was here dressed to the nines. Melissa went to the mirror and fixed her lipstick, primped her hair and put on some perfume. She glanced at me in the mirror and smiled at me. Obviously she didn't recognize me and thought I was just another girl. I nervously took my lipstick and put on a fresh coat. I was shaking a bit and missed an edge. Melissa saw my mistake and reached over to fix it with her finger. She was face to face with me and said, "There now, everything's in order. I'm sure your dates will love how pretty you look tonight." I thanked her and told her she looked very beautiful too and that her date is a very lucky man. She laughed saying it was only for the weekend so she had to make the best of the moment. She then went on to say he was rich, fun and had a huge cock. She laughed again as she finished primping herself. I was totally crushed. Melissa opened up to a "girl" in the bathroom she had never met before but never said a word about how she felt to me. But then again, here I was, dressed like a sexy girl, sharing girly secrets with another woman. Melissa finished and kissed me on the cheek, wiping away any lipstick. "Take care hun, I'm sure you and your date will have fun too." She turned on her heal and was gone. Belinda had heard the entire exchange from the bathroom stall and came out. She asked me who I was talking to and I told her it was my wife. Belinda broke out into a huge fit of laughter. After composing herself she said, "Well Trina, it's obvious you handled yourself like a real girl. Your own wife didn't recognize you. Now that's one for the record books." She took my hand and I laughed too. I did pull it off. I was still mad but saw the humor in the situation. "Let's go, I have a hot date. I'll use our room if you don't mind. I'm sure Jeremy has plans for you too." We rejoined the guys and Jeremy took my hand in his as Scott and Belinda were arm in arm. We took cabs back to the hotel and Belinda and Scott said goodbye as they went directly to the room. Jeremy suggested a nightcap and we sat in the lunge as he told me about himself. I tried sitting as feminine as I could, crossing my legs and letting him see up my dress now and then. I could tell he was hot and his words seemed to mumble a bit. He then leaned forward and quietly said, "How about we take our drinks to my room? I'm sure it will be more comfortable there." I nodded and he took my hand, helping me out of the chair. He slipped his arm behind me and pulled me close to him as we made our way to his suite. Once inside he set our drinks down and came up to me, wrapping his arms around me and reaching forward as our lips met in a sensual kiss. His body was strong, firm and I could tell from the pressure on my leg, he was extremely hard. I responded to his kisses and pulled his head to mine as we enjoyed the moment. Coming up for breath, he told me I was very beautiful and that Scott told him my secret. Well, the cat was out of the bag now. He said he found me attractive the very first time he saw me in the restaurant and thought about me all day. Being a "girl" with some extra parts made him even more excited and he couldn't wait to get me alone. By now I was getting very hot and bothered and wanted this man. My hand reached down and found his massive member in his pants. I smiled at him and he told me he wanted me to strip for him. Jeremy sat on a chair as I tried my best to act as feminine as possible and strip for him. I danced a bit, wiggled my ass for him and pulled up my skirt exposing my panties. The zipper on my dress slid down easily and I let the shoulders fall off as it dropped to the floor. Here I was standing in front of him in only my bra, hose, panties and heels. His wide smile told me he liked what he saw. Not wanting to show too much too soon, I slowly dropped to my knees in front of him and helped him remove his pants and shoes. His cock sprang to attention in his boxers. Helping him remove the boxers, he sat there in all his glory with his 7 inch tool standing at attention for me. My head lowered to his throbbing member and I licked his entire shaft, paying close attention to his tip. The taste of his cum turned me on and I made sure I didn't miss a drop of any pre-cum. He sat back with his eyes closed as I took him into my waiting mouth, carefully making sure not to bite him. My hands were stroking the base of his cock while I bobbed up and down on him. I would then lick his shaft again and take him in trying to get him to cum. He let out a moan and then said in a rough voice, "I'm going to cum." I could tell he was ready. His shaft seemed to expand in my mouth as I felt a rush of his seed fill my mouth. Before I could swallow, another rush filled me. Quickly, I gulped down the load in my mouth before he could fill me again. This time it was less and I could handle it. Another spasm and Jeremy had shot his wad. I could taste the warm, salty cum throughout my mouth and licked his cock clean. Jeremy stroked my head as I laid my head on his lap next to his softening member. I was caressing his hairy leg and we just seemed to enjoy the moment. He then had me stand and reached around me, lifting me into his arms. This was something right out of the movies as he opened the door to the bedroom and laid me carefully on the bed. He finished undressing as I removed my hose, panties, gaff, and heels leaving my bra on for support. I slipped under the covers waiting for him to join me. Jeremy came back and climbed under the sheets next to me. The rest of the evening was so tender and sweet. Jeremy went down on me and took everything I could give. He played with my ass, fingering me while he blew me. He would then come up to me and we would make out, tasting each others seed in our mouths. Jeremy didn't get hard again but told me he would make me happy in the morning. We held each other and drifted off to sleep. The alarm woke us at 6AM. Jeremy had a class at 8AM so we had to get ready. Before we got up, he kissed me, rubbed my soft skin, played with my ass and whispered in my ear, "I really want you Trina." I knew what he wanted and got into position for him. My ass was ready for the taking. His cock was hard and he slipped into me without any effort. My ass was still very wet from last night's activities and his cock felt so filling inside of me. My body seemed to respond to his thrusts by backing into him. He reached around and grabbed my tits as he fucked me silly. He exploded in my hot ass and I could feel his cum fill me up. He pulled out as I rolled over in bed. He came up and laid next to me as our mouths met and our bodies seemed to meld together in a moment of passion. Jeremy broke the kiss and told me he had to get ready. I was feeling sad but knew this had to end sometime. Jeremy got up, showered, and shaved as I put on a gown and robe. I also inserted a tampon in my ass to keep from dripping Jeremy's cum all over. I felt so girly inserting the tampon and leaving the little string hanging from my ass. My face needed attention and my hair was a mess. We must have really had fun last night. Jeremy finished as I washed my face and brushed my teeth. Without makeup I thought I looked pretty rough, not feminine at all. Jeremy thought otherwise and pulled me in his arms, giving me a soulful kiss and stroking my face. I was delirious and never wanted the moment to end. It did though and Jeremy grabbed his coat, kissing me one last time before he left the room. I was now alone, dressed very sexy in a silky gown and lost in my feelings. I sat and just stared at the TV waiting for Belinda to return. Jeremy didn't even leave a telephone number or address so I could contact him. I even felt a few tears form in my eyes. What a girly way to act really. Belinda knocked and then came into the room alone. Her date had to go to the conference too. She began to tell me about her night and how wild sex was. I just listened and told her my night was OK too. She came up to me and held my hand, "What's the matter babe?" I burst into tears as I told her about how sexy and gentle Jeremy was and that he didn't even leave me his name, telephone number or address so I could contact him. Belinda just listened and then looked at me with a smile. "Maybe you didn't get any info dear but Jeremy and Scott are roomies and I got all the details of how to contact them." My tears turned to joy when she gave me all of Jeremy's personal information. I knew at that moment, my life would never be the same and that I was destined to search out my lover. xxxxxxxxxxxxxxxxxxxx Belinda and I parted company later that day and I told her I would contact her when I could get away again. I didn't see Jeremy again but did enjoy meeting up with other guys in similar situations during work trips or even when Melissa went "away" to her mothers. Belinda and I became very close girlfriends and she was always there to help me become the girl of my dreams. I knew living with Melissa was a sham but never divulged to her that I knew her secret and I'm sure she never knew mine. My adventures continued as Trina and there were more juicy times that followed. Until next time............ Trina