8 comments/ 45020 views/ 15 favorites You Got the Part! By: Checkmate215 Coming up with the rent every month was becoming more of a challenge. I was a on again off again actor/waiter. My tips were good but I had to supplement them with acting gigs and odd jobs. This was the price to pay for freedom. I had a one bedroom apartment that ran me 1500 a month. I was avoiding taking on a roommate at all cost. I loved my privacy. A friend told me a new theater group was forming and they were starting a production soon. It wasn't a paying gig but I never shied away from becoming a better actor. I sent the director an email with my résumé and expressed my interest to join up. He responded with the info to come and audition for their first production. I arrived at the theater at 6 pm. There were a few people standing and sitting around. I asked one of the guys for Greg the director he pointed me down front. In front of the stage was Greg talking to a young woman. I excused myself and introduced my self. "Excuse me Greg hi I am Aaron." "Good to meet you Aaron, did you receive the lines I emailed you? We can get right into it." "Sure lets do it I said excitingly." My character's name was Simon. I went through the lines with one of the cast members. I really thought I did a great job. Greg seemed to be deliberating with who I assumed to be his assistant director before he told me to have a seat and he'd be with me shortly. Shortly was an hour and a half later when everyone was either gone or in the lobby saying their goodbyes. "So, Aaron I really think your a good actor and I have something in mind for you." "Ok that is really good." "Well how do you feel about wearing women's clothing?" "Beg your pardon." "Yes, the part of Riley is a much bigger part than that of Simon. Riley is the crossdressing neighbor of our two main characters. He/she has a lot of lines." I thought about it. Dressing up didn't really bother me. A lot of successful actors have done it, it just caught me by surprise. Greg went on to explain that I didn't have a hard face and that I could really bring life to the part. Depending on how rehearsals went he could even do some re-writes to expand the part. I didn't know if I should be offended because he thought I looked a little feminine but I decided that I wasn't. "I will take the part." "That's great welcome to the cast" Greg said excited. He gave me a copy of the script and told me to see Jess our costume/makeup artist before I left. I went backstage and found Jess organizing costumes and other things. "Hi, Jess I am Aaron good to meet you." "Hi Aaron, likewise what can I do for you?" "Greg asked me to see you before I left." "What part ya got." "I have Riley." "Whoaaa! Good man" she said as she laughed." She measured me with the tape measure she had around her neck then asked me my shoe size. She handed me a wardrobe bag and a bag with two shoe boxes. "If you have never worn high heels before I suggest you practice everyday at home. Don't worry about the makeup I will handle that before you hit the stage. I also have your stage wigs here but I will give you a practice wig for home. Every thing else you need is in the bag. Glad to have you aboard." "Thanks." That was all I could muster at this very moment. I was still processing what I was about to get myself into. I said goodbyes to everyone and headed home. I stopped and picked up dinner some tacos from the Taco Bell value menu and went home. Once I got in I flipped on the Tv and began eating. Was it to late for me to bail out? That certainly wouldn't make me a better actor. I decided to man up and embrace the part of Riley the crossdresser. I opened the bag she gave me and in it was two dresses a black one and a red one. On the hanger with the red dress was a wide patent belt and a similar styles black leather one with the black dress. There were a few pair of pantyhose along with a smaller bag. Inside the smaller bag was a all in one body briefer padded in the hip and butt area along with bra and panties and to gel like breast that could be attached with the adhesive included. This was going to be a chore. I was clearly out of my element I had been a straight guy all my life. The next day at a script read I pulled Jess to the side. "Jess, you have a minute?" "Sure, Aaron what's up?" "We'll I am having issues with the wardrobe and could really use some help. It's something I had never done before." "I understand, I'll tell you what. How about I come to your place and we can put everything together. I will even bring my makeup so you can see what you will look like on stage." "Sure that would be great." After we finished up Jess and I headed back to my place. She told me to undress I took my clothes off. I was standing there in my boxers. "C'mon chief lose the man panties." I laughed hard though I was so nervous. Jess was an attractive white girl 5'5" curvy with long brown hair and eyes. I took off my boxers and displayed my 8" semi erect cock. I considered myself average especially for a black guy. "Ok, someones happy to see me." Jess joked. She made me laugh which made me less nervous. "We are going to start with that guy." Jess pulled out what look like a roll of wide medical tape. She took my now fully erect cock and tucked and taped it back and out of site. It felt so strange. She popped the tags off and handed me the panties. I put them on they felt so smooth. "Next time we will be shaving those legs Mr." She then help me into the sheer black pantyhose and the padded body briefer which gave me a shape. Before she pulled the straps to the briefer up on my shoulders she attached the breast using the adhesive put the bra on me and pulled the briefer straps up. She slid the dress over my head and pulled it down it was much more form fitting than I thought. She zipped me up and told me to have a seat. Sitting down was a chore I couldn't even open my legs because of the tightness of the dress. The finishing touches were the wig and the makeup. She was truly an artist as she applied all types of foundations eye makeup lashes and lip gloss. When she handed me the mirror I didn't recognize myself. I looked good to be a man in drag. I certainly was what they referred to as passable. Last but not least she handed me a pair of 5 inch heels out of the box. They were black leather. I slipped them on each foot an true to stand this was going to be a challenge. She spent the next 3 hours showing me mannerisms how to sit and walk. I was still shaky but I was improving. "By first dress rehearsal you will be running in those heels, with reactive of course." "Now I see why women come home and rush to get out of them." Jess laughed ,"But they make you and all us women look sexy though." Looking in the full length mirror I had to agree. Jess helped me get out of my costume. After stepping out of the body briefer Jess push me back against the wall. She pulled down the pantyhose and panties enough to untape my now sore from being hard so long penis. She massaged it until the soreness was an afterthought. She sank down to her knees and took my erection slowly into her warm mouth. It felt so good I was so turned on. My back was on the wall opposite the full length mirror. I was admiring myself still in full makeup, wig, bra, breast forms, panties, pantyhose and heels. I looked hot enough that I would fuck me. She was now deep throating me as I moaned and continued to admire my new character in the mirror. She pulled her mouth as I clumsily exploded onto her face. I had to stabilize myself from falling over in my heels. That whole week I was Riley at home whenever I could. At the time of the dress walk through I was so ready. I got to the theater early to do hair and makeup. I got dressed and was ready for the stage. I saw the director Greg back stage before we started. ""Who's this have we met miss?" he laughed. "It's Ms/mr. Riley ready to hit the stage." "You definitely are Ms.." he said but this time not laughing as he looked me up and down. I chalked it up as assessing my wardrobe as a director and hoping he wasn't sizing me up. I was wrong of course. As he walked away he patted me on the backside and said break a leg. However his pat ended with more of a squeeze of my backside in this short tight dress that fell mid thigh. I looked around but everyone was busy off in their own worlds. The rehearsal went well i undressed and went home to relax. There was a knock at the door I was hoping it was Jess it wasn't. It was director Greg. "What's up, Greg." "I wanted to go over a few script changes of that's ok I want to give Riley a more prominent role." I was happy but uncomfortable at the same time. He asked me to go and change into Riley so he could be the full effect. I knew I was headed down a bad road. It took me about 35 minutes to transform into Riley. I went and sat down on the couch next to him and crossed my legs. We began going through the new lines as I could watch his eyes drift up and down my pantyhosed legs and thighs. I knew this was a recipe for disaster. He came at me in the middle of me reading a line. In seconds I was pinned under him with his tongues parting my glossed lips and invading my mouth. Why wasn't I stopping him? I wasn't gay. I had never desired a man. Riley made me feel so sexy and attractive. We switched positions. I now straddled him with my dress hiked up. His strong hands squeezed my ass and hips. I unbuttoned his jeans and pulled out his rock hard 7 inches. I kept telling myself I am not gay I am Riley. I took it into my virgin mouth. Slowly taking on enough not to trigger a gag reflex. He moaned while slightly tugging my wig. After 15 minutes and finding a rhythm he exploded into my mouth. He did whatever he wanted to Riley for the rest of the evening. I followed every command. I never knew I had a submissive side before but I loved taking orders from him. I loved hearing my stilettos on the hardwood floor scurrying to get him things from the kitchen and serving him. You Got the Part! Ch. 02 I was addicted to being Riley. Being Riley made me feel sexier than I'd ever had before. There are erections, and there are erections. I love the erection I get when, I give my pantyhose that final pull over my hips. Riley had given me a sense of freedom and enlightenment. I loved dressing in women's clothes. It made me feel so desirable. I was now spending most of my time as Riley. I was working at a bar downtown called the Electric Lounge. A friend had gotten me a job waitressing there. The tips were so much better than my old job. The increase in income helped me amass a very nice wardrobe. The sexier Riley looked the bigger the tips were. Electric Lounge was a hangout for Queens of all persuasions. I had gotten the job after auditioning for the owner. The owner Gigi wanted fresh faces for her new lounge. Gigi had become sort of a mentor to the "girls" who worked for her. It was a great job and plenty fun. There was always the occasional drunk, who wanted to play grab ass. We let security handle them. I was sitting at a table in the back room counting my tips. The night was over and I was beat. "Hey Riley, How'd you do tonight girl?" "Good Gigi, that bachelorette party table treated me well. I also had some out of town business men, you know the usual." "That's good, I know your going shoe shopping." "Or maybe a new wig, the price of custom wigs is going up," I laughed. "We'll go see my guy, he'll hook you up." "We'll see." "Good night, girl get home safe Riley." "You to, boo," I said as I blew air kisses to Gigi." It was around 5 am, I exited the bar and hailed a cab. It still amazed me how easy it was to get a cab in a little black dress and five inch heels. I had moved to a new apartment in the village because I needed more space. I got out of the cab at the corner of my street. There was a 24 hour diner that I frequented. I got a booth by the window and opened the menu. I was famished, hustling drinks all night in heels is a marathon in itself. My usual waitress Adriana came over. "Good morning, Miss Riley, how are you?" "I am good Ade how are you?, How's school?" "I am good and school is coming along, study study study." "Well, whenever you need a break come to the lounge. I will take good care of you. The performers are great and even involve the audience in their routines. You'd have a blast." "Do straight people come in?" "Yes, girl it's a place for everyone to come and have fun. A lot of our customers come just for a different experience." "I will put it on my to do list." "That's good, can I get a cup of coffee and the French toast combo." "Sure, how would you like your eggs?" "Scrambled please and bacon extra crispy." "Will do, be right back with your coffee." "Thank you, Hun." She was a sweet girl working her way through college. Her parents owned the diner and helped her as best they could. I pulled out my compact and started to touch up my makeup. I didn't know why, after I ate I was going home and to bed. It was force of habit. A young lady sitting at the counter gave me a look. I wasn't sure who she was but she looked familiar. She walked over. "Excuse me, I don't know if you remember but, you waited on my friends table tonight. The bachelorette party," she said. "Oh yes, you guys had a great time, right?" "We most certainly did, do you mind if I join you?" "Not at all please do." She went and got her jacket and hand bag and sat across from me. "I'm Taylor," she said as she extended her hand." "Well for right now I am Riley. Later on I maybe someone else," I laughed. She laughed as well as we both took a sip of coffee. "Riley, you look amazing and before you told us we didn't know you were a man. We knew the Electric lounge had drag performers but you guys look amazing." "Thank you so much, girls love compliments," I said and batted my eye lashes. We both laughed some more. Taylor was a very attractive young woman. She was 5'6" maybe 140 pounds. She had beautiful ebony brown skin and very nice facial features. Her body was curvy but well toned, like she frequented the gym. Her long black hair was silky and had great sheen. Though I fully embraced Riley, I could still appreciate a beautiful woman. Our meals came and we talked the whole time as we ate. I learned that she was an estate attorney and lived in the neighborhood. She grew up in Jersey and always wanted to live in the city. I told her my story and she seemed to hang onto every word. "Riley, do you mind if I ask you a personal question?" "Not at all," by this time I felt comfortable enough to answer anything." "Have you ever been with a woman?" "I have, I am attracted to women and men. I guess you can say I am bi-sexual, though most men who cross dress are straight." I could see curiosity as well as intrigue in her eyes. There was definitely an attraction there. We finished our coffee, Taylor insisted on picking up the check. We exchanged numbers and said our goodbyes. I couldn't wait to get into my bed. After kicking off my 5 inch heels I removed my wig and makeup. The shower was so refreshing after a long evening. I was off the next day so I could rest all day Sunday. Wiping the condensation from the bathroom mirror, there was Aaron. I didn't see much of that guy nowadays. I laid down and closed my eyes. My text message alert went off a minute later. It was Taylor. "Hi, Riley hope I didn't wake you." "No you didn't," I lied. She was an attractive woman. Aaron wanted to fuck her and Riley wanted to be her. "What are you doing?" I lied again. "I am getting ready to get undressed and get into bed." "You're still dressed? You looked so good tonight in that little black dress. Your curves were so amazing and your legs were so great." "Yes getting undressed in a minute. Thank you sweetie, your making a girl blush over here. As far as my curves go I owe them to some great padding. Now the legs they are all me." I said I was still dressed to set the bait, and she took it. "Wish I was there to feel those sexy legs and curves in those silky pantyhose." "Wish you were to." I waited to see if she would take the bait and she did." "Text me your address I can be there in twenty." This was my opportunity to go in either direction. What the hell? I texted her the address and jumped out of bed and did a mad dash. I fixed up my makeup and wig. Squeezed back into my padded body shaper and pantyhose. Lastly put on my dress and shoes before the bell rang. Taylor wasted no time once I opened the door. She kissed me immediately parting my glossy lips with her tongue. My gloss and her lipstick melded together tastefully. She pushed me down onto the ottoman and straddled me. She continued the kiss as she began to pull my dress up. She reached inside my panties and hose and pulled out my stiffened cock. She stroked it roughly, she definitely wasn't here to make love. I loved her aggressiveness, it made me feel so feminine. She removed her heels, hose and panties. She pulled a condom from her clutch and began to roll it down my hard member. Taylor mounted me like a prized stallion. She wasted no time inserting me into her moist slit. Her face was overtaken by pleasure. Laying on my back across the large ottoman, I was being taken. This was the first time Riley would be taken by a woman. I was quite sure it wouldn't be the last. She moved up and down with slow but powerful movements. Her thick hips powered her up and slammed down on to me again and again. My five inch heels planted firmly to help me sustain the onslaught. "I wanted to fuck you since I first laid eyes on you," she said as sat up and pulled her dress over her head. I reached for her firm supple breast and she slapped my hand away. "I'm in charge here, bitch!" I was taken aback by her words, but also excited. Riley loved to be dominated and I played into Taylor's lead. My moans became louder and more high pitched. I got off on not having any control. "I watched you prance your prissy ass around all night. I felt like you were teasing me with that sweet ass of yours. You fucking pretty bitch." Though I'd had sex, I hadn't been completely dominated since Greg. I loved to be dominated, ran through my mind. Her forceful thrust had slid my body up the ottoman. My heels now flailed helplessly off the floor as she had her way with me. Each time she came down her vaginal muscles wrenched my erection with pleasure. I finally succumbed and exploded into her, filling the condom. As the semen squirted out I felt emotionally drained. Taylor unmounted me, got dressed and left without a word. I was stunned but was left wanting more. I felt so used yet it felt so good. I laid there looking up at the ceiling. My dress pulled up with the full condom on my softened cock. I undressed showered again and went to bed. I got up around 4 that afternoon, made tea and a bagel. I checked my phone and I had 1 new text from Taylor. "I will see you soon." That message was so cryptic to me. I felt like I was left with a cliffhanger, at the end of a good book. Clearly things were going to be on her terms, and I didn't mind. I was excited at the thought of letting go, and having no control. The rest of the day I went through my usual Sunday rituals. I cleaned, did laundry and got prepared for the week ahead. Every 10-15 minutes I would check my phone, no text from Taylor. By Monday I still hadn't heard anything yet. The waiting was mind numbing, I couldn't think of anything else. I got to work around 7:30pm, and still nothing. I changed into a tight red sequined dress and started my makeup. All the girls always amped up their makeup for bar crowd. Gigi felt it made the customers enjoy the experience more. "Hey, Miss Riley, How was your day off?" "Miss Gigi, my day off was great, sort of." "Sort of?" "Yes, I met someone and had a great time when I left here Saturday night. She hasn't called me yet. Her last message said "See you soon?" "That's rather vague, and you said she?" "Yes I did. She was here that night with the bachelorette group. We had breakfast and a little more," I laughed. "Well what ever floats your boat. Remember, I told you about these customers. Don't let them use you for there little erotic fantasies. They think because we do what we do, that we're all sex fiends. Well I am a respectable lady, born with a penis," she laughed. Gigi was right many customers were looking for, what they couldn't get at home. It didn't deter my interest in Taylor. I had a burning desire in me to be controlled. It fueled my innermost passions. I had drifted off in the middle of Gigi's warning speech. In that moment I was being driven into my ottoman looking up into Taylor's eyes. I finished up and headed out to the floor to start my shift. Still no text. Monday nights mostly regulars came into the bar. I kept their drinks coming and chatted them up. I took my break around eleven, I went to the back to check my phone. One new text, from Taylor. I smiled inside and out. Her text said, "You look great in red." A jolt went through me like electrical current. She was here? My tucked erection wanted free of its panties and pantyhosed walls. I could feel myself losing it, just a matter of time. Pre-cum was on its way, I gathered myself boy and thoughts. I fixed my hair and makeup, straightened my dress and walked back to the bar. I scanned the entire place and their she was. Taylor was at a corner booth alone in another waitress's section. I hadn't seen her there. The girls here get a little snippy if you try to poach one of their customers. I sexily walked over and sat next to her. I purposely didn't pull my dress back down as it had ridden up a little. She wasn't subtle about checking me out from head to toe. Red sequin five inch heels to match my dress, skin toned ultra sheer pantyhose and hair and makeup impeccable. She crossed her thick thighs towards me. Taylor had on all black everything. Suede platforms stilettos, black pantyhose with a seam, skin tight black bandage dress. My hard on had now turned into a sore throbbing problem. My taking her in was interrupted by my coworker Alexis. "Riley are we going to have a problem? Are you trying to steal my beautiful customer away from me?" Before I could get anything out, Taylor jumped in. "No honey, Riley is an old friend and I am yours for the night. I will have another Cosmo and Riley will have the same." Alexis raised an eyebrow, turn on her heel with a snooty look and walked away. I felt a rush from being protected, and a trickle of pre-cum. "How are you Riley?, you look beautiful this evening." "I am very well, thank you for asking. You looking very stunning." "Thank you." "What time do you get off tonight?" "3am." "I am going to text you my address." "Ok, I will be there." Alexis had returned with our drinks. I had to get back to work my break was ending soon. I took a sip, hoping it would settle me some. "I have to get back to work." "So soon," she said as she rubbed my knee. "Yes I'm afraid so," I said with a sigh, wishing she could rub me all night. "Well I am going to watch you a little while longer, finish my drink and see you later." "That sounds like a plan, don't watch me too hard," I joked. "I could watch sexy Miss Riley all night long." She leaned in for a kiss and I didn't move a muscle. The kiss was soft and sensual. The grip of my thigh with her French manicured nails was not. It was forceful and direct, she wanted me. It took every fiber of my being to stand up and compose myself. I was at a lost for words, I just walked away. She intimidated me and she knew it. I took a drink order from one of my tables and went to the bar to fill it. Gigi was behind the bar. "Miss Riley I have never seen you this flustered before." "Flustered?, what makes you say that?" "I say that because I have two eyes. I also say that because, you are afraid to look in the direction of your attractive lady friend over there. "My attractive lady friend?" "Yes Riley, the one that just kissed you and felt you up under the table." "You saw that?" "Stevie Wonder could have saw that. She definitely looks like the flustering type to me." That made me laugh and for the first time I looked across the room at her. She was watching me intently. I felt like the field mouse under the hawks gaze on the Discovery channel. Somehow I felt as though squeezing my legs tighter would stop my leaking pre-cum situation. I was wrong. I took my drink order to my awaiting customers. When I turned around she was gone. 3:00am could not come fast enough. I finished my shift and said my good nights. I hailed a cab and read off the address in the text. I was saddened every time we encountered a red light. We arrived and I scurried out of the cab and to the front door. I rang the bell for apartment 3F. "Come on up, Riley. You have to take the stairs the elevator is out of order." She could see me through the camera. I hope I look good. I started up the stairs, three flights. These were the most continuous stairs I'd taken since becoming Riley. I was exhausted when I finally reached the top. Taylor was at her door waiting for me. She pulled me in and press me to the now closed door. She took what little breath I had away with a deep kiss. Her moist mouth taking what she wanted from mine. She released me and I took a step forward. Her apartment was well decorated but not tidy. There were pillow and clothes thrown about all over. It wasn't dirty just a little messy. She was wearing what she had on at the club. She came around behind me and put her arms around my waist. She swept my hair away from my neck and began to kiss me gently. She took me by the hand and led me to the bedroom. Hawk, field mouse popped into my mind. She unzipped my dress and pulled it off my shoulders. This was unlike our first time, this was slower and more deliberate. She dotted me with kisses from one shoulder across to the other. It was so exhilarating. Pulling my dress down I stepped out of it. I removed my body shaper, pantyhose and panties. I felt exposed sitting on the bed before her. I had put my stilettos back on and still had my breast form filled bra on. She turned and went to her top drawer and pulled out her strap on. She started to undress. She peeled herself out of her tight dress. Her body was thick and taut. She put the strap on over her seamed pantyhose and panties. This wasn't my first cock but it was my first fake one. It was 8 inches and had girth. I took it in my mouth slowly inch by inch. She put her hand on the back of my head and moved me back and forth. I ran my fingers up and down the seams of her pantyhose on the back of her legs. She had no objections to me touching her this time. I continued sucking and stroking her legs and round ass. Her hands were now cupping each side of my face. She pushed me back onto the bed. After lubing the strap on and applying some to my entrance she was ready. She pushed through the initial resistance and inserted the head. I moaned in euphoric delight. I could see her responding to my sounds as she moved in further. The further she moved in the more I growled. She was now the full 8 inches deep inside me. I felt the fullness of it, and liked it. She began to kiss me again swirling her tongue with mine. As she started to move in and out of me, I purred like a stroked kitten. I could feel the front of her pantyhose rub my ass cheeks with each motion into me. "Riley, your a sexy bitch." I knew this, but loved to hear it aloud. She pinned my wrist to the bed above my head and increased her force and speed. I was now screaming. "Fuck me, oh fuck me." Taylor was doing just that. She flipped me over and entered me from behind. She must have had better leverage because her force increased in her thrusts. I screamed into the pillow, now stained with my foundation. Taylor was giving me all she had and I loved it. I felt her body jerk as she cum. She removed her soaked crotch pantyhose and unrolled a condom onto my stiff erection. I slid into her easily and felt her juices all over me. She rode me until I exploded into the condom. She continued to flex her vaginal muscles on my now flaccid member. I stayed until she left for work in the morning. The three block walk from her apartment to mine looked like the walk of shame. I fixed my hair and makeup before I left, it didn't matter. I didn't feel shameful I loved every minute of it. I was now the girl in the too tight too short dress coming home the next morning. It didn't feel bad. I undressed and showered. I cleared the condensation from the mirror, there was Aaron. I thought to myself "Riley has such a better life." I was famished I decided to order breakfast from the diner. The food came about 30 minutes later. I was surprised when I answered the door. "Good Morning, Adriana." "Good Morning, Aaron, Haven't seen you in a while," we both laughed. "Yeah, that bitch Riley keeps me hidden away." "Don't talk about my girl Riley like that," we both laughed again. "Since when do you do deliveries?" "I don't, I saw your order come in and needed some fresh air." "I feel ya." I paid her and sat the food on the counter. "Can I ask you a question?" "Shoot, Ade," I said as I opened the food platter. "Has anyone ever saw you, transform into Riley?" "Well in the beginning I needed help learning makeup and clothes so there was someone. She's a professional makeup artist she was very instrumental in creating Riley." "What about lovers?" "Never, that is such a vulnerable time for me. It would be like someone seeing both sides of me. I probably would be embarrassed." "You shouldn't be you are beautiful as Aaron or Riley." You Got the Part! Ch. 02 "You're so sweet." She walked over and have me a hug it was a long hug. She looked at me with those green eyes and olive skin and kissed me. We kissed for a minute before I realized, I had nothing going on down stairs. Riley would have been fully erect from a kiss like this. What was happening to me? I broke the kiss off and told Adriana I had to get going. She looked surprised, I was embarrassed and confused. She just turned and left with a confused look. Riley, Riley, Riley. As much as I loved Riley I didn't want to sexually castrate Aaron. I needed to know. I ran into the bedroom opened the drawer and pulled on a pair of panties. Instant erection. The phone pulled me out of my foggy state of mind. I answered it. "Good Morning, Miss Riley." "Good Morning, Gigi." "You sound very gloomy Gus this morning." "Yes, I just found out that my equipment only works for Riley." "That's not a big deal, you have desensitized your male self. I have to ask though, wouldn't you rather be Riley all the time?" "Honestly yes I would, but I thought it would be a voluntary decision." "Listen, your body knows and your heart knows your mind needs to catch up." ""I guess so, did this happen to you?" "Listen honey, When I knew I wanted to be Gigi, George didn't stand a chance. Aaron doesn't stand a chance either. Miss Riley has taken the wheel." Why didn't I see this coming or did I? "Anyways, I called you for a reason. How would you like to be my sidekick?" "I thought I already was," I laughed." "I'm serious, I mean on stage girl. I am going to tape my own show at the bar. Once I have a pilot my exec friend at LOGO said he'd give it a watch. We will see what happens from there." "Yes, because I need to work on my spin off already," we both laughed. "So you're in?" "I am, my acting gigs are slow right now. This sounds like fun." "Ok girl, when you come in tonight we will talk about it some more." "Ok, later Gigi." "Later, boo." That was great news I thought. My acting career had taken a back seat to real life for a while. I had to decide what to wear to work tonight. I received a text from Taylor. "I want to meet Riley for lunchtime two." "Ok send me the address." I was excited, maybe she wanted to spend time with me. Since I met Taylor it was all about sex, great sex. Was Riley a playboy or maybe girlfriend material? I needed to ask my self some tough questions. I was exactly sure I wanted the real answers. I met Taylor at her office around two. I decided on a not tight but form fitting gray dress, black pantyhose and 4 inch heels. Her secretary MIT have been out to lunch, I knocked on her door. "Come on in." Her bathroom had an adjoining bathroom I heard the water running. "Taylor." "Yes, c'mon in." She was standing at the sink washing her hands. Taylor was wearing navy slacks , a white blouse and navy blazer. Her navy heels could barely be seen under the length of her slacks "Hi Riley how are you?" "I am good." She dried her hands came over and kissed me. I ha a fire brewing beneath my dress. If this was my only vice Aaron would be out of luck. It was all about Riley. Once again I was pinned to the inside of a closed door. Taylor put her finger to her lips to let me know I couldn't make any noise. I didn't think that was a good sign. My dress hem was up around my waist instantaneously. Her brown eyes bore holes through my soul as she untucked my stiffened friend. She began to stroke it as she looked at me, try to contain myself. It amused her. She continued to stroke as she move to my side. She pulled my panties and pantyhose down to my hips with her free hand. She began to tease my entrance with her finger slowly inserting it in. I had to firmly put my back to the door to maintain balance in my heels. She was now stroking one end and finger fucking the other in unison strokes. My left hand was now holding a wall for added support. My right hand had to cover my mouth because I didn't trust myself. During this, for a brief second I felt bad for Adrianna. Riley was a selfish bitch, but I loved her. I stood in front of the sink in Taylor's office cleaning myself up. I had shot my load all over the tile floor. How long would Riley be so carefree? I wanted more. I straightened my dress fixed my makeup and walked into Taylor's office. "What is this?" "What is what?" "This between us?" "We are having fun, I enjoy it and I know you do to." "I do but I want more. I want to get to know you., not just be your kinky fantasy." "Let's do dinner tomorrow night, your place." "That sounds good." "We will eat and talk, then I will make you scream," she laughed. "We'll see about that," I knew she'd make me scream. I left her to get back to work. I headed home to change and relax before I headed to the bar. I got to the bar at my usual time and went into Gigi's office. "Hello, Queen bee." "Hi, Boo." "So what's the good word?" I took a seat in front of Gigi's desk. "Well honey, I have some paperwork for you to peruse before signing. I want to start shooting in two weeks. It is going to be a partially scripted show about, yours truly. My life, shenanigans, and hi-jinx. There will be a storyline and a loose script. Everything else will be off the cuff." "Sounds like fun to me." "It will be if we get picked up." "I know that's right. I will look these over and get them back to you." I didn't want to tell Gigi about my lunch meeting with Taylor. "Ok let me get my shift started see you in a few." The next day I was so anxious. I was drawing a blank standing in front of my closet. Taylor was coming over when she got off of work. Dinner was nearing completion and I had to put myself together. I decided on a little pink and black tight knit dress. The shoes were a black platform 5 inch stiletto with pink spikes on the back. I was ready. Taylor arrived around 6:15, she greeted me with a huge passionate kiss and ass grab. We ate dinner and sat on the sofa with a glass of wine. "Dinner was amazing your a good cook." "Yes I can cook in other rooms besides the bedroom." "I see." "I wanted to ask you a favor. Would you look over some documents for me." "Sure." I handed Taylor the contract Gigi had given me the night before. She read through each page before handing it back to me. "This seems pretty straight forward. You won't be paid for filming the pilot, if its picked up then you will be paid for the season. Congrats I may be seeing you on the small screen soon." "Thank you, I'm so excited." "It will be good to know I had Riley the star in my bed," we both laughed. "You can have Riley the star in your bed after she's famous." "That's good to know." She reached over and stroked my knee. I wasn't going out so I purposely didn't wear pantyhose for easier access. We began kissing as her hand slowly started to push my dress higher up my thigh. I was tingling down below as she navigated me onto my back. My dress now pulled up she massaged my full erection. Taylor stood and removed her dress, pantyhose, panties, and heels. Her panties had an obvious dampness to them. She mounted me with a expert gracefulness, like a thoroughbred jockey. Her wet tight cunt felt like a warm glove. "I hope Riley is ready for an all night session." I was. I was also ready to rock this pilot and become a T.V. star. You Got the Part! Ch. 03 I would like to thank Mr_Owlow for all his assistance with editing this story. In typical Riley fashion I was in a bit of a situation. GiGi's T.V. show was a complete success and we were picked up for a second season. America was in love with the cast especially GiGi and myself. We were making the rounds on talk shows and late night. We were doing endorsements, cameos on other shows and walking red carpets. DI was having a blast, and making a ton of money in the process. I was loving life, it was exciting and fun. Riley was partying hard and enjoying life to the fullest. I had long since abandoned Aaron, he was an afterthought. The more time I spent as Riley the more I blocked out my former life, I was Riley full time. I hadn't given much thought to it all, everything was moving so fast like a whirlwind. Celebrity had definitely gone to my pretty head. The lights and the lifestyle were intoxicating. My present predicament was a byproduct of my new lifestyle. I stand here now with my form fitting black designer dress pushed up around my waist. My panties and pantyhose are down and bunched around my thighs. My executive producer's bombshell of a wife is on her knees reluctantly sucking my cock. I was pretty sure he ordered her from some Eastern European bride service. The not so natural blonde didn't want to do this, I could tell. Her face said it all, she was sucking the cock of a black transsexual at her husband's behest. She had to be coaxed by Steve and reminded that her generous shopping allowance hung in the balance. So here she was sucking me as he looked eagerly on. The buxom beauty was wearing the exact same outfit I was. That had to be one of Steve's details of his little fantasy. As she noticed Steve's reaction she got more into it. His moans increased the more she sucked. The moans were spiced with intervals of, "Oh yeah baby." I guess she figured a better performance would win her husband's favor and his checkbook. Steve was an entertainment executive, he was all about the show. She began going deeper and sucking harder. A slight moan escaped my glossy lips as I shivered in my black sequined five inch platform stilettos. I was giving Steve what he wanted to get what I wanted. Riley needed her own show and Steve could make a spin-off happen for me. He had the right connections within the network and his money talked. Steve had moved behind me I could hear his labored breaths. He was taking it all in and loved every second of it. He unzipped my dress and unhooked my strapless bra. My brand new D-cup breasts courtesy of the season finale tumbled out. Riley was also all about the show. Getting a boob job on national television didn't phase me one bit. I loved attention and this brought more my way. I was never going back to my former life so it was a progression of sorts. He slapped my ample ass obtained in episode seven, causing me to lurch forward. I told the surgeon to give me the Jennifer Lopez, and he did just that. My surgical team was the best in the business. All the publicity certainly helped my doctor's practice. Natalia choked a little as my cock hit the back of her throat. "Fuck her, and fuck her good!" Steve ordered in a throaty drawl. Tonight all of Steve's orders would be followed to the letter. I pulled out of her warm moist mouth slowly. I could see the pangs of uneasiness and humiliation in her big hazel eyes. A combination of saliva and precum hung between her mouth and my erection, it looked like a glistening rope. I guided her off her pantyhosed knees, navigating her body wrapped in her close-fitting carbon copy dress. She seemed more unsteady in her five inch heels than I did in mine. Her nervousness seemed to be fading a bit as we progressed. Steve motioned Natalia to turn around. He was directing us as if he had played this all out in his head before. I was glad I wouldn't have to look into those sad eyes as I took her. I felt a twinge of guilt as she bent over as Steve motioned again. She was a casualty of Riley's war with the fame monster, the fame monster was definitely winning that war. I slid the condom on and moved towards Natalia's taut round ass. She exhaled a long breath as I pulled her dress up. Steve was taking it all in and loving every moment of the sequence. I pulled her panties and sheer to waist pantyhose down in one motion. Though she was definitely participating against her will, her pussy was amply wet. I slid in with very little resistance. Though I preferred my womanly appearance, a tight pussy still felt good to me. I don't think she thought marrying for money would entail this. Here she was bent over her husband's desk being fucked by a black tranny. "Fuck her hard!" Steve yelled. Before we started we were instructed that we could not talk at all, I followed the instructions. I rocked back on my stilettos and rammed with all my force. A guttural moan escaped Natalia as Steve beamed with excitement. As I continued Steve lifted her face to witness the mixed emotions of pleasure and humiliation. I moved in and out of her at a steady pace. After a few minutes the noise of her wetness was clearly audible. Her moans became increased in volume and length. She was clearly looking to impress Steve and give him what he wanted. Fifteen minutes later her entire body convulsed as she climaxed. Her vaginal walls had clamped on to me squeezing out all of her juices. Steve pulled me by my waist out of her. He moved her aside and pushed me into the spot Natalia just vacated. It was my turn to get fucked. I was expecting so much and got so little. His hands were all over me feeling my ass and hips. Being felt up turned me on, I was starting to get into it. I took my mind to another place where my body was not. Steve wasn't exactly a beast but he wasn't attractive either. He was an average man with an above average bank account and power. After struggling to get his semi erect four inches inside me he started his awkward pumps. He was herky jerky with no rhythm at all. Even with clinching my anal walls he did nothing for me. I took pride in keeping my ass tight with the proper exercise regimen. You would have thought he was rocking my world, he was not. Steve was slapping my ass cheeks like he was fully in command. I think he got off on knowing he paid for my ass and it was his for the taking. Natalia was looking down at me with a look. It was a look that said, we were in a sisterhood of bad sex. Steve was truly terrible, he was done in a minute. He collapsed on top of me like he'd done some great feat. I was disappointed but the reward would be worth it. I felt pity for Natalia if this was his usual performance. The next day I met GiGi for breakfast at her townhouse. We sat in the breakfast nook as her muscle bound man servants waited on us. "So hoe was your evening? Oops I meant to say how," GiGi laughed. "Sure you did you evil bitch. It was good, I think Steve and I reached an agreement." "That's good, the World is yours girl, take what you can." GiGi's words were truly encouraging. "I am trying but I would have to say our fearless leader was quite disappointing," I said with raised eyebrows. "Oh my, lets leave that one alone, next topic. I have heard some grumbling from your other cast mates that you're a camera hog," GiGi exclaimed. "Fuck those bitches, they are a jealous brood. The camera loves me and the fans adore me. They have had the same opportunities that I've had. It not my fault they didn't seize the moment," I scoffed. "I am just letting you know, next season may have a few more cat fights," GiGi said. "Bring it on bitches." The other girls were pissed that I had stolen the spotlight. They hadn't confronted me, but they weren't stingy with the cold shoulder. GiGi and I talked for a while and finished breakfast. I did a little shopping before heading home to my apartment. I got a phone call from my agent asking me to meet him at the office. Upon arriving to the office my agent informed me that I was getting my own show. I was thrilled I called Steve to thank him but Natalia answered the phone. "Hello." "Hello, Natalia this is Riley, how are you? May I speak to Steve?" "He is in a meeting but he would like you to stop by his office right away," she said. "I will be right over," I said excitedly. "Ok see you soon," Natalia said then hung up. On the way over I just knew he would want a repeat performance of last night. I finished touching up my make-up as we arrived, the driver opened the door for me. Steve's office was in an office tower with huge glass windows. I thought to myself "Riley, you're a bad bitch," as I checked out my reflection. I had come so far so fast, one role had changed my life forever. That little stage play had led me to a different life. I felt the men's eyes on me as I sauntered towards the elevators, even the ones with their wives and girlfriends which made me feel empowered. I stepped out of the elevator and Natalia was waiting for me. "Greetings Miss Riley, this way please." "Hi Natalia, good to see you again." "Likewise," she said. I followed her back to Steve's huge office. As soon as we entered Natalia grabbed me and began kissing me deeply. I let her tongue probe my mouth for a while, her lips were soft. I wanted to give Steve a good show. I opened my eyes and realized Steve wasn't here. "Natalia, where is Steve?" I asked. "Steve's meeting was out of the country," Natalia said coyly. "So why am I here?" I questioned with a puzzled look. "I want to make the sex with you again," she said in her accent. "Without Steve?" I asked. "Yes as you saw he is a pathetic man with a pathetic penis," she said accompanied with a disappointing look. "I don't think he would approve," I told her. "He will not approve unless he gets to watch but he is not here. You have a deal with him but, things could always fall through," Natalia said. At that point I didn't have a choice; I needed, and wanted this show. It wasn't a subtle point that Natalia was trying to make. "Ok Natalia," I said. I knew she had me where she wanted me. In the last few days I'd seen hems of skirts and dresses go up and down more than the stock market. Mine was going up again. We moved over to the huge desk and Natalia hopped up onto the desk. She was wearing nothing under her tight dress. She spread her legs and pulled me to her slowly. Her perfume filled my nose with a heavenly scent. Reaching down into my panties and pantyhose she untucked what she was looking for. She took her time to massage my erection which was already ready. I wasn't the largest but probably seemed a definite improvement from Steve. Her calling him pathetic made me smile. This time I had those big hazel eyes looking right through me. I had clearly misjudged her. She knew what she wanted, and how to manipulate to get it. As of late I was the one in charge during sex. Even if I allowed someone else to think they were in charge, I really knew that I was. At this moment I clearly wasn't in the drivers seat. She pulled me all the way into her by the waistband of my pencil skirt. Natalia was moist and warm as I slid inside of her warm tunnel. We simultaneously let out small approving moans. She began unbuttoning my blouse and untucking it from my skirt. She freed my right breast and began sucking my nipple. Her hands grabbed two handfuls of my J-Lo style ass that her husband paid for. I began to move in and out slowly. We had no one directing us this time. She had now liberated my other breast and had a handful of each. Her face was full of amazement and wanting. She was handling two big brown breasts, with a dick inside her. My hands were holding her ass and squeezed with each thrust into her wet pussy. One of her stilettos hit the floor behind me. I turned towards the door thinking someone might be coming in. Natalia turned my face back to hers, biting my bottom lip. Her legs locked around me as I could feel she was nearing her climax, I was nearing my moment as well. I felt her vaginal muscles contract as she released with a low moan. With the few minutes I knew I had before my release I repositioned. I put her now lone stilettoed foot atop my right shoulder. I reared back and began hammering as hard as I possibly could. I pulled out of her and squirted my load on the carpet in front of the desk. The ride home was spent thinking what the hell did I get myself into. I didn't know if Natalia could be trusted, I hoped she could. With Steve as an enemy I could go from two shows to none. I was definitely over a barrel, and Natalia had me there, not Steve. Over the next few weeks my agent had negotiated the terms of the new show with Steve. I had been waiting for the other stiletto to drop. The network was ready to roll with it, I would be airing immediately after Gigi's show. Natalia hadn't talked which was great. I was worried what else she may have in store for me. Steve had set up a celebratory dinner at his house. I didn't know what to expect but I was going to find out soon enough. During dinner Steve excused himself from the table. Natalia had begun to tell me the dynamic had changed between her and Steve. I didn't know to what extent until we got up to the bedroom. Steve was there fully "Dressed", he had to be the worst looking crossdresser I'd ever seen. He was a far cry from my original foray as Riley. Some men just weren't meant to be women, he was one of them. "Riley, my darling husband has agreed to be my sissy boy as of late," Natalia said as she beamed. "I see, and he is quite terrible at it." I snickered. "He will improve but for now he will do. Isn't that right sissy boy?" Natalia said to him. "Yes ma'am," he clammered. It was quite the sight to see the high and mighty Steve in this position. Natalia motioned for me to have a seat on the sofa. She went into the closet and returned with a thick black dildo that looked a foot long. I had a front row seat for this show. Natalia gave me a wink as she circled Steve like a predator. I was eager to see it all happen. The thrill of seeing a powerful man broken had my own juices flowing. She laid Steve across the bed. I had full view of his ass as she instructed him on all fours. She hiked up the too small dress he was wearing and pulled his lace panties down. Steve's facial expression was outright giddy. It wasn't for long; Natalia whacked him across the ass with the long rubber dildo. His pale white ass turned bright red as she continued her onslaught. I stood and came closer to get a better view. Looking down at Steve was exciting. It was my first experience witnessing someone else's humiliation and I liked it. Steve's makeup was clumsily done, the foundation uneven, the lips poorly done and the eyes were a complete mess. His dress was a poor fit and didn't suit him at all. I later learned it was done intentionally, Steve got off on humiliation. The tirade of insults Natalia spat made him ecstatic. She called him a poor excuse for a man and a sissy boy which was true. The more small limp dick insults she shouted the harder he got. It reminded me of the days when I couldn't get it up unless I was Riley. I was fully erect at this moment tucked into my tight dress. I went from a man to a crossdresser to a shemale in no time at all. What was next for Riley?, I didn't know what the future would bring. At this very moment Natalia was handing me the big black dildo and offering Steve up. Natalia applied the lube as Steve arched his back in anticipation. I couldn't believe this one eighty that I didn't see coming. I moved behind him to get a better angle. I wasn't gentle with the insertion as I rammed it in. Steve's moan of enjoyment let me know this wasn't the first time. It was amazing to see how Natalia had turned the tables so quickly. I started to inch the dildo in deeper with each pump in. While I pumped in and out Natalia began her verbal lashing of her husband. "Do you like that you ugly sissy?, she yelled. "How does it feel? You're a pathetic ugly sissy boy with a little, weak dick," Natalia barked. I could tell her words were coursing through him. He was loving it, as he began to thrust back onto the dildo. Natalia continued, "You are a sad excuse for a man and a sadder looking sissy. Riley is so beautiful and you're a fucking mess. Look at your tacky makeup and your crappy dress. You will have to get much better to stay with me." As the last words escaped her lips, Steve's load escaped his little manhood. This infuriated Natalia as she took the dildo from my hands. She took it out and ordered Steve up onto his cheap heels. His stood looking like a sad heap while pulling his dress down. " I will show you how to please me," Natalia told Steve. Natalia unzipped her dress and stepped out of it. Her heavy bosom seemed to overflow her bra. She pulled my dress up and pulled out my member. She laid back on the bed and motioned for me to come to her. As I got up into the bed and crawled towards her I looked at Steve. He was beside himself with glee. Natalia grabbed my cock and inserted me in. She was warm and tight as I started to pump but stopped. My panties and hose around my hips felt restricting. I took them off and reinserted into Natalia. I was able to fully get into her balls deep. We grinded together in unison slowly, watching Steve's reactions. Her pussy was just as good as our second go round on Steve's desk. Undoubtedly he knew about that escapade and was ok with it. Natalia releasing my breasts brought me back to her, looking down into her eyes, I knew she enjoyed her new role. Steve's moans increased in volume and depth. He was now stroking himself with my pantyhose quickly. I knew his load would be soiling them shortly. It seemed he and Natalia released in unison. I came shortly after with my breast almost smothering Natalia. I sat up and began putting myself back together. Natalia lit a cigarette and looked down on the crumbled heap that was her husband. Steve lay in an exhausted state on the bedroom floor. "This was quite an evening, I would like to thank you both. You were a very generous host," I said to Natalia. "You are quite welcome, Darling. We will be doing this again, Yes?" Natalia asked. "Yes we will," I said. I knew what a refusal would get me, No show. I slipped on my heels and stood to leave. "Good night," I told them. Natalia sat up. "Darling you are forgetting something." "Am I?" I asked. "Please honey, you can not leave without putting your pantyhose back on," she said. Her tone of voice inferred that it was a demand rather than a request. I knew what I had to do. I walked over and picked up my black sheer to waist mess. The look on Steve's face said, I am losing a souvenir. They were a globby mess of Steve's juices. Putting them on one leg at a time I could feel his sticky mess on my skin. I lifted my dress and pulled them up my hips and over my ass. The majority of his warm glob was wetting my ass. I pulled down my dress and walked towards the door. I looked back to see Natalia reveling in my humiliation. Steve was not the only one now at her mercy. I hoped she couldn't see what I was feeling. Riley was bitten by the humiliation bug.