tagTranssexuals & CrossdressersYou Got the Part! Ch. 02

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?"


"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."

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