tagTransgender & CrossdressersDiva Las Vegas Pt. 02

Diva Las Vegas Pt. 02


This is the second of a three part series. Please read Part One first for the character's backgrounds.


The story so far: Hal and Rona are a married couple from Kansas who lead fairly mild, vanilla lives. Rona has an obsession with watching Ru Paul's Drag Race on TV. Hal enjoys it too. He really loves how excited Rona gets when she watches it. For their third anniversary, Hal and Rona go to Las Vegas during the big Trans convention called "Diva Las Vegas." They take in a drag show and they meet three new friends, two trans women and one cis gender woman (Janie, Mary-Margret and Anne) which gets Rona worked up. Her sexy alter ego is named Roxanne who she becomes when she wants to get wild. Hal submits to playing a femme role for Roxanne as they explore some new sexual territory. After an incredible night of sex, Hal passes out. Rona, or rather Roxanne tells him that she plans to continue her game.

The story is told from Hal's point of view.

It was the morning after our first night in Vegas. I slept like a baby. I was sore but satisfied. I had sweet dreams of the night before as my wife Rona, had become her sexy alter ego, Roxanne. She forced me to submit to her will. I eagerly played along. She started calling me Holly and referring to me as a girl. She broke my anal cherry with a strap on fuck that made me come harder than I could ever remember.

It all happened after going out to a drag show. I couldn't believe what a turn on it was for my wife. I enjoyed it too. Even more arousing for me was meeting Janie, a pretty trans woman and her genetic wife Anne, a busty blonde and their close friend Mary-Margret, another trans woman. They were all from Canada, I remembered. I had drank a lot and was still a bit fuzzy but it all came back quite clear. I finally pried my eyes open and saw the clock, reading ten-thirty AM. I had to pee so I hoped out of bed still naked from the night before. I suddenly noticed that my wife wasn't in the room. I was alone. There was a food tray on the table however.

After taking care of business, I opened the food tray and ate some of the bacon and toast and drank a strong cup of coffee. Only then did I find my phone and sent Rona a text message asking where she was. She replied back in a few seconds, "Shopping, back soon." That gave me time to enjoy my coffee. I picked up the flyer that I received from Janie the night before. It was an itinerary for all the Diva events going on all week. I noticed that one event was circled for that same day. It appeared to be a big welcome cocktail party and featured Ru Paul herself as the MC. It appeared that my wonderful wife was making plans to go to the event. I had a lot of fun the night before and was definitely interested in going to this new party.

Eventually Rona showed up back at the hotel. My cute, pixy wife was wearing cut off jean shorts and a tight blue tank top. She came baring several shopping bags. I didn't expect such a big shopping spree on the first day but if it made her happy then it made me happy. She put the bags down and came in to hug me. She placed a big kiss on my cheek. "What did you buy honey?" I asked casually while sipping coffee.

Rona squeaked with joy. "You won't believe what I bought you sweetie. I can't wait to see you in everything," she burst with excitement. I looked at all of her bags and noticed that they were from ladies shops. I wondered what she could have possibly bought me. The first thing she pulled out of a bag was a white dress. It was a made of a silky material with a scoop neck line and had a built in cream colored bodice. The hemline looked rather short.

I stared open mouthed at my wife who was grinning like a Cheshire cat. "Well, what do think?" she asked after my endless silence.

"You want me to wear that? You want me to wear a dress?" I asked both confused and excited.

She paused for a moment but still held up the dress. "Well ya silly. Of course I do. I mean, after last night and everything. We're going to be girlfriends. You have to look the part, right? Don't you want to?" she persisted. I continued to pause, not knowing what to say. "You promised anything, remember?" she reminded me with a slight tone of anger beginning to rise in her voice. Her big round blue eyes, enlarged by her big glasses, pierced through me.

I stammered, "Ah yes, I promised. I know. I'm just a little shocked and also definitely scared. This is a big thing. I don't know if I'm ready. You want me to go out wearing that? It's lovely, don't get me wrong but what would I look like in that?"

My wife smiled in relief. "There's only one way to find out. You're going to try it on. Not only that but look what else I got you," she encouraged me as she drew out a pair of cream colored high heel sandals. She continued pulling items out of the bags, including beige stockings, fancy lace underwear from Victoria Secret, makeup items and other stuff. "I thought a nice virginal white was a good color for you since it's your first time."

I blushed but was enthralled by all the sexy clothes which were all for me. I started feeling the fabrics with a gentle touch. It was getting me excited. Rona paused at the final bag and made a huge smile. She pulled out two flesh colored silicon pads which looked like chicken breasts. "Voila, instant boobs," she teased. I felt the gel like pads which had a pliant consistency of a breast. She paused again and announced, "...and finally, the capper. I imagined you as a long haired blonde. Ta -da!" Rona pulled out a long silky wig made of light blonde hair. I was a natural blonde anyway so it made sense.

I stroked the beautiful hair which curled a little at the ends. It was amazing. Suddenly, I was eager to find out what I would look like. I was about to put it on but Rona stopped me. "Not yet babe. Step number one. Into the bath tube and shave everything below your eyebrows, and I do mean everything," she ordered. She really emphasized that last word too. She snatched the wig out of my hands and pointed to the bathroom. "Let me know if you need help with the tricky parts," she added with a devilish Roxanne grin.

I would definitely be taking her up on that. I trusted her completely. Besides, she shaved her own crotch all the time and was an expert in my opinion. The bath and the shave took a while and I did get Rona's help. I had a hard on the entire time and she teased the hell out of me. When we finished my full shave, Rona rewarded me with a great blow job. I came in record time and she eagerly swallowed most of my load. She saved a mouthful and placed her mouth on mine. As we kissed, she passed my cum back to me. I took it and swallowed it down as we made out. Rona approved and giggled at my submissive obedience. "Good girl Holly," she complimented. She had called me Holly the night before as she fucked me like a girl.

After drying off, she had me cover myself in a moisturizing lotion that she had just bought. My legs were so silky smooth. I had never imagined how incredible that felt. I was beginning to see the appeal of the others like Janie and Mary-Margret to this type of lifestyle. I came out in a bathrobe and my wife had laid out all my new clothes. "Okay, let's start with the underwear. Panties, bra, corset, garter belt and slip." She helped me with the foreign items. Everything was white. The corset was uncomfortable but it had an effect that drew in my waist line and made my hips and ass appear larger. The silicon pads made me appear to have a bust.

Rona examined my crotch in the silky panties. She didn't look happy. With hands on her hips, she said, "That won't do. You'll have to tuck that up between your legs." She was pointing at my cock bulge. It did look odd and un-feminine. I reached down and lowered my panties a little. I took hold of my cock and balls and pushed them back between my legs. I had heard enough about "tucking" from watching Ru Paul's Drag Race to know what to do. I pulled my panties back up and pressed my thighs close together. I even posed like a woman model.

Rona smiled approvingly. "Much better Holly," she stated. "Now for the stockings," she continued. Rona showed me how to roll up the stocking first and place it over the toes, then roll them onto the foot first and up the leg. She helped me fiddle with the garter attachments of which there were three on each leg. When I looked down, I noticed the fine quality of the stockings. They had that vintage look with seams up the back and darker welts at the top of the thighs. Then came the dress. Rona zipped me up in the back and fussed with the fit. She wouldn't let me look at myself in the mirror yet. She had me sit down and she strapped on my shoes. They were open toe with dainty cream straps. The back came up the heel to my ankle where an ankle strap waited. Rona buckled it up and then did the other foot. Finally, she put on my wig. She adjusted the fit and teased it out with her fingers. "Okay Holly, stand up and turn around," she commanded.

I gingerly stood up and tried to find my balance in the four inch heels. "Stand on your toes and arch your back. Keep your head up. Good girl," she encouraged. I finally was able to turn around without falling. I looked in the mirror and was amazed. I knew I didn't have the most masculine physique in the world but the image looking back at me was screaming woman. Other than my plain face which had no makeup on, I looked very feminine. "You see Holly. You were worried about nothing. You look incredible. A little makeup and you'll be ready for Ru Paul's cocktail party tonight. Now, you need to practice walking in those shoes."

My wife gave me instructions on walking in high heels. She made me practice walking all around the room. I got pretty comfortable after an hour or so. Then she taught me how to dance while wearing them. That was trickier but I was a fast learner. I was gaining a lot of confidence in the hotel room but that was just with Rona and I. Going out in public was another story. My wife retrieved the card that Janie had gave us the day before and gave her a call.

I listened into the conversation as my wife spoke for us. "Hi Janie, this is Roxanne. Remember my husband Hal and I from the show last night?" she spoke. "Good, good. It was great meeting y'all too. Listen. We were wondering if y'all were going to the cocktail party tonight? You are? Great. My husband and I are going too. We were wondering if y'all wanted to meet up for dinner before that and then we could go together?" she asked. "Great, that's great. I'll make us a reservation. What do y'all like to eat?"

With company for moral support, I felt even more confident. If I wasn't the only cross dresser at the table, I wouldn't feel like everyone was staring at me. My wife had read my mind and knew it would help. She booked a table for five at a sushi restaurant. She had me take off the dress and wig but I stayed in the slip. Rona took a shower herself and began getting herself ready. She had bought new clothes for herself too. Although she wore sexy black panties and a bra. Her outfit consisted of tight black trousers, a white dress shirt, white vest and a black tuxedo jacket. It was very much like Marlene Dietrich.

Rona helped me with my makeup next. It was more like I sat there and she painted my face. I listened to her as she told me what was going on but I just let her do her thing. There was a layer of concealer and then foundation base. Then there was the eye liner and eye shadow. Then there was blush and lip liner. Finally she put on mascara and lipstick. After me, she did herself up. Rona didn't wear much makeup herself as she wanted me to look more feminine than her. Her hair was already a shorter length with her pixy style. She ran some product through her hair so that it stiffened up in place. It still had a feminine style to it but just a little less. She then put on some black socks and a new pair of oxford shoes with a low heel. To cap it, she wore a white bow tie. Even in men's clothes, my wife looked smoking hot. I put my dress back on and my wig. Arm in arm, my wife and I went out as Roxanne and Holly.

We met up with our new friends, Janie, a trans woman from Toronto, her wife Anne and their friend and traveling companion Mary-Margret, another trans woman at the restaurant. They were all surprised to see me dressed up as a woman for the night but they were all very complimenting. Anne was of a similar mind to my wife. She had worn a white blouse and black trousers although hers were feminine in style. She had the buttons open to reveal her insane cleavage. Janie and Mary-Margret wore dresses of course. Mary-Margret wore a curve hugging black dress with silver buttons up the front and a white collar. She wore it open to show off her cleavage which had a strand of pearls adorning it. The sleeves of her dress were translucent nylon bell sleeves. She wore her red framed glasses, black nylons and black stiletto heels. The outfit complimented her strawberry accented red hair. Janie was dressed in a sleeveless, little black dress of satin material that clung to her hips but had a delicate flare at the bottom hem. She wore black fishnets and hot looking lace up high heel ankle boots. Her green eyes sparkled and her curly red hair was coifed out perfectly.

Our new friends couldn't say enough nice things about how my wife and I were dressed. My wife, using her alias of Roxanne, introduced me as Holly. From that point on, everyone called me Holly and I never once heard anyone mutter the name Hal. I felt incredibly confident as I had seen my reflection and there seemed to be no trace of a man at all. The makeup really helped. My eye shadow was really dark and my lips were a ruby red. We had even done my fingernails.

The five of us had a wonderful sushi supper. We drank a lot of wine too. Over dinner we shared a lot about ourselves and learned a lot about our new friends. We discussed our jobs and homes and so many other things. I could tell that my wife really enjoyed the company too.

After dinner we made our way over to the convention hall that was hosting the party. I felt even more comfortable as the majority of men in the crowd were not dressed like men. In fact, more women, like my wife and Anne, were dressed in men's clothes than men were. The party itself was quite fun. There was so much booze and there was music. Of course Ru Paul herself made an appearance as the hostess. I received so many compliments for my look that I felt on top of the world. There was dancing and the five of us stuck together most of the night, dancing with each other mostly. I was asked by a manly man at one point for a dance and I accepted. He was over six foot tall and over two hundred pounds. I felt small and vulnerable as he took charge of me while we danced. Afterward, he complimented me and gave me a kiss on the cheek. I blushed like crazy at the strange feeling I was getting.

My wife teased me endlessly about that for the rest of the night. She spent a lot of time dancing with Janie, Mary-Margret and mostly Anne. Anne seemed to really love the Marlene Dietrich outfit. She and Rona seemed to do a lot of talking whenever they danced alone. They also seemed to be getting very close to each other. They did a lot of touching of one another. I was getting a similar treatment from Janie and Mary-Margret. Their hands touched me a lot and during some of the dancing, their faces got close to mine. At one point, Janie simply leaned in and kissed me. I didn't freak out or back away. I simply kissed her back. I looked to my wife who smiled approvingly. After that, we all got kissy with one another. I kissed Mary-Margret. Anne kissed Rona. Rona kissed Janie. Anne kissed me. It went on an on like that.

When I eventually ended up back with my wife, we danced slowly and she kissed me softly. She whispered in my ear, "Anne asked us back up to their suite for a little after-party party. What do say Holly? Want to go play with our new friends?"

"If Mistress Roxanne wants to play then so do I. Hell yes!" I responded. She kissed my full on the lips and slid her tongue down my throat. After a brief stop at our room because Rona said she need something, the five of us were heading up to our friends' suite. They were staying at the Flamingo too.

Once in the room, Mary-Margret produced a bottle of bubbly that was on ice and popped the cork. She poured drinks for us all. Janie put on some music so we could all resume dancing in a more private setting. The mood returned to what it was at the party. The touching and kissing started up again. Anne giggled and pulled Roxanne aside. She whispered something to my wife who nodded her head in agreement. The two cis gendered women sat down on the sofa and watched the three of us continue to dance and frolic. They sipped their drinks and watched the show. Looking back at my wife, I saw the look in her mischievous blue eyes and knew that she wanted to see a real performance. She licked her lips and I was sure of it. She was in full Roxanne personae.

I took hold of Janie by the waist and pulled her close to me. I put my mouth on hers and forcefully kissed her. Janie melted in my arms. She kissed me back with pure lust. Her leg rubbed against mine. As we kissed, I felt breasts pressing into my back. Then a hand grabbed my ass and squeezed. A mouth nuzzled my neck and kissed it. It was Mary-Margret. She and Janie made a sandwich of me. Four hands groped my body and two mouths explored me. I was turned around and felt Mary-Margret's plump lips press onto mine. As we made out, one of them began unzipping my dress. I felt a sudden twinge of panic but the reassuring kisses and the booze kept me at ease. I didn't resist and my dress was soon being peeled off of me. As soon as it was off, Mary-Margret put her hand over my panty covered crotch. She squeezed my cock between my legs and it popped back out in front of me. It was hard and straining the delicate white fabric. Janie was behind me and she grasped the waistband of my panties and slowly lowered them down. She went all the way to the floor and helped me step out of them. My cock was free and it grew to its full six inches, standing straight and proud out in front of me.

Mary-Margret spun me around so that I was facing Janie who was still down on the carpet on her knees. My stiff erection slapped her right in the face. Janie giggled and opened wide for me. Suddenly, I felt her mouth, the only other mouth other than my wife's wrap around my meaty cock. I looked down at her and Janie was looking back up at me with her pretty green eyes as she sucked on my cock with her red painted lips. Her tongue gently licked all around the head of my penis getting it wet and heating me up even more. I put my fingers in Janie's wavy red locks and guided her head as she bobbed on cock.

I looked around to see how everyone was taking it. Anne seemed to be enjoying the show as she sipped her champagne while she sat cross legged. Her free hand was caressing her own breasts on the inside of her blouse. Her sky blue eyes were fixed on her husband/wife giving me head. She seemed to be used to it. It was certainly not a first for them. My wife's eyes were riveted on me. I could see her getting flush like she did whenever she was super horny. Her legs were open and one hand was already busy rubbing her pussy through her trousers. She was almost drooling. Mary-Margret meanwhile, was unbuttoning her dress reveling a sexy black slip underneath. Soon she was dressed just like me, in a slip with garters showing, stockings and high heels. Only hers were black compared to my white slip and beige stockings.

Janie had managed to open her throat and take my entire shaft deep. Her lips pressed against my balls and pubic bone. I could feel the head of my cock swelling inside her hot throat. I took deep breaths so that I wouldn't come too quickly. It was tough but the earlier blowjob from my wife and the sex filled night before gave me increased stamina. Mary-Margret came over to us and joined Janie on her knees in front of me. "Janie you greedy slut, give me a taste of Holly," she demanded with a wicked smile. Janie reluctantly popped my dick from her mouth. It was covered in stringy saliva and red lipstick. Mary-Margret eagerly took hold of it and wrapped her juicy red lips around it. She sucked on the head hungrily while massaging my testicles with one hand and pumping the base of my cock with the other.

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bytgirl_Mary© 5 comments/ 24099 views/ 23 favorites

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