Ronnie: Womanless Beauty Pageant

Ronald/Ronnie had come to terms with her femininity and had left home to attend college. Wanting to have her own titties she began taking low dose female hormones. By the end of her first semester she had respectable breast buds and womanly nipples. Like most college students Ronnie was in need of money. She and her titties enter a Womanless Beauty Pagaent with a $1000 first place prize! In the process Ronnie finds an Angel. (Part 2 of 3 parts)

Question: “What’s more fun than having titties and has more income than a traditional job? A Womanless Beauty Pagaent!”

Recap of “Ronald: Evolving into daughterhood” (part one)

Ronald/Ronnie had come to terms with her femininity and had left home to attend college. Wanting to have her own titties she began taking low dose female hormones. By the end of her first semester she had respectable breast buds and womanly nipples. Like most college students Ronnie was in need of money. She and her titties enter a Womanless Beauty Pagaent with a $1000 first place prize! In the process Ronnie finds an Angel.

Question: “What’s more fun than having titties and has more income than a traditional job? A Womanless Beauty Pagaent!”

As a struggling student I was always looking for ways to earn additional income. I picked up odd jobs whenever I could. I was ecstatic when I found an opportunity to make a quick $1000. It was also an opportunity for me to indulge in socially acceptable cross-dressing! All I had to do was win the Womanless Beauty Pageant!

The pageant ‘job’ would also allow my alter ego, Ronnie, to emerge from seclusion; I was excited and apprehensive at the same time. Third place paid $500. I decided that if nothing else the experience would be worth the effort. It was an excuse to become pretty; the money would be nice too.

Two weeks prior to pageant orientation and preliminaries I got serious.

Based on a recommendation from a girl like me I went to a local LGBTQ friendly cosmetology and hair salon called the “Curls 4 Gurls Rainbow Salon”. I explained to the stylist, Carole, about the Pageant and the $1000 first prize I desperately needed to win. I tipped her $25 before she began her efforts. Carole smiled and said, “No problem Precious, I’ll take extra care in making you very pretty; your boyfriends will be proud to take you out.”

Before beginning, and at Carole’s suggestion, I allowed her co-worker to shape and clear coat my nails in anticipation of a full manicure being done just prior to the main event. “May as well get started on them now; we’ll do the ‘real thing’ just before the contest” Carole said. The nail girl smiled at me and said, “You do a fair job with your nails, Missy. It looks like you shaped you nails recently.” I nodded and said, “It’s been awhile since I gave them the attention they deserve.”

Carole cut, shaped and layered my long hair to an even below-the-shoulder length; she used a mild body wave permanent to create a soft fullness and lift; she gave me attractive highlights to enhance the overall effect of her creation. Carole thinned and femininely re-shaped and arched my eyebrows.

When I was turned to face the back wall mirror I was well pleased with the results; I saw a pretty Princess looking back at me. I wondered what a bit of makeup and lipstick would do to enhance my feminine image. Carole had the same reaction to her finished product. Standing behind me we looked at our reflection in the mirror, made eye contact, and said nothing; our silence spoke volumes.

As if reading my mind Carole reached into her purse, retrieved a lipstick and some mascara and held them up in our reflection. Carole held her head at a quizzical angle, slowly waved the cosmetics and asked, “Shall we see if Ronnie could make a good showing in the pageant?”

After a moment’s hesitation I nodded my head ‘yes!’ I closed my eyes and waited for Carole to work her magic, after all she is a cosmetologist, right?

Carole did what needed to be done. Carole added eye liner, evening eye shadow and multiple coats of mascara for impact. Those items added to my feminine look; my eyes were alive! She chose a lipstick color that was right for my complexion. Without asking Carole gave me a light spritz of Chantilly Eau de Perfume; a classic feminine scent.

Carole’s nail assistant spoke up, “I hope you don’t mind but I swapped out your clear coat polish for a subtle beige that better suits your new look; next time we should try a red or maybe a coral.” I checked my shaped and painted nails and smiled broadly. “No, I don’t mind at all; you gave me exactly what I needed.” I was pleased at the way things had worked out. I most definitely did not look like a feminine man.

I paid my bill, left another tip and said, “Thank you for being so nice and understanding to me.” Carole smiled and said, “We girls need to stick together, Sweetie. When you return for a follow-up appointment be wearing something pretty; Levi’s and lipstick don’t look good on you!” Carole kissed me on the cheek made me promise to return a day of two before the finals for a touch up on my hair and nails.

I got in my car and decided to drive around town for awhile like I used to do with mom and let my thoughts run wild; driving always gave me time to think.

The Pageant was weeks away! I hadn’t considered how the college or friends and neighbors would react to seeing Ronnie rather than Ronald. ‘How in the world am I going to explain my new look from them?’ At least I was happy and content.

Augment, update and replenish

The Pageant was the perfect excuse for me to expand and update my wardrobe and cosmetics. I made a mental list of things I’d need. I already had panties and bras so makeup and nail polish remover, cotton balls and mascara topped my list.

Time passes - Day 1 - Pageant preliminaries and orientation were quick

The Womanless Beauty Pageant began with 18 entrants and required a $50 entry fee per “woman”. Today’s preliminary competition would reduce the crowd of contestants to 10 finalists. We had been told for the preliminary to keep things simple and to save our very finest gown or dress for the final event. Hair, makeup, poise and hitting our marks would be the key factors today. We were also told there would be a pre-final’s rehearsal before the Pageant.

I arrived at the pageant site with my hair, eyes and makeup looking very womanly. I gathered with the other contestants near the stage podium and received the obligatory briefings and pageant rules; I completed the required forms and releases. Glancing around at the other contestants I checked out my competition.

We were all in basic girl garb but with minimum makeup & low heels. Today was to be the first cut of contestants. Several of the “girls” were very believable and had mannerisms that suggested they weren’t amateurs or they weren’t men; they carried themselves differently. I noticed an attractive girl in the briefing. Her name was Angel and she seemed to fit that profile.

Contestants were required to walk single file around a two lap judge’s evaluation course as medium tempo music played. We had specific places where we were required to stop, do a slow 360 turn and then continue gracefully walking to our next mark. ‘Girls’ that couldn’t hit their marks or who didn’t meet a basic believability rating were thanked and excused. I felt sad for those that were thanked and excused by pageant officials.

And then there were ten

Myself, and the girl named Angel, were one of the girls told to return. I was happy but nervous that I would be in the finals; life was getting very serious and perhaps complicated.

Before leaving the pageant facility we ‘girls’ that had passed today’s test were briefed on what the routine would be on pageant day. We were assigned a pageant partner and told there would be a pre-final dress rehearsal two days before Pageant Day that we had to attend. There were dressing rooms where, on rehearsal day, we could bring and leave our Pageant clothes and other necessities prior to the big event.

To overcome a lack of dressing rooms the final 10 Pageant entrants had been paired off and assigned a shared dressing room that could be used until the pageant was over. The rooms were adequate but not very plush; two chairs, a fully stocked makeup vanity with bench, large mirrors, makeup removal pads, clothes rack, desk, sink, etc. The Pageant also provided a small dorm refrigerator stocked with bottles of water. Gender neutral restroom facilities were nearby.

Rehearsal

Contestants had no problem in helping each other; it was a “you hook my bra and I’ll hook your bra” camaraderie.

Luck of the draw

It was luck that I had been randomly paired with the perfect Pageant partner; the (wo)man named Angel. Unlike me Angel had been a contestant in, and had photographed, several similar contests; he owns and operates “Angel’s Boudoir & Fetish Photography.” Angel said that being a participant in Womanless Pageants generates customers and is why he enters them. He makes a very passable woman.

Upon being paired up Angel had asked me and the other contestants for permission to photograph us; I signed a release. I think Angel’s cross-dressing and pageant entries are more than just a hobby. Angel and I became instant friends.

Dressing room

Angel and I were in our dressing room getting ready; I was more nervous than Angel. He was fiddling with a new hand sized digital camera. He aimed it at me and took a picture. “I’m working on a new project and need photos of pretty boys like you.” I turned sideways, struck a pose that showed off my fake breasts and Angel took another photo. Angel taking pictures didn’t bother me at all.

“Angel, would you zip my dress up please?” I asked. “The damn zipper is stuck.”

My dress hung loosely as I needed help with the zipper; it reminded me of my punishments. Angel had watched as I put on my bra and hooked it effortlessly with my hands behind my back. In fact he took a few candid photos of me putting my bra on. Like a woman does I nonchalantly shrugged my shoulders and wiggled my small but growing titties into their proper place; I was still using breast augmentation forms until my breasts fully developed.

Angel snorted and asked, “It looks like you’ve put on a few bras in your lifetime; is that correct?" He labeled those photos ‘Cross-dresser Hooking His Bra’.

“What?”

“You look much too comfortable and relaxed for a boy that’s never worn a bra before. Not only did I notice your involuntary shoulder shrug we all do to get our bras in place I also noticed your perky adolescent titties.”

Bra fit test

“They may be small now but they are all mine; they are a work in progress! Will you please zip my dress” I asked again.

“Before I zip up your dress let me check if your bra fits right.” Our dressing room door was shut.

Standing behind me Angel tugged on my bra straps and said, “We need to shorten the right strap a bit.” Angel expertly shortened the stray strap about a ½ inch. “There, your bra looks even but we need to check one more thing.”

Angel put his hands into the open back of my pageant dress, reached under my armpits and into my bra. I could feel Angel’s body heat in his hands. He gently cupped both of my nascent but eager breasts to “confirm size and fit.”; they filled his hands. I’m sure it was like feeling up a 12 year old girl.

It was not an accident that Angel gently rubbed my raised nipples in a sensuous manner. He was either looking for something or sending me a message. I gave an involuntary soft moan of pleasure in response to his touch; my nipples grew firmer; I thought of Dan and did not resist Angel’s obvious advances.

Embolden with my non-response Angel gave each of my breasts subtle, deliberate and prolonged caresses. Angel’s touches felt so very nice; so excitingly forbidden. I felt a stirring in my penis. I regretted being in such a public place. I thought of Dan.

I’m an inspiration

Angel was pleased and inspired on several levels: both of my nipples immediately grew rigid in response to his touching; and I had responded with a moan of delight rather than a scream. Most important was that I had not pulled away, struggled or yelled. I stood motionless and unashamedly wished for more. Angel’s fondling of my developing breasts had me transfixed; they were sensitive and responsive; my breathing became more rapid.

Speaking softly from behind Angel said, “I can tell your bra band is loose. It wouldn’t have been so easy for me to cop a feel if your bra fit better. Let me tighten it for you; one or two notches should do the trick; with a bit of luck it should also give you a bit more cleavage. Do you mind?”

It took a moment for me to compose myself. I softly replied, “No, I don’t mind; I don’t mind at all; it’s been a long time since a man has touched me.”

“A man has touched you before?” Angel asked.

I pressed my butt gently backwards and made contact with Angel’s crotch; I rubbed my butt invitingly against his front; I could feel “it”; I was like a bitch in heat. I wanted to tell Angel to not stop; perhaps my butt rub did signal ‘don’t stop’. Maybe it was Angel’s lucky day… perhaps it was mine.

My boldness startled me and I immediately stopped acting like a truck stop slut; the situation became awkward. Angel withdrew his hands.

I cleared my throat, took a breath and apologized, “Oh, Angel, I’m sorry about acting like such a tramp; my libido from a prior encounter must have kicked in.” I nonchalantly inserted my silicon enhancers where they needed to be and acted like nothing had happened.

Change of subject

“Ronnie darling, we really need to get together so we can finalize your pageant debut. Bring a dress or two, and your favorite panties, to my place so we can see which looks best for the Pageant.”

“We need to make your eyes prettier and I need more photos of you. Have you heard of eyeliner and eye shadow? Have you heard of ‘showgirl’ eye makeup?”

“I don’t have much experience with eye makeup.” I thought about Carole’s skills.

“I do have eye makeup experience. I even have a larger pair of professional silicon bra inserts that you can have. Every girl should have at least two sets. The nipples look real and the tits have a perfect feel to them but we all know that nothing beats kissing the real thing."

Angel smiled, I smiled and I blushed.

“When’s a good time to meet?” I asked. Angel didn’t reply but I could tell he was thinking.

A secret shared

Before exiting the dressing room, almost as an afterthought, I said, “I never did answer you about having worn a bra before or having been touched by a man. Yes, I have worn a bra before. In fact I wear panties and stockings whenever the mood suites me; they make me feel special and complete me in an odd way; I wear them under my boy clothes.”

“I’m pretty sure I knew that already” said Angel.

Touched by a man?

“I was never touched by a man; I was touched by an older boy when I was a young boy and then by a high school classmate most recently; he stirred me in ways I hadn’t imagined. It’s so confusing; I’m not sure what I should do and I’m not sure what I should allow myself to do. I was a willingly participant both times.”

I felt a strong sense of relief of having shared my secrets with an understanding friend; a new friend that lived nearby and knew about eye makeup! I chuckled inwardly at the thought and made a mental note to pick up a bottle of wine or two if Angel and I were to get together.

I leaned close to my vanity mirror to touch up my lipstick. Angel managed to capture a few quick photos of the exact moment that my lipstick touched my lips. “I think I’ll call these photos ‘Boy Getting Pretty’” Angel announced. His comment made me laugh and when I turned to face him he snapped a third photo of me smiling when I had just finished with my lips. Of course my lipstick matched my nail polish.

I stepped from the dressing room and back into the main convention room where the pageant rehearsal was to take place.

We made it through rehearsal

Upon entering our dressing room after the rehearsal I took a glance into the floor length mirror, smiled and admired how pretty I looked and felt; I saw a pretty woman looking back at me. I was glad I had entered the pageant. I wondered if I should invite mom or Dan to the final day.

I changed out of my dress and placed my ‘costume’ in a protective garment bag. I slipped into my boy clothes and like any boy like me I left my bra, panties, stockings, heels and makeup on. Angel was nowhere to be seen. I draped my garment bag over my arm and headed to the parking garage elevator.

Just as the down elevator ‘dinged’ open Angel appeared from a nearby hallway. “Hey Ronnie, congratulations for making the cut.” Angel stuck out his hand as if to shake hands and pressed a tube of lipstick, and a note, into my hand like you’d do with a $20 bill and a head waiter at a fancy restaurant if you wanted a better table.

Angel explained; “I dashed next door to Sephora and picked you up a good luck charm. The color matches your complexion perfectly and is a light enough shade that you can wear it during your daily activities or when ‘when the mood suits you’ as you said.”

I stammered out a ‘thank you’ and could feel an involuntary blush well up in my cheeks. I anxiously asked, “Will I see you before Pageant night?” Flashing a winsome grin Angel said, “Sure, Sweetie, read my note when you get a chance.” I grasped Angel’s note and gift more tightly.

As I stepped into the empty elevator Angel patted me on the butt and said, Take care Princess, stay pretty!” I turned to face Angel in time to see him wink at me and blow me a kiss. “Are you taking this elevator?”

As the door was closing Angel replied, “No, I’ll catch the next one; I need to take some photos for a few clients.” The door closed and I was staring at the androgynous reflection of myself in the polished brass doors. I exhaled deeply in an effort to rid the tenseness of all that had transpired over the last few hours.

During the elevator ride down to the garage I tried to make sense of what had just transpired.

More than clothes

The elevator door opened and I pushed my deep thinking to the background for now. Opening my car door I hung my garment bag in the back and slid into the driver’s seat. Still a bit unnerved from the day’s events I inadvertently tried to use the tube of lipstick as a key fob. “Damn!” I thought; “I got to slow down and relax my brain.”

I exhaled and fumbled for my real key fob but did not immediately start the car once I had found it. Instead I paused awhile and looked at my new tube of lipstick. Removing the cellophane wrapper I opened the tube and extended it out with one practiced motion. The color WAS perfect. And it smelled very nice.

I reached up, adjusted the rear view mirror and with familiar precision I applied my new lip color; I pressed my lips together as all girls do. The lipstick was, indeed, a perfect shade. I retracted the lipstick and replaced the cap. I read the color on the bottom of the tube: ‘Honey Blush’. ‘I must make a note of this’ I thought. I placed the tube in my shirt pocket.

I was about to put the car in reverse when I remembered Angel’s note. I stared at the note lying on the passenger seat and picked it up. The note seemed to crinkle loudly as I opened it. It read, “I’m sure I’ll be having a wardrobe malfunction soon and I’m sure I’ll need help. Call me.” Angel’s phone number and address were listed. I smiled. I felt a familiar stirring in my groin; I swear I felt my nipples getting hard!

“Oh my God… what have I started?” I thought. I backed out of the parking stall and exited the garage. As I drove towards home my mind was racing. I was gripping the steering wheel intensely. After almost running a red light I tried to relax; I took a deep breath and loosened my grip on the wheel.

Before getting home I stopped at my favorite bodega. I spent more time than planned selecting three bottles of wine; a chardonnay, a Riesling and a blush. Two scented Fleet enemas found their way into my shopping basket. The sales clerk greeted me and commented that I seemed in a very good mood. Actually the clerk said I looked pretty and was in a good mood.

When the clerk scanned the enemas she smiled and commented, “It looks like someone has a hot date lined up.” There was no mention of my feminine hair, heels, makeup or the Honey Blush lip color I was wearing.

Home

I got home and parked under my carport. The apartment manager’s car was parked nearby. Our apartments were both on ground level; I feared Mrs. Johnson trapping me into a long and drawn out story again. I didn’t want to deal with her.

I made my way to my apartment unchallenged, unlocked the door and entered my sanctuary. I locked the door and put the wine in the refrigerator and the enemas in the bathroom medicine cabinet. I changed into a special silk kimono housecoat and panties outfit I fancied and perched myself on the couch in front of the TV. I had serious thinking to do.

It had been a rough day at the pageant practice and also with the ‘events’ with Angel; my subconscious kept wrestling with long suppressed memories and not so latent urges. Were my thoughts urges or were they needs?

My concerns involved a lot more things than the pageant. ‘Why did my libido flare up? Why does Angel make me smile? I also wondered what Dan was doing.’ I decided to wear my special baby dolls tonight. I was having pleasant thoughts about Angel. As I fell asleep my curiosity was growing.

The prelims are over: Dawn of a new day

I leisurely stretched and tried to recall my dreams and decipher their meaning while staring blankly at the ceiling. I remained in bed savoring the feelings my baby dolls gave me while pondering how I got started down the deviant road I’m on. I think it began when I was 11 or 12. Absent mindedly I reached into my panties. My thoughts and my hand wandered. I erupted in a superb self induced orgasm.

I swung my feet over the side of the bed, straightened my baby dolls and slipped on my kimono house coat. I stepped into my gold lame slippers and walked to the kitchen to retrieve my morning coffee. With a cup in one hand and the morning paper in the other I made my way to the couch. I sat down and curled my feet under myself in a natural but feminine manner.

My dreams and memories of the night caused me to put the newspaper on hold. I began staring vacantly to nowhere in particular and let my mind wander. The memories were causing an involuntary arousal. I found myself breathing more heavily and briefly considered indulging in a leisurely morning masturbation session. I shook off what I wanted to do and instead went for a fresh cup of coffee.

I returned to the couch to continue my introspection. Josh may have been the source of my kinks and fantasies but there’s more to my angst; there was a subtle anger I was experiencing. My mind drifted back in time.

I found myself lightly trembling. My repressed memories, desires and weird dreams had an explanation. I had found the source of my anger; a feeling of being abandoned. I went for another cup of coffee.

Things were starting to make sense. The source of my foggy youthful memories and internalized anger had become clearer. As a young girl I had been abandoned! And I had subconscious urges for a long term relationship with a man! Suddenly many things in my life made sense.

Is Angel my new Josh?

Before I unfolded and re-read the note that Angel had given me yesterday I picked up his ‘Honey Blush’ lipstick gift. Opening the tube I gave it a sniff which made me smile. “What a pretty fragrance” I thought. I walked to the hallway mirror and carefully applied it to my lips. It looked and tasted very nice. “I must remember to thank him.” I would use the wine as an appreciation gift. I used my hands to arrange my hair and blew a kiss to the girly face with pretty lips that was looking at me from the mirror.

Note worthy

I walked to the kitchen table and stared at Angel’s note for awhile before reaching down and picking it up. I opened the note and re-read it: “I’m sure I’ll be having a wardrobe malfunction soon and I’ll need the help that you offered. Call me.” The note was written on an “Angel’s Boudoir & Fetish Photography” note pad letterhead; his phone number and address were on the note.

There was a ‘PS’ that I had overlooked yesterday. “My name is actually Angelo. My close friends call me Angel. I hope you like the Honey Blush. I hope to see you soon.” I reflexively smiled as I read. My pulse went up a notch or two. Would Angel be my new Josh? Would he abandon me?

I took the note and stuck it on the refrigerator with a ‘Hello Kitty’ magnet for easy retrieval. The question became, ‘should I call him?’ Taking a quick glance at the wall clock I was glad it was only 9 AM. The day was young; plenty of time for adventure. And there was the pageant final I needed to prepare for. I was still having second thoughts about participating. It hardly seemed worth the effort.

I decided I’d give it some thought while I showered and got ready for the day. As I was turning on the shower I was glad I had bought a new set of tap pants and matching camisole.

When I was almost done with my shower I grabbed my razor and quickly shaved my legs and armpits; I was an expert. I was almost done when I decided to give my crotch a shave too; it had been several weeks. The act of pube shaving made me grin and feel pleasantly naughty. “You never know” I reasoned.

Stepping from the shower I towel dried my body but pat dried my legs; where did I read that? I applied a lightly scented moisturizer for good measure to my pubic area and my legs. It always felt nice to do so.

I had washed my hair and put it in curlers. I applied my Honey Blush lipstick again, put on my kimono and mules and headed toward my cell phone. I felt a need to make the call. As I sat to make the call my mouth felt dry and my pulse was more rapid than usual. I opened a bottle of water, took a swig and sat down.

Anyone home?

It took four rings before someone answered. At ring three I almost hung up out of nervousness. “Hello, Angel’s Photography” said the male voice on the other end of the call. “Is Angel there?” I asked. There was a brief silence before the response. “Yes, I’m here. Is this Ronnie?” There was a smile in his tone and a smile appeared on my face. ‘Oh my God, what do I say now?’ I thought. “Yes, it’s Ronnie.”

The voice on the other end chuckled softly and said, “We’ve already established that Sweetie. How are you?” I composed myself and said, “You were right, Honey Blush is my color. Thank you again. Er… what are you doing today? You said you may need some help. You know, with the pageant.” I hoped my voice sounded normal and that I didn’t sound desperate.

Angel responded, “I was just thinking about the pageant and how I could use help with a few things. I’m not sure what to wear. You know… the usual stuff. Would you like to come over? I will make us a nice snack if we get hungry. It would be fun.” Angel said encouragingly. With no hesitation I said, “Yes, I’m free today. When’s a good time to arrive?”

“Five minutes ago would have been nice but since its 10:00 AM now how does 1 PM sound to you?” Angel said.

“That sounds perfect. It’ll give me time to dry my hair and remove my curlers. I need to stop for pantyhose and a few things” I responded.

Angel paused a bit and said, “My, aren’t you the girly one! Be sure your stockings are 15 or 20 denier. We’re not into burlap covered legs in this house” he joked. If you’re feeling a bit trampy you might pick up a black set. I have fishnets if you want to try them.”

“Anything else?”

“Yes, bring your smile and an open mind.”

“I’ll see what I can do. I’ll see you in a couple hours.” Angel ended the call by saying, “I’m looking forward to seeing you again, Sweetie. Bye for now.” I hung up and wondered what I was getting myself into. I got up and went to prepare for whatever was going to happen. It would be pageant related, right? Will Angel complete what Josh and Dan had not?

Going to see an Angel

My pageant bag had my gear from yesterday. I just needed to augment what I already had. I tossed in a push-up bra and an extra two pair of panties; just in case. My MK cross body purse had a gold colored chain for a shoulder strap in addition to the traditional gold MK ‘badge’ on the purse flap. I packed my purse with my keys, wallet, cell phone, hair brush and lipsticks. I was NOT bringing any Spanx!

I put on my low profile B cup bra that I usually wear under my boy clothes and then pulled on my new camisole. I slithered into the matching tap pants. Both were a light peach color. There were no hose to put on since I was going to buy some later. I selected the pretty long sleeve blouse I’d worn on my date with Dan, pulled on my skinny jeans, slipped into my heels and was ready to go.

I stepped up to the bathroom vanity mirror for a last look. Opening my jewelry box I took out a pair of dainty gold ball ear studs and inserted them into my lobes. I retrieved my favorite anklet and attached the feminine gold chain around my ankle. ‘Nice touch’ I thought. It was another concession to my femme side. Before leaving the bathroom I paused to think things through. Did I have everything? Did I forget something? Yes I had. I had forgotten to use the enemas!

I was not sure how the evening would unfold but I wanted to be as desirable as possible; ‘you never know’ I thought. I took the time to use both of my scented enemas. Afterwards I was clean on the inside and my boy-pussy smelled nice; I was feeling pleasantly naughty.

I opened a drawer with cosmetics and ratted around for something special. I saw what I wanted in the rear of the drawer; a special shade of lipstick. Popping the cap off I twisted it out and gave it a sniff; very nice. It was a dark red maroon. I closed my eyes for a moment and images of Josh popped into mind as did the images of the lipstick rings he had placed on my cock so many years ago. I retracted the lipstick, put the cap back on and put it in my purse.

Before leaving my apartment I grabbed the three bottles of wine and put them in a pretty canvas carry bag. ‘Angel has to like at least one of these wines’ I figured.

As I was making my way to my car apartment manager Mrs. Johnson waived, “Ronald, I’ve heard you’re in some sort of a talent show.” I waved back but kept walking. “Calling it a talent show is being too generous. I have to go Mrs. Johnson; we’ll talk another time.” Mrs. Johnson went back to pruning her roses. She didn’t comment on my skinny jeans, blouse or high heels.

Shopping for bras and stockings takes time

I stopped at Macy’s for pantyhose but first found a cute maroon colored underwire demi-bra that was on a BOGO sale. It came with a couple of removable “enhancer” pads. I selected a same style black bra for my second item; it had a cute red heart decoration. ‘36B is for me’ is my new motto.

On my way to the stockings I walked past the cosmetic counter ‘just to look’ and came away with a free sample of Cashmere Mist perfume. It smelled dreamy nice on me. The sales lady and I chatted a bit about the importance of perfume when dating. She saw the new bras that I was carrying and remarked that they looked pretty. I thanked her and went looking for stockings.

Selecting the ‘right one’ took awhile so I selected three; all were crotchless. If nothing else crotchless would make using the toilet easier and in spontaneous love sessions; you wouldn’t need to remove them in either situation. I knew about the additional advantages. I paid for my items and finally got out of the store. The 30 minute drive to Angel’s wound up taking 60 minutes.

During the remainder of the drive I was thinking; ‘Angel is at least 3 or 4 years older than me. He looks as if he’s about 24 to 28 years old. I wonder where he learned his feminine ways. How does a man know so much about women’s things? And WHY is he interested in me?’ Actually I knew why; I was interested in him. Was Angel my new Josh? I mentally shrugged and continued driving.

My cell phone led me directly to my destination. Angel’s place was a large single story older home set back from the curb 25 feet further than his neighbors. Combined with a well established boxwood hedge that surrounded his house it created a comfortable green zone of privacy. It was an older neighborhood and all the homes were well maintained.

I turned into Angel’s driveway and pulled forward to an apparent parking area close to a front porch. I turned off the engine and sat awhile to calm myself. My nerve level was higher than normal. I dried my sweaty palms on my pants. I took a deep breath and exhaled slowly. Before opening the car door I freshened up my lipstick with the brand that Angel had given me.

I grabbed my pageant shoulder bag, the three bottles of wine and the Macy’s shopping bags with my recent purchases. With bags in my hand and over my shoulder I walked toward the front door, locking my car via my key fob out of habit.

The porch had a nice lattice patio cover. There were two lounge chairs, a matching porch swing, and two side tables. Each table had an unlit scented candle; the porch looked comfortable and inviting. Shifting my bra bag to my other hand I rang the doorbell and took a half step backwards. I was feeling a bit tense.

No turning back

In less than 30 seconds the door opened and there stood Angel. He was wearing a short red satin, waist long (and obviously feminine), dressing robe. It had a lot of humming birds on it. I noticed that Angel was also wearing pantyhose. They clearly showed below the hem of his robe. Angel’s top was a turquoise camisole and a matching lace sleep bra. The total image looked good to me.

“Nice to see you again, Precious! You made good time. Please come in. It looks as if you brought some things” Angel said. We did the obligatory Hollywood hug, cheek kiss and back rub. Angel playfully plucked my bra band. “I like your purse; it makes a statement. Your blouse is very pretty. Nice touch. Is someone feeling a little more femme today?” Angel said.

“Yes, I am; and every chance I get. That’s what I do; look femme” I replied.

I stepped into Angel’s living room and looked around. The place was tastefully decorated. The dark hardwood floors brought back middle school memories of gliding around on a similar floor wearing stockings with Josh. “It’s nice to see you. Thanks for the invite. I would have been here earlier but I stopped for stockings and a bra. And I brought the wine.” “Perfect!” Angel replied.

“Have a seat. Let me have the wine and I will pop one open before we begin,” Angel said. “I’ll pour us a glass and be right back. I’ll place your bag in my spare bedroom. Make yourself comfortable. The sofa is very comfortable.” Angel reached over and touched my ear. “Your ear studs are a nice. They look pretty but I have a set of gold hoops that would look even better. We should give them a try a bit later.” Angel went to the kitchen.

I looked around the place and decided that the sofa was the optimum place to sit. It faced a large bay window that had a good view of the pretty front yard and green privacy hedge. The window had lovely room darkening draperies. The single drape draw string was a gold braid that had cute tassels.

I placed my purse on the coffee table and took a seat at the far right of the sofa ensuring Angel had easy access to the coffee table and an end table for his wine. A stack of dark blue towels were on a lamp table as was a small wicker basket of condoms and lube; all were at the ready if needed.

Wine and Cheese, please!

Angel returned with a tray carrying two wine glasses and napkins; the bottle of Chardonnay was in his hand. There also was a selection of cheeses, crackers, celery, olives and salami on a tray. Angel had opened the bottle in the kitchen and he filled our glasses in short order. Angel sat down next to me and handed me a glass of wine.

“Here’s to the pageant and to looking pretty” Angel said. We ‘clinked’ our glasses, took a sip, and relaxed back into the sofa. I took another sip and placed the glass on the nearby coffee table. My wine glass clearly had a lipstick mark on it. Angel saw my lipstick smudge and smiled. “It appears you liked the Honey Blush, eh? I told you it’d look good on you. It even looks good on the wine glass” Angel joked.

I said, “I like your pantyhose; they make your legs look sleek and pretty. I see they are nude toe style. They look extra sexy.” I picked up my glass and took another sip of wine in a nervous reflex. “Thank you” Angel replied.

Moments of silence passed as we both stared out the front window. It was a relaxing view.

Angel moved a bit closer to me and said, “Make yourself at home, Precious. I was just getting dressed when you arrived. I need a few minutes to finish and will be back soon. There are some magazines on the table and a large coffee table book on ‘The Art of Cross-dressing’. The TV remote is on the lamp table next to the towels and there’s a stereo too. I’ll be back soon. I have an extra bedroom where I put your bag if you care to change outfits or if you decide to spend the night.” Angel turned and went to his room.

Author! Author!

Sitting alone I took another deep breath, exhaled and took another sip of my wine. I thought I felt the start of a wine buzz. Ignoring the Vanity Fair and Glamour magazines on the coffee table I picked up the very thick ‘The Art of Cross-dressing’ and began flipping through the pages. It was filled with interesting photos of pretty men wearing various styles of feminine clothes, lingerie and ‘little girl’ outfits.

Towards the back of the book there were about 12 pages of pretty men wearing lingerie or dressed as women engaging in a wide variety of sex acts; anal, oral, group, etc. It appeared the book, in addition to being a pictorial of images, was also a ‘how to’ of instructional photos. I was flipping pages and trying to relax; many of the photos made relaxing impossible; I feared I was seeping pre-cum. I wished that I had seen this book when Josh and I were playmates.

Angel returns

It didn’t seem long before Angel returned. She was wearing a form fitting LBD, a very classy brunette wig and perfect makeup. Her eyes were delicious looking; her eye lashes were long and beautiful. She wore a dainty gold ring, a necklace with a cross, dangling earrings and black high heels. Her perfume smelled ‘pretty’. Angel had a small jewelry box in her hand.

Angel sat down close to me. Opening the small box she held up gold hoop earrings that were about three inches in diameter. “These will look very nice on you, Precious! Do you mind if I replace your studs with these hoops?” Angel asked. I hesitated a moment, took another sip of the Chardonnay and said, “That would be nice.” I removed my studs and set them on the table.

Angel slid closer, brushed a few stray hairs behind my ears, and expertly inserted the hoops. I heard them click closed. Angel got both hoops inserted with little effort. “There now,” Angel said, “You certainly look more feminine,” she proclaimed. “Shake your head a bit and feel how they brush your cheeks; a constant reminder of your femininity. Here’s a mirror. Take a look Sweetie.”

Before looking into the mirror I remarked, “Having another person touch your ear lobes is pleasantly sensual.” I shook my head for effect and had to agree that the hoops felt nice.

Angel refilled our wine glasses. I reached over and put my hand on Angel’s nylon clad knee and gave it a rub. “Thank you for the earrings. They look and feel nice.” I shook my head again.

I took another sip of Chardonnay, stood up and placed the glass on the table. “I think I’d better change into my pageant outfit. I’ve been having doubts about the pageant” I stated. “It seems like a lot of effort with little in return for the opportunity to look girly in public.”

“You obviously like to look girly don’t you?” Angel said. It was a statement and not a question.

“Don’t we all? Speaking of wanting to look girly do you have a room where a girl can change her clothes?”

Changing clothes

I entered the spare bedroom where my bag was and closed the door. I was definitely feeling the wine. The room was large and well decorated with a feminine vibe. Towels, lube and condoms were neatly placed on the vanity and also on the night stand; I detected a pattern of preparedness.

Emptying the contents of my bag onto a bed I sat down at the vanity closed my eyes and relaxed for a few moments. I stood, removed my skinny jeans and anklet and removed my slinky tap pants. Standing nude in front of the vanity mirror I looked at my nude self; my appendage did not fit the image of a pretty woman.

I opened my package of crotchless sheer Sun Tan pantyhose (with control panel!); easily rolling them up my shaved legs. I remembered to put my gold anklet back on. My peach tap pants went on over my stockings; I enjoyed the way they felt as they slid up my nylon encased legs.

I added an 18 inch long black half slip over my stockings and tap pants. “Excellent!” I thought. Glancing again into the mirror I could still see the beginning of the crotch bump that Angel had mentioned. I was very glad I had bought crotchless pantyhose. Angel’s advice was correct again.

I swapped out of my bland looking bra replacing it with my new lacey maroon underwire demi bra that accented my cleavage. I left the enhancer pads in the bra. I did the bra shrug to align things. Instinctively I pulled my spare chest flesh, from under each armpit, inwards and upwards to create more cleavage. I was about to pull my cami back on but decided against it. I grabbed my version of a Little Black Dress that I’d worn at the pageant tryout yesterday and stepped into it with practiced ease. I knew I was going to need help again with the rear zipper. Damn zippers!

I sat at the vanity and reached for my mascara and lipstick. Just before touching the lipstick to my lips I noticed I had the wrong tube. This was not the time for the dark red maroon lipstick; maybe later. Reaching back into my purse I found my Honey Blush and expertly did my lips. I looked into the vanity mirror and pressed my lips together as usual. My mascara was next. I used a lash curler that was on the vanity.

I found the Macy’s perfume sample of Cashmere Mist that I had been given and put the smallest of dab behind both ears and another dab low on my throat. “Less is more” I thought. I brushed my hair into the maximum feminine mode. Angel had provided hairspray.

As I sat at the vanity prior to going back to the living room I could hear that Angel had turned on the stereo and was playing some soft music. I did my deep breathing routine twice, grabbed my purse with hair brush, both lipsticks, stood up and opened the door. I felt like I needed a little more wine.

Back to the living room

As I entered the living room I saw that the drapes had been closed. Angel was busy lighting a couple of scented candles. Hearing the clip clop of my heels Angel turned to greet her guest. “My, don’t you look pretty! You definitely changed into a more suitable bra… and also you’ve changed into a pretty young woman. Your pretty gold anklet is a nice touch. You look very passable.”

“Thank you. A compliment from a person with such an obvious appreciation and knowledge of femininity is appreciated. HOW did you become so informed?’ I asked. “Oh, we can discus that a bit later. Care for some more wine?” Angel asked.

I nodded my head and moved towards the sofa and wine. “I like the choice of your music. I used to dance to this type of music with a boyfriend many years ago; we liked to dance.” I took another sip and sat down.

“Who did you use to dance with?” Angel asked.

“His name was Josh. We danced on hard wood floor like these. Sometimes we pretended to be a girl band. His sister was the first person to put lipstick on me; she used to help us look pretty” I offered.

Angel raised an eyebrow at my admission and smiled as she gazed at me. “Well that certainly explains a lot of things, doesn’t it? Come closer so I can do up your zipper.”

“To cut down on the noise of those heels on the hardwood you may as well kick out of them for now; I left mine off” Angel said. I agreed and kicked my heels under the coffee table. I moved closer to Angel, turned my back and asked, “Please zip me up.”

‘Please zip me up’ I thought. Isn’t that how this all got started; how I wound up being here? I giggled aloud and waited for Angel.

Yes, it started with a zipper – AGAIN

As Angel was about to pull up my dress zipper up, not un-expectantly, she playfully copped a feel of my budding breasts. Yes, my nipples were hard again. After a few quick caresses of my titties with her thumb and fingers Angel zipped my dress closed. I was appreciative… and aroused. Angel said nothing for awhile.

“Ronnie, you smell so delectable. What is that fragrance?” Turning to face Angel I said, “It’s called Cashmere Mist. I was hoping you’d find it attractive.”

“Attractive? I find it deliciously sensuous.” Angel leaned forward and gave me a soft kiss on my neck. Outwardly her kiss didn’t leave a mark but inwardly her kiss left a vivid mark on my already active libido.

Anticipation

I sat quite for a moment staring into Angel’s eyes looking for a hint of what she wanted or what was to come. Inwardly I was quivering at the prospects of events that could happen. Angel moved closer and turned her back to face me. “Would you please zip me up, Precious?”

I smiled at the irony of her request. “Scoot a little closer, darling.” Angel moved closer. A Victoria’s Secret tag marked Angel’s satin bra. I playfully snapped her bra band and whispered as sultry as I could into Angel’s ear, “You know this requires a bra fit test.” Angel softly chuckled at the turn of events.

Like she had done to me I reached under her arms and cupped Angel’s titties with the palms of my hand; her fleshy warm breasts felt good to me. I was in no hurry. Having not received any resistance I lasciviously stimulated her nipples like she had done to me. Angel emitted a low moan of approval and made no move to pull away; for both of us it felt like the right thing to do.

I gave Angel one last tittie grope, leaned forward and kissed her tenderly behind her left ear. “Your bra fits fine and your breasts feel good enough to eat” I whispered. A moment later I had Angel’s dress fully zipped.

Angel turned to face me and gave me a lingering kiss. “Your ‘bra check’ felt magnificent to my titties and they enjoyed your touch. Maybe you should check my panties too; my clittie is feeling left out.” We both knew what that would lead to.

Part 2 ends. Follow Ronnie’s adventures in Part 3 - "Ronnie: Consummated (finally!")

Preview of part 3 –

More Anticipation

Angel looked into my eyes and leaned forward and kissed me on the lips. Not just a peck but a real kiss with a touch of tongue. My heart was pounding. Life at that moment seemed wonderful. Embolden by the moment I reached over and brought Angel close and returned her kiss in a more passionate way while caressing her pudenda bulge. The flavor and melding of our lipsticks was erotic. Still a virgin, my mind envisioned Angel’s between-the-legs appendage slipping deep inside my boy-pussy.

Story continues in part 3 and final installment of Ronnie’s adventures. “Ronnie: Consummated (finally!)”

(This story is 100% adult fiction with a liberal helping of literary license... a fantasy for some.)

For a 'feel good' story read my "Accidental Acceptance".