Pen Pals: Cumming to Las Vegas

A Pen Pal is a friend made and maintained primarily through writing. They are typically people who have never met in person and often live far apart, sharing stories, cultures, and updates via letters, emails, or messaging apps. Traditionally pen pals wrote handwritten letters or postcards using postal mail - sometimes jokingly referred to as snail mail.

Prolog

Donna and Rick (or Ricky like Donna chose to call him) had met months ago on an adult oriented photo sharing website. People visit these sites because they are amazed and perhaps aroused that all the beautiful women on the site are men. Site members make a conscience choice to join and view these photos because they have an attraction to pretty men or perhaps they have a latent woman lurking inside themselves aching to come out and be pretty. Rick’s reason for belonging to the group would become obvious over time.

Donna and Rick were not an instant connection. Over a period of several weeks Rick had made polite and flattering comments to Donna about several of her photos and had asked intelligent questions about cross-dressing, about Donna and about her LGBTQ/Cross Dressing adult fiction stories.

Over years of posting her photos and writing adult fiction Donna had learned to be wary and very selective as to whom she emailed and texted with. It took awhile but eventually Ricky earned Donna’s trust.

The majorities of members of groups like hers are heterosexual and consist of cross-dressers, drag queens, gender fluid, transsexuals and the curious. Some members were openly queer, some were bi-sexual and some were unsure of their sexual orientation; all freely shared photos of their femme selves and sometimes they exchanged emails and texts.

At first Donna and Rick fell into the “unsure” category but over the months and many emails and mutual encouragement they were now open to exploring option two. A meeting in Las Vegas would answer a lot of questions and remove all doubts.

Getting acquainted

Untraceable anonymity of texts and emails creates a false sense of security. Being anonymous and hundreds of miles apart creates a situation where intimate information, secrets and fantasies that would NOT be normally shared if the people were face-to-face was routinely shared via email and text.

At first their emails were innocent and bland ways to learn about each other. “What type of music do you like? Who’s your favorite sports team, band, automobile? Do you fish, ski, smoke, have pets, drink or like broccoli? You do a fine job of setting and curling your own hair! Do you always wear panties? Do you shave your legs and arm pits? Are you married? What part of LGBTQ/CD are you? Have you worn ladies clothes before? Have you ever kissed a boy? Have you wanted to kiss a boy? Were you subjected to petticoat punishment or forced to play ‘dress up’ as a child?”

The idea of meeting in person

As time passed and their trust level grew their questions, stories, thoughts, desires and ‘secrets’ became less innocuous, more direct and sexual in nature. The idea of meeting in person began.

“How frequently do you pleasure yourself? How do you pleasure yourself? Have you had a same sex experience? Have you wondered about having a same sex experience? When did you first know that you were a girl inside? When were you last intimate with your wife? Have you used sex toys or butt plugs? Have you considered it? Do you want me make you pretty? Will you please make me pretty…again?” The subject material of their emails had no boundaries.

That Donna was an accomplished writer of 42 adult oriented LGBTQ/Cross Dressing fiction stories piqued Rick’s interest and he had read many of her stories which often led to a delightful masturbation sessions; perhaps together Donna and him could create a story of their own. Donna’s background and life experiences called to him and his libido. He, like Donna, was bicurious.

Recent email examples

Ricky: “I can’t wait to meet in person, to set your pretty long hair in tightly rolled curlers and caress and kiss your lips and face Donna; that’s where I would begin, I’d then hold your body snugly against mine, devouring your beautiful feminine face with my hungry eyes and passionate lips. I’d cup and caress your womanly breasts until your perky nipples became aroused and needful for a man’s attention; I’d worship them with my lips and tongue until your passions and sexual needs became urgent. Miss Donna you are a special lady with special body parts and I want to explore and touch every inch of it and you! I want you to want me make love to (all of you) you.”

Donna: “I’m ready to please a man, to please every inch, in every way possible; I want to feel your firmness thrusting, throbbing and ejaculating your seeds deep inside my boy-pussy; I’d grip and milk you in ways you have never experienced before. I may even convert you into a girly-boy male lesbian.”

Ricky: “I like the thought of ALL of this Donna. Because I’m kinky, I am going to set your hair in tight rollers, then I want you to please me, hair in curlers with your tongue and snug red colored lips on my penis until I fill your mouth with multiple doses of my creamy sperm; I want to enjoy the sight and feel of a beautiful feminine special woman like you sucking my cock until my toes curl; I want to fill your pussy and thrust repeatedly into your boy-pussy until you orgasm and I want to become intimate with your boy-bits.”

Donna and Rick: “It would be thrilling to meet in person to get better acquainted and explore our mutual curiosities and needs; and certainly much safer that hooking up with total strangers. My boy-bits look forward to your attention. Las Vegas would be the perfect place for a rendezvous!”

Donna: “And what, my darling, do you want done to YOUR boy-pussy? I’d be happy to fill it for you darling especially if you were wearing ‘open-in-the-back’ red panties; who knows, you may like being fucked more than you than you think; maybe you’ll prefer sucking cock. Perhaps meeting in Las Vegas will restore long forgotten moments of your childhood that trouble you. I KNOW such thoughts and faded memories have crossed your bi-curious mind on several occasions in our emails. Xoxo.”

Donna and Rick: who they are they? Background information

Donna: is in her early 60s and has known she was not a boy by age 4. In high school she already had tubes of her favorite lip sticks, favorite mascara and a favorite makeup. She had been cross-dressing to some degree all her life but had really blossomed during high school and again after her military enlistment was over. She had her ears pierced by age 20 and is convinced she is trapped in a wrong gender body. She sets and curls her own shoulder length blond hair. Donna had thought deeply about transitioning in her mid 20s but decided against it.

By her late 20s, without pills or hormones, Donna had developed size 36B breasts; not ‘man boobs’ but honest to goodness womanly tits! She took this as further confirmation that she was meant to be female. Her chest is now a natural 38C and her underwire bras make her profile look stunning. On occasion, while trying hard to be in ‘boy mode’ Donna wears a neutral colored sports bra under her shirts to flatten her chest.

She continues to be closeted to friends and family but keeps ‘girly’ to her inner self by wearing her hair shoulder length, keeping her legs, armpits and other body parts clean shaven. She paints her toe nails neutral beige and wears stockings and panties under her boy clothes at every opportunity. Her collection of earrings and studs is extensive with 2 inch gold hoops being her preferred style. She is 5’ 8” tall. Donna has been married for more than 30 years but has not been intimate in over eight years.

Donna expresses her feminine side by posting photos of her in ‘girl mode’, writing adult fiction and in emails to a few special on-line friends, like Rick. Donna has been known to flirt and wonders about her possible bisexuality. What is she missing out on? Would being intimate with a man confirm and complete her femininity?

Donna wondered: ‘Am I woman enough or bi-enough to perform the ultimate acts of sexual pleasuring a man; am I woman enough to allow a man to pleasure me? to surrender and be bred and inseminated?’ These erotic thoughts were fantasies that she wrote about and dreamed would come true. A trip to Las Vegas to meet her pen pal seemed like good way to sort things out.

Rick: a middle-aged male, self-employed journey level electrician and care giver to his disabled wife. Rick is a self taught hairstylist that for many years has earned extra money by working from home as a hair stylist taking care of friends and neighbors. Rick has a fetish for long haired individuals (like Donna’s) regardless of their gender; he loves using curlers and doing tight sets on people. The smell of hairspray, setting lotion and the teasing and coiffing of hair into a feminine image of beauty is an aphrodisiac to him. Styling a males hair into a feminine beauty is one of his most erotic fantasies; envisioning a pretty boy taking care of his sexual needs after he had styled his hair would be a wet dream that came true.

Dressing as a woman and having sex with a man was also a fantasy of his. There was an event or experience from his distant past, maybe at age 8 or 9 that was whispered about among the adults when he was young that nagged at his subconscious and fueled his present curiosities. Perhaps it involved a distant relative or a long forgotten family friend.

Because of Donna’s feminine photos, long hair and adult fiction stories Rick began to wonder what it would feel like to get pretty, wear lingerie and present as female on occasion. There was something from his forgotten youth that reinforced these thoughts and desires and is why he joined the ‘pretty-boy’ site. Rick is 5’ 11” tall and keeps his almost shoulder length hair picture perfect.

Rick is inwardly bi-curious and has had the secret desire to engage in same sex love for many years; he wonders if he has the courage to follow through with such fantasies. Donna’s ‘naughty’ stories and his repressed memories fueled his latent sexual fantasies but he remains deep in the closet. Rick has been married longer than 25 years but due to his wife’s serious medical condition he is more of a caregiver than a true husband; there’s been no intimacy for many years.

It was Donna’s long and self styled blond hair that initially attracted Rick to Donna; her other more exotic feminine photos were a plus. Photos of her 38C cup breasts and cleavage were very exciting to Rick as were photos of her in lingerie, pretty dresses and makeup. He dreamed about styling her hair.

Viewing her made up face sporting pierced hoop earrings made it even more exciting when you realize that she, like him, had a penis; Donna called her unwanted appendages ‘boy-bits’. Rick’s curiosity and erections grew at such thoughts. If Donna could be pretty why couldn’t he? Maybe being with a girl like Donna wouldn’t be such a bad thing.

Their story

The two long distance pen pals, and potential lovers, had planned that their first meeting would be in Las Vegas during overlapping vacations when they’d both be there with their wives. How they could find enough free time to meet and become ‘acquainted’ was a detail still to be resolved. Another detail for Donna was how to be androgynously feminine enough to impress Ricky yet not so gay looking femme as to draw embarrassing attention from the general public.

Being more familiar with Las Vegas Donna selected the Silver Slipper Casino and Bar as their meeting place. It is a smaller less trafficked local’s casino that she frequented now and again. It also had 20 nice hotel rooms in the rear area. Located one block off the Strip near Harrah’s and the Venetian it was close enough to be able to change clothes and become pretty while her wife went shopping, caught a show or lounged by the pool. It was a short walk.

Donna and Rick agreed to meet at the ‘Second to None’ sports bar in the rear of the Silver Slipper casino on a Tuesday at 1 pm. “Be sure to wear a flower in your hair!” joked Rick. He would be in jeans, a long sleeved cowboy shirt and upscale Tecovas cowboy boots. Donna would be pretty.

First Meeting

Donna made a point of arriving early so she could find a seat facing the front of the casino. She was wearing a colorful tropical print short sleeved blouse; white cotton stretch above the ankle skinny jeans and unisex brown loafers with a gold buckle. Her taupe thigh high stockings looked nice with her shoes. She carried a Vanilla colored medium sized MK clutch purse for her ID, money, credit cards, a sparse amount of cosmetics, a few tissues and a travel sized tube of lube. The clutch purse was large enough to also accommodate her cell phone and a tortoise shell hair brush.

Donna’s makeup was sparse consisting of mascara, eye liner and a hint of blush augmented by a light coral shade of lipstick. Her short but manicured nails were clear coated, shiny and went well with her attempt to be subtle. She had opted for small pearl ear studs rather than her favored two inch gold hoops. Her shoulder length blond hair looked nice and a pretty hair clip was a perfect accessory. As a fashion statement oversized ladies sunglasses were fashionably perched atop her head. She had remembered to apply a very subtle amount of ‘Cashmere Mist’ musk perfume.

Donna found a seat at the video poker bar that was good for her. The bar could accommodate 75 people yet there was only four other patrons at this time of day; the bartender appeared to be bored.

Donna reached into her purse, retrieved a $20 bill which she fed into the video poker machine. As if by magic the bartender appeared and asked, “What are you drinking lady?” Donna ordered a Cosmopolitan and put $2 into the bartenders tip cup. She began slow playing one coin at a time and sipping her cocktail as she awaited her “date”. Her heart rate was nervously high. She sipped some more.

Rick arrives

Between poker hands and sips of her Cosmo Donna kept a nervous search of everyone entering her part of the casino. And suddenly he was there; standing tall and handsome on the opposite side of the bar!

The two made eye contact and just stared at each other a moment; subtle smiles formed on each one's face. Ricky winked and walked to meet his long distance pen pal. Donna’s initial response was ‘Hmmm, he's more handsome then I thought!’ Donna stood up from her barstool as Ricky approached.

As he walked to meet her Rick was pleased at the way Donna was dressed. Her nicely pressed white skinny jeans, colorful blouse and hair looked great. "Her hair is not as long as I had hoped but the pearl ear studs and her perky breasts sure make a statement that she is a she."

As they met they outstretched their arms and held her each at arm’s length as each one absorbed the moment. The warmth and softness of Donna’s palms was pleasant. Rick held her hands a bit longer than usual as he admired her manicured and feminine fingernails that shone with a clear lacquer. They embraced.

The feel of Donna’s breasts as they pressed against his chest as they hugged was exciting to Rick. The subtle wafting of Donna’s perfume caused Ricky’s nostrils to flare; to flare like a stallions nostrils flare when near a mare in heat.

In unison they both said ‘You look beautiful/handsome’. They giggled at the oddity of saying the same thing at the same time. Rick kissed the back of Donna’s hand. Not to be out done Donna leaned in and kissed Ricky briefly on his cheek; the two hugged.

Donna brought them back to reality by asking, “Hey handsome, care to buy a lady a drink?” Rick laughed, smiled and escorted Donna back to her bar stool and took a seat on her right. Following casino protocol Rick inserted $20 into his machine.

When the bartender came for his order Rick said, “Another Cosmo for my lady and a Maker's Mark on the rocks for me.” He placed a $5 bill in the tip cup.

As the drinks were being made their eyes continued absorbing what they were seeing for the first time. The visuals were pleasing; so much better than their sometimes bland and monochrome emails. Now their conversations were in beautiful living color!

As the drinks were delivered the two raised their glasses as if to make a toast; Ricky was sure he saw an 'air kiss' being sent his way as they sipped in celebration of finally meeting.

The two sat and began nonchalantly playing video poker while making idle conversation as they pondered what to say... what to do. "Your eyebrows and lashes look pretty" Rick said.

“Just for you I shaped my brows and used a bit of eyebrow pencil and mascara. I’m pleased you noticed. You must let me do the same to you someday.” Donna fluttered her lashes. Knowing that he had mentioned that very thing in their emails Rick pondered her suggestion.

4 Queens (and one is Donna)

After his third hand of video poker Rick chortled, "I just got three queens!" Donna took a sip of her Cosmopolitan and sexily said, "Well darling, if you count me then you have four Queens which has a much nicer payout than mere cash." Donna briefly placed her warm hand on Rick’s thigh for emphasis. She was determined to not make the first move; after all she was the lady in this story.

Ricky absorbed her comment and said, "You'll always be Queen of my heart baby-doll."

“And you’ll always be my Queen darling” Donna retorted.

Rick leaned close enjoying Donna’s intoxicating feminine scent. Not caring who was watching Ricky gently kissed Donna's cheek. Only the bartender noticed.

Ricky gently placed his left hand under the bar and on Donna’s right thigh and gave it a tender rub and left it there; he could feel the heat that was Donna. Donna did not object.

Donna reciprocated by placing the palm of her right hand on Ricky’s left thigh and, with one of her fingers, began slowly drawing tender circles on his inner thigh.

Thus encouraged Ricky smiled and moved his hand onto Donna’s inner thigh and upwards towards the ‘promised land’. The tip of his little finger touched Donna’s pudenda through her pants and he began petting where he expected her boy-bits should be. Rick made an audible gasp that made Donna smirk. “Looking for something cowboy?” she asked.

Rick stammered an awkward “Where’d it go?” a not so subtle reference to Donna’s penis. Grabbing Rick’s hand she pressed it deeper between her legs and clenched him with her thigh muscles. “I put it in a special place where all girls like me always tuck their jewels.” Donna released her grip; Ricky withdrew his hand. Donna laughed.

Time to make a move

After a long gulp of his Maker's Mark and without asking Ricky hit the ‘cash out’ buttons on both of their poker machines, retrieved their chits, drinks, Donna’s purse and they both stood up. His mouth felt dry and his palms were damp in excited anticipation of seeing and exploring Donna and her special clit hiding place. A familiar and pleasant stirring had begun in the crotch of his new Levi's.

“Bartender, we’ll take two more of the same and we’ll be sitting in the booth at the back of the bar.” The bartender winked, smiled and nodded in agreement.

Rick gently took hold of Donna's elbow and guided her to an intimate 4 person padded curved booth away from the more heavily trafficked casino floor. They slid along the padded booth and behind the table cloth covered table. An unlit candle in a decorative glass holder was an unused center piece.

Donna placed her purse beside her and demurely crossed her legs; the sound of her stockings rubbing her pants was subtle but unmistakable. Rick’s mind wandered to what style of panties, if any, that Donna was wearing.

They were holding hands and making nice when the bartender brought the fresh drinks. He placed them on coasters directly in front of them; the bar tender had added a pretty orchid garnish on Donna’s Cosmo. Rick took the orchid and placed it behind Donna’s right ear. “A flower behind a right ear means that the maiden is available and looking for love” Rick explained. Donna blushed and kissed Rick on the cheek, “Thank you darling” she said. Rick paid the bartender with cash telling him to keep the change.

Rather than leave immediately the bartender spent a few moments looking at them as if figuring out what the deal was with these two customers. Finally he grunted as if he had an epiphany of awareness and retreated back to his bar.

For the first time in her life Donna felt that she was on a date… a date with a man! A random tear of happiness trickled down her cheek.

Rick noticed a thin gold chain dangling with a hummingbird pendant around her neck. 'Dang, Donna's too feminine to have ever been mistaken for a male' he thought. "You look beautiful" Ricky ventured.

Donna smiled coyly, reached up and removed the hair clips from her hair. She used her fingers to spread her crowning glory to feed Ricky’s hair fetish.

"Care to give my hair a tease and fluff, darling? I have a travel sized hairspray and Velcro curlers in my room."

Rick replied “I have a complete set of everything in my room that I brought just for you. I'd love to get my fingers into your hair and make you prettier.”

“That all wonderful but let’s not forget that we both have more urgent carnal needs that we need to resolve!" Donna replied. Inwardly she thought, ‘The sooner, the better’.

A glance at Rick’s crotch confirmed that he was in need of relief. For years it had been Donna’s dream to be in a position where she could hold and relieve a man’s sexual tension.

Rick put his arm around Donna, pulled her close, and kissed her passionately on the lips. In return Donna reciprocated his kisses and placed her hand under the table and on Rick’s zippered bulge and began a teasingly tender stroking of his pants enclosed penis.

I kissed a boy and I liked it!

Kissing Donna, a biological male, was more pleasant than he had thought it would be. Ricky had never kissed a boy before but kissing Donna was so much different that he had imagined. She kissed with a passion that was pleasant and thrilling; she kissed like girl!

Donna had no problem with kissing her Ricky; it was a dream come true! Even before puberty Donna had dreamed about kissing a boy and having a boy kiss her. She easily settled into the submissive feminine role of the moment and in a deliberate effort to be a little slutty she tentatively began toying and probing Rick’s lips with her tongue; French kissing with a boy had always been the object of her dreams. In terms of petting and foreplay Donna knew what males like. Rick accommodated her.

Rick spread his legs and silently throbbed his approval of her touching. Donna was thrilled to feel Rick’s penis grow and twitch. The table cloth kept everything hidden from public view. The two continued their kissing and their passions grew. They were unaware of the bartenders return.
When they opened their eyes and took a break from their ardent kissing they found the bartender standing in front of their table; they had no idea how long he had been standing there watching them.

Al explains things

Al was carrying a drink tray that was loaded with about a half inch of nice paper dinner napkins, a doggie bag, 1 shot of Maker’s Mark bourbon for Rick and a shot of Ketel One vodka for Donna. He placed all the items on the table in front of them and the tip tray in front of Rick.
“What’s this all about?” asked a puzzled Donna.

“I’ve been working this bar for over 15 years and a couple like you who sit back here are usually trying to get “comfortable” with each other. I don’t want you using my table cloth as a cleanup rag after getting “comfortable” and I certainly don’t want you soiling my carpet.”

“And the doggie bag?”

“It’s to put your dirty napkins and condoms in after you’ve cleaned up your messes.”

The bartender slid the tip tray towards Rick and said, ‘$40 gets you 30 minutes and then I want you two to move on. Capiche?”

There was no immediate reply from the stunned couple.

The bartender continued: “Our casino has 20 clean and comfortable rooms. Go to registration and ask for Alice. Tell her that Al the bartender said to give you the ‘lunch time special’. You’ll have a room from 12 noon until 5 PM at a reasonable rate; take a shower if you want.”

Rick placed two $20 bills on Al’s tip tray and slid it towards him. Before the tray got within his reach Donna had retrieved a $10 bill from her purse and tossed it on top of Rick’s money.

“There’s an extra $10. We’ll be gone in 45 minutes. Women should never be rushed when doing things they enjoy.”

Al took his tray, smiled, nodded his approval and left.

Rick was impressed with Donna’s quickness of response. “You handled that very well” he said. Putting her hand back under the table she once again fondled Rick’s crotch and quipped “I handle many things very well!”

Getting down to business

Donna’s purse was still open and she retrieved a gold colored tube of lipstick that was darker, redder and more dramatic than what she was wearing. Using a compact makeup mirror and with practiced ease she redefined her lips; the new color also defined new intentions.
Rather than put her tube of darker lipstick away Donna kept it in her hand. She leaned over and kissed Rick on the lips making sure to transfer color to his lips. He didn’t object. In fact he ran his tongue over his lips to taste what he had been missing. “That color looks good on you babe, you should give it a try; it works for me.” Donna and Rick had joked about ‘feminizing’ Ricky and getting him in panties via emails on several occasions.

Table Games

With Rick’s arm around her and while holding her snuggly against him, Donna’s hand was busy under the table. She found his zipper and pulled it open; her hand found the fly of his boxer shorts and his manly hardness was in her grasp. Rick was panting in anticipation of what was about to happen. Donna let go of her warm prize and sat upright.

Although she still had more than half of her Cosmo left she grasped and downed the shot of vodka that Al had brought; she had a nice alcohol and sexual buzz going. She could always blame what she was about to do on the booze.

Turning to Rick she said, “I’m not going to do all the work here. You need to pull your woody out from its hiding hole and slowly stroke it until your pre-cum makes it slick and hard enough to warrant my attention.”

Rick did as he was ordered and was soon actively stroking himself towards an orgasm.

After a few more sips of her Cosmo Donna reached under the table and checked on the status of Rick’s prick. Yes it was very hard and yes it was very slippery. She scooped up some of Rick’s wetness using her finger and brought her hand above the table.

She showed Rick his pre-cum puddle and smiled. “You can stop jacking off sweetheart. Your boy-bits are perfectly ready for me.” Rick watched in awe as Donna licked her finger clean. The sight almost caused him to spontaneously ejaculate.

Donna retrieved a second helping of Rick’s pre-cum and brought it to Rick’s lips. “Taste what I taste, show me that you can be with a man. After all we have been discussing bi-sexuality, right?”

Hesitating but a moment Ricky complied with Donna’s request; the suggestions and requests that she had made in the emails over the months were becoming reality. Rick performed a type of finger fellatio on Donna’s wet finger. The taste of his pre-cum was not unpleasant and had a vague reference to something he had tasted before. ‘I have to do this again at my next opportunity’ he thought.

Donna picked up her gold tube of lipstick, retrieved the lube from her purse, drank half of Rick’s bourbon ‘liquid courage’ and ducked her head under the table and put her face in front of Rick’s protruding wet cock. The alcohol and her lust had fueled her libido and she was determined to become a cock sucker!

Donna’s First Blow Job; a mouthful of pleasure

Recalling the many porn BJ instruction videos she had watched and the adult stories she had written Donna had a solid understanding of how to orally please a man. She was eagerly looking forward to the ‘warm wet reward’ that would be filling her mouth if she did things right. Her arousal level was mounting.

She grasped Rick’s shaft at the base and tilted it towards her mouth. Rick obliged by slightly rotating his pelvis to give Donna the best cock sucking angle. Before ducking under the table Donna reapplied her lip color.

Prior to beginning her lurid quest for cum she made sure to kiss Rick’s cock multiple times in multiple places; she was proud of the lip prints she was leaving. It was just like what she wrote about in her stories.

She held his penis and coated her lips with his pre-cum as it seeped from his pee slit as if his penis was a large tube of lip gloss. Donna was becoming aroused like she had never been before.

Donna spread Rick’s copious amounts of his pre-cum all around his bulbous cockhead with her thumb before gripping behind his corona and glans with her lips making sure to leave colorful lip prints where ever her lips gripped his penis; she was ‘marking’ her territory!
Donna began licking and swirling her tongue on Ricky’s spongy glans before letting the snug ring of her colored lips slide down Rick’s rigid shaft; the feel of his penile veins fueled her lust.

Rick’s involuntary throbbing and copious seepage of pre-cum encouraged and excited her. Donna was certain that her panty liner was hard at work in containing her own seepage. The moment was just as she had dreamed about.

When Rick’s cockhead hit the back of her throat she froze in place and then, while maintaining suction, began a slow upward glide to where she had started. She used her talented fluttering tongue to tease and tickle and her snug lips to milk him as she moved up Rick’s penis. Upon reaching the tip of his prick she let her tongue dance and swirl in and around the ridges of his corona, veined shaft and at the entrance to his ‘pee-hole’ (meatus). The throbbing of Rick’s penis was exciting and becoming more frequent.

Rick’s low moans and pelvic thrusting were Donna’s reward for a job well done… a blow job well done!

"New" source for pleasure?

Sensing Rick’s orgasm was nearing Donna removed the cap from the lube and liberally greased her index and middle fingers.

As she resumed her sucking and in an inspired move she used her free hand and one of her lubed fingers to probe Rick’s virgin boy-pussy. With sexually charged determination Donna found her target. When she first made contact with Rick’s puckered pussy she liberally spread the lube in circles around his anal ring before sliding a glistening finger partially inside his orifice. Donna was taking her time.

Rick gasped in pleasant surprise and made every effort to attain maximum digital penetration by trying to wiggle his butt deeper onto Donna’s determined finger.

Donna obliged Rick’s latent desire and gave Rick full rectal finger penetration and began the finger fucking that he so obviously wanted. As Donna continued her anal ministrations on Rick’s pussy she said, “Think of all the sexual pleasure that you’ve been denying yourself for years my sweet Sissy boy. Would you like me to stop?”

Rick obviously enjoyed having his pussy diddled. It was something that he had fantasized about for a long time. Rick loved the sensation of being sexually penetrated; he expertly gripped and milked Donna’s fingers like an experienced pro with his anal muscles. ‘My Sissy bitch is in heat so let’s see how he reacts to having something larger poking his pussy’ she thought.

Donna boldly inserted a second finger into Rick’s once virgin hole and began probing and twisting her fingers for Rick’s delight. Thinking ahead Donna spread her fingers in order to loosen up Rick’s virgin canal for future penile penetration. Although his pussy was not as tight as she thought a virgin’s love hole should be she did feel a band of sphincter muscle release and relax as she continued to finger fuck Rick. He should now be able to take the girth of her boy-bits with no pain.

Rick’s strong reflexive gripping of her finger bode well for when she’d eventually fuck him with her penis. When she wiggled and slid her finger deeper into Rick’s receptive boy-pussy he mewed like a kitten and emitted and audible grunt of delight; “Oh, oh, oh my god…wiggle your fingers!” he implored. Ricky gyrated his butt like a bitch in heat in an effort to maximize his pleasure.

Donna grinned “It appears my Sissy boy likes having his pussy fucked! I want you to dream of what the real thing will feel like when I have my way with you! I’d rub your prostate now but your screams of pleasure would bring Al quickly back to our table.” Donna resumed her cock sucking as she continued reaming him; Ricky quivered on the edge of Orgasm Canyon.

Unexpectedly from deep within his subconscious a memory from his youth surfaced and with his eyes clenched tightly Ricky begged “Oh my god! Please don’t stop, it always feels so damn nice! I promise I won’t tell anyone!” Donna ignored Ricky’s involuntary admission of having been previously penetrated.

‘Perhaps his sexual fantasies are subconscious desires based on real life experiences’ she thought. ‘He’ll love it when I make him my bottom and peg him through open back panties!’

Ricky’s lower body stiffened, his pelvis involuntarily thrust multiple times and he orgasmed like never before. He was unaware of what he had verbally divulged during his moment of rectal passion.

Analgasm!

His ejaculations were more powerful and prolonged than ever before. He came 4 or 5 times deep into Donna’s receptive mouth and throat. Rick had just had his first analgasm! His pussy tried to keep Donna’s fingers from leaving and he enjoyed having her fingers dragging against his pussy membrane as she withdrew her fingers from inside of him!

He vowed to have more of what Donna was giving him; he hoped it would involve more than just fingers. ‘There’s no doubt that I’m bi-sexual’ he thought. He loved the fantastic mini-orgasms that followed!

Rick was fully satiated and content; it had been a wonderful day. The only problem was that he was still, technically, a virgin. Or was he? Had that ship already sailed many years ago in his past?

Clean up on aisle 69

Grudgingly accepting the fact that she had sucked Rick dry Donna slowly withdrew her fingers out of Ricky’s boy-pussy making sure to rub his rectal nerve endings.

She peeled her mouth and lips from Rick’s deflating appendage, released him from her grasp and poked her head above the table; the coast was clear! Bartender Al was chatting up two pretty ladies at his almost empty bar and was facing away from them.

Donna had a content smile on her face and a puddle of warm sperm on her chin and cheek. She used one of bartender Al’s napkins to dab her chin, cheeks and blouse and another to clean her fingers of Rick’s seeping pussy juices. She placed the soiled tissues in the doggie bag like Al suggested.

Donna allowed Rick a moment to enjoy his post orgasm afterglow while she applied fresh lip color.

Rick looked lovingly at Donna and softly said, “That was fantastic, thank you. How will I ever be able to reciprocate the experience that you have just given me?” “Oh, I’m sure I can come up with an idea or two” Donna replied.

Feeling very decadent Rick leaned over, kissed Donna tenderly on her sperm covered lips and began French kissing her in an effort to sample and taste what Donna had just tasted. He was successful. Rick felt naughty yet sexually liberated. Rick didn’t notice or care about the additional transfer of Donna’s lip color to his lips.

Rick spoke: “That didn’t taste bad and was damn erotic; it was a like a pleasant flavor from a long time ago!” He began thinking about how soon he could fellate Donna and have her fuck him again. Being penetrated and giving a blowjob was an exciting thought that had been lingering in his sub-conscience for years.

Donna gives a review: “Darling, sucking a cock was everything I had hoped it would be. Not too much mouth stretching but just right. The texture was firm yet soft and wonderful. Your ejaculation was so fantastic and exciting, sort of like a warm creamy custard. The flavor was nice just like mine. It was a perfect experience that I can check off my ‘Suck It’ list! I’m officially a cock sucker!”

Donna laid her head back, closed her eyes and relaxed. She also slowly licked her lips with naughty visions of Ricky kneeling between her legs doing what he was destined to do. She was positive that Rick would have no problem with cock sucking; the technique would all come back to him.

Ricky said: “No darling, you are a fellatrix and a finger fucker extraordinaire! Next time you suck me or fuck me I’ll give you money and then you’ll be my whore!”

While Rick likewise cleaned himself and his wayward spurts of sperm Donna calmly refreshed her lipstick again and put it and the lube back into her purse. Her poise and sexual skills impressed Rick. His crumpled and soggy sperm soaked tissues joined Donna’s in the doggie bag.

It was getting late

Rick straightened his boxer’s, buckled his pants and sat upright; his arm around Donna. He glanced at his watch and then looked in Al’s direction. The doggie bag was bulging and Al’s time clock was ticking.

"Ricky, I only have 60 more minutes for us today but I can break away for 4 or 5 hours tomorrow and maybe for a few hours tonight after my wife falls asleep; I’ll tell her I’m going out to gamble. Make a plan and I'm yours. We need to spend time discovering each other.”

Rick agreed. He downed the last of his Maker’s Mark bourbon and told Donna to wait for him. “I’ll be back soon.” Rick headed to hotel registration, transacted business and quickly returned. “I paid extra and we have a room for tomorrow between 11 AM and 7 PM. Al must have called ahead because Alice was expecting me.”

Rick handed Donna an electronic room key and said, “The key becomes active after 11 AM tomorrow in case you want to get to the room before me. If anyone asks tell them that you are Rick Johnson’s fiancé.”

Donna thought for a moment as they sat in the booth and said “Tomorrow I’m bringing a larger beach bag tote to the room; I have pretty matching garter belts, matching bra and panty sets and extra sheer stockings I want us to wear. But first you must shave your legs. I want to see you all dolled up, looking pretty in a garter belt and stockings, on your knees, with your colored lips wrapped around MY clit! I have all the cosmetics and nail polish we’ll need. It’s time you experience the fantasies you spoke of in your emails.”

“Maybe I’ll take YOUR cherry, make you my whore and send you on your way in panties and stockings, forever hooked on lingerie and beginning life again as a sexy male lesbian!”

Rick retorted with, “I brought a beauty shop hair styling kit complete with rollers, tin foil and setting lotion. I could add some feminine highlights to accent you feminine beauty; maybe dye your lashes. I’d love to do your hair, twist the curlers so tight that you and have you on YOUR knees sucking me off while I’m in a garter belt and stockings! Just the thought is making my dick so damn hard.”

Donna shrugged and smiled before saying, “Well Sweetie, I guess we are bi-sexual.”

The two stood up. Donna leaned over slightly, dangled her breasts and shrugged to reposition her titties back into their soft nesting place inside her white satin demi-bra; this reflexive feminine move caught Ricky’s attention. “You still owe me a peak and tour of your perky breasts Sweetheart” Ricky reminded.

“No problem darling. There’s always tomorrow. I’ll even let you ‘tittie fuck’ them IF you make yourself pretty and wear your garter belt and stockings. I’ll keep my mouth open and we’ll see how good your aim is. Another taste of your ‘love custard’ would suit me fine.”

“It’s a deal!” Rick exclaimed. All of what Donna had just mentioned, him in panties and tittie fucking her while in a garter belt and makeup, created yet another strong stirring in his pants. Rick had dreamed and wondered for many years about cross-dressing, “looking pretty” and being intimate with a man would be like. After all no one forgets how to ride a bike.

Before tomorrow was over he would know what destiny and his past had in store for him… or her.

They stacked their cocktail glasses, unused napkins and bulging doggie bag neatly in the center of the table and left. The table cloth was clean and pristine.

They hugged and kissed goodbye and held hands as they left the Silver Slipper. Donna was determined to take her public femininity to a new level tomorrow regardless what others thought. ‘What happens in Vegas Stays in Vegas’ was her new mantra. She regretted not bringing a cute dress and her kitten heeled high heels on her trip but she knew that tomorrow all her nails would be a bright sexy red. And so would Ricky’s. She made a note to not forget the nail polish and makeup remover.

Donna smiled as they were leaving, ‘With any luck by this time tomorrow I won’t be a virgin and neither will Ricky since bi-sexuality is a two way street. Maybe I’ll pay him $2 dollars after he blows me and make him MY whore!’ Donna grinned at the irony of it. She also wondered how long it would take for Ricky to realize he was wearing her lipstick.

“I know that all the pretties I brought for you are your size”

“Ricky you may arrive in boxer shorts but you’ll leave wearing sexy panties, stockings, a bra and having painted toe nails just like you’ve dreamed of and which your faded memory can’t or won’t let you recall.”

“To know your future you must know your past” - George Santayana