“Sissy Nickie: Begging to Be Pegged”

Synopsis: This is a lovely "cumming of age" story as young Nickie evolves from being a child to adulthood. Nickie and his family struggle with thoughts that he may be a Sissy; perhaps he isn’t.

The story unfolds

Nickie was an attractive and very passable cross-dresser, in his early 20s that lived near London. In reality he had surpassed being a mere cross-dresser by the age of 13. Despite being femininely pretty Nickie was a shy virgin that desperately wanted to experience same-sex love.
He was so anxious to lose his virginity that he bought and paid for an insemination and breeding session from a pretty local pub Queen named Miss Donna; losing his virginity was an important life goal of becoming as feminine as possible without surgery.

The thought of having eight inches of beautiful Miss Donna plunging repeatedly into his virgin boy-pussy and having copious amounts of her delicious sperm injected deep inside of him made Nickie very aroused; it would be a Sissy dream comes true.

At his request Miss Donna promised to “cork” his boy-pussy with a tampon immediately afterwards in order to keep her slippery ‘syrup’ from escaping and dribbling down his leg; Sissy Nickie wanted his body to absorb as much of Donna’s essence and DNA as possible in the hope that it would enhance his own femininity.

Nicholas was looking forward to having the tell-tale string of a tampon dangling from his Sissy love hole; the tampon would be the ultimate symbol of having been consummated and proof of his femininity.

Nickie knew everything about giving and receiving oral sex since age 12 but was ignorant about same sex intercourse is like; she hoped it would confirm the femininity that was him.

How it all began

Nickie’s mom had divorced his father before Nickie had turned one year of age; there was never a father figure in his life. His family consisted of a sister, Nancy, three years older than him and his divorced mother. Being a single parent meant his mom worked long hours to make ends meet and was forced to hire a babysitter to watch after her kids.

Long hair

Low income meant that Nicolas inherited his sister’s hand-me-downs clothes which would not be a big deal until he entered kindergarten. His mother saved money by foregoing the expense of haircuts and letting his hair grow out, uncut, like she had done with his sister.

Nicholas and Nancy wore matching hairstyles with matching barrettes to reinforce that they were sisters. Mom and the babysitters told people they were sisters and always dressed Nickie appropriately; they also brushed and fixed his hair just like they did with Nancy.

The baby sitters and mom relished in making Nickie look as little girl feminine as possible; he was their living play doll and they loved to see their girls with twin ponytails. Nancy and Nickie were undeniably cute sisters.

Long hair that began out of necessity became the usual; what had been the usual became the personal preference for Nickie throughout his life; ponytails and hair clips were a favorite.

By age five Nickie had more hair barrettes and panties than his sister. Princess liked a variety of panties but as he grew older he, and his boyfriends, loved the ease and practicality of rear access panties.

At a young age Nicholas knew he was different than other boys. He was shorter and weighed less than his male peers and his delicate features did not scream “boy”. His innate demure personality and Nancy’s hand-me-downs allowed him to blend in and be accepted by his female playmates as an equal; Nancy’s playmates were his playmates too.

During his primary childhood (age 5 - 8) Nickie took every opportunity to be one of the girls by playing My Little Pony, Little Mermaid, jump rope and of course engaging in ‘dress up’; Nancy helped and encouraged Nickie to be a girly good sister at any chance she had; Nancy gave him the nickname of Princess when he was 5; it wasn’t very long until Nicholas’s mother, his babysitters and neighbors also began addressing Nicholas as Princess.

It was during this time, around age 8, that Nicholas began having erections.

Over time, by being constantly immersed in femininity, Princess absorbed girl like mannerisms, speech patterns, interests and desires. Nancy knew that Princess wanted to be like her; to wear dresses, paint his nails and lips like the other girls did; Princess wanted to look pretty and not just on Halloween.

First Wet Dream!

At age 11, in an effort to feel more like a girl and pretty, Nickie, with the aid of his sister began experimenting more openly at home with his mother’s lipstick and his sister panties, dresses and shoes. It was also the age while sleeping and dreaming in bed that he experienced his first wet dream and ejaculation; the lovely sensation woke him up! It was a marvelous feeling and he wanted more of it.

Taking the situation in hand

Princess reached into his now wet Hello Kitty cotton panties to explore the source of the wetness. He knew that the toe-curling ‘tickling’ feeling had emanated from his stiff little penis and when he grabbed himself he discovered that his still rigid penis was coated with a very slippery substance; his little cock magically twitched pleasantly at his touch

Encouraged by the throb of his penis he let his hand encircle his hardness and begin tickling himself by running his hand up and down his slippery shaft; the odd wetness that had soiled his panties made an excellent lubricant; the more he stroked himself the better he felt; there was very nice feeling building up deep inside of his crotch and penis; he was doing something right and there was no reason to stop.

The sensations were so pleasant that Princess began pleasuring himself more quickly; his efforts were soon rewarded with a second “cumming” of wet pleasure. His release was so strong that the squirt of wetness hit his chin, cheek and gapping mouth; it also wet his camisole and bed sheet. The warmth and viscosity of his ejaculation surprised him; the taste was not unpleasant so he licked and sucked the fingers of his right hand clean. He vowed to do this again.

Princess lay in bed and enjoyed the afterglow of his orgasm. When he had finally recovered he used tissues to clean his self and the bed sheets, making a mental note to aim better the next time. He changed his PJs, threw a bath towel on the wet spot on the mattress and fell blissfully asleep.

In the morning Princess confessed to his big sister the wonders of masturbation and together they changed the sheets and pillow case. With a knowing smile on her face Nancy quipped, “I’m well aware about the joys of masturbation Princess.”

Life goes on

Dressing up was a discreet activity that he indulged in throughout high school. His mother didn’t seem to mind seeing Princess en femme at home; she thought it was cute. Nickie began wearing girl pajama sets and camisoles to bed or when lounging on the sofa watching TV and mascara when going out; he began shaping and polishing his nails on a regular basis; colored polish at home and clear polish when leaving the house; needing to feel feminine and look pretty would be his way of life forever. He occasionally wondered if he was a Sissy.

Nickie was never destined to be a large boy and by age 12 Nickie’s adolescent growth spurt had stopped. He and his sister Nancy were the same height and weight and that dynamic would remain true for ever. It worked in Nickie’s favor because he would frequently “borrow” his big sisters clothes.

Sometimes Nancy would get upset when she came home to see Princess wearing her dresses, stockings, training bra, mascara, lipstick and heels.

“Mom!” she’d yell, “Nickie is wearing my clothes and makeup again!” She would then yell at her little sister, “Buy your own darn bras and pantyhose! And for God’s sake, if you’re going to wear my bra make sure to stuff it with socks so you look like you have titties.” Big sister had just taught her little sister something new.

Inwardly Nancy thought Nickie looked very grown up and sexy wearing her 2 inch heels pumps, short skirt, makeup and a perky high pony tail; he had pretty lips and nice legs; he even walked like a girl.

Out of respect and gratitude Nickie always took great care of his sister’s clothes; always put them back neatly folded or hung nicely in her closet. He began buying his own mascara.

A Princess finds a Prince

One summer, at age 13 or 14, Nicholas met John, a neighborhood boy that had similar desires as he did; Princess was no longer alone! It was a great relief to discover that there were others in the world like him. “Hello, my name is Nickie but my family calls me Princess.” They were a perfect match for each other.

The two played dress up, experimented with lipstick and colored each other’s nails when John’s parents were at work or when it was safe to do so. As time went by, they began talking about erections, wet dreams, masturbation and sex in general. The internet was very informative and very erotic.

The traditional male-female sex sites satisfied their initial curiosity about sex for awhile. When they found sites of boys and men that, like them, loved to look and dress pretty they were overjoyed! They were amazed to read about and see how pretty boys made love; explicit boy-on-boy videos and photos exposed them to sex acts that they eagerly masturbated to. They agreed that masturbating each other and occasionally fingering the exterior of each other’s boy-pussy was more thrilling than just pleasuring themselves solo.

The duo focused on boy-on-boy sex sites and eventually discovered the world of Sissies, Brolitas, Drag Queens and queers! During that summer they boys learned everything to know about giving and receiving blowjobs. They became fixated on all aspects of oral sex and began experimenting on each other while dressed up and wearing lipstick.

Ejaculating into each other’s hand or mouth didn’t disgust them at all; they found it thrilling and they developed a sincere fondness for ‘love sauce’. Seeing who could leave the lowest ‘love rings’ on each other’s penis became a game; they unwittingly became experts at deep throating a cock. “Are we Sissies or just Queers?” they wondered amongst themselves.

Sissy Nickie and Sissy John

Nicholas was surprised yet very pleased when John first penetrated his rectum and finger fucked him while they kissed and sucked; the sensation made him want more than a finger. Nickie began returning the favor. The two made a point of diddling and sucking one another at every opportunity. They used a lot of lipstick over the summer and decided that ‘Cherries in the Snow’ by Revlon left the prettiest love rings.

After one particularly pleasant round of sex the two lay entwined in each other arms and agreed that they were, in thought, deed and mindset, true Sissies. Being a cocksucker was not all bad.

One summer afternoon Nancy was walking past Princess’s room when she heard muffled sounds emanating from her little sister’s room; the door was slightly ajar. She gently opened the door a wider and was stunned by what she saw.

Princess and John were sensuously kissing on Nickie’s bed while fondling each other’s erections. John was only wearing a pair of socks and Princess was only in his panties. She watched, transfixed, at what she was witnessing.

When Nickie paused their passionate activities John scooted to the end of the bed, dangled his legs over the edge, spread his legs and waited. Princess retrieved a tube of lipstick from his night stand, removed the cap and skillfully coated his lips with bright red lipstick without the need of a mirror. Nancy stood mesmerized as Princess dropped to her knees between John’s wide spread legs.

Nancy correctly anticipated what came next. She watched Nickie tenderly take hold of John’s stiff penis and gently stroke it before pulling it towards his mouth; he lovingly kissed and teased John’s hardness with his lips and tongue several times before sliding its length into his mouth. It was no surprise when Princess began eagerly nursing on it.

The vision of what she was watching combined with John’s moaning and Princess’s methodical sucking was so erotic that Nancy’s legs felt weak and her body trembled; her pussy become wet.

She continued watching as Princess’s bobbing head, puckered cheeks and red lips sucked his boyfriend to orgasm. She was amazed when Nickie continued to suck while he swallowed John’s ejaculation. When Nickie had had his fill of John’s ‘love sauce’ he giggled, stood up and joined John on the bed; they immediately began kissing; the lovers were happily sharing and savoring John’s warm sperm.

Red rings of Nickie’s lipstick on John’s cock and the smile of contentment on John’s face served as proof of his sexual skills.
Nancy went quietly to her room and relieved the tension of her sexual arousal as she had done many times before; for a brief moment she was jealous of her little sister.

Sisterly advice

Later that afternoon while John and Princess were in the kitchen nonchalantly eating cookies and milk she announced, “In the future you young ladies should make sure your bedroom door is completely closed when you and Joanie are playing house; you definitely do not want mom to walk-in on what I saw today.”

The two boys were startled that they had been outed; they sat speechless as they stared at each other.

As Nancy exited the kitchen she said; “I sure hope you both brushed your teeth when your date was over”.

It was obvious that Princess was a queen and would always be a queen. Nancy knew it, Joanie knew it and so did Princess; so far mom only suspected it. How could she and mom prepare Princess and make his future easier? Nancy decided that she needed to have a heart-to-heart discussion with her mother. Something had to be done for their precious Princess, but what?

More feminine in act and deed

Before the summer ended Princess had his ears pierced; basic studs were soon replaced by gold hoops. Nickie always kept his legs, underarms and pubes femininely smooth. On a daily basis, Nickie wore his feminine finery and panties hidden under his boy clothes to school or work; socks hid his painted toe nails, camisoles served as undershirts and helped hide the training bras he often wore; long pants kept his smoothly shaved legs and stockings out of sight.

The family decides

Nicholas knew that he was different; he knew boys were not to dress, feel or act like girls; that having the feminine desires and interests that he had had for all his life was not acceptable by society so, he thought, ‘I MUST be a Sissy.’ To avoid ‘trouble’ Nickie could “butch it up” when needed but he needed more help; professional help.

After an emotional family meeting the three girls decided to make an appointment with a certified specialist in gender dysphoria.

The doctor and puberty blockers

The three girls (Mom, Nancy and Princess), in consultation with a licensed gender dysphoria psychologist,** decided that, in conjunction with regular counseling sessions, that a low dose regimen of puberty blockers would minimize and soften the blows that society dishes out to those that are different; boys like Princess.

While sitting in the doctor’s office with his family Princess asked, “What will the blockers do?”

The doctor smiled, looked at all of his three clients and began the explanation like he had done many times before for girls and boys that suffered with gender dysphoria like Nicholas.

“Here are the key aspects of blockers; they put puberty "on hold" by blocking the body's production of sex hormones. In your case they stop testosterone production which reduces genitalia (penile and testes) growth. Blockers minimize the Adam’s apple, soften your voice by preventing vocal cord development so you’ll sound more feminine and they impede facial hair growth.”

The doctor paused for questions and when there weren’t any he continued with his explanation.

“Blockers can be temporary and give individuals and their family’s time to explore gender identity without the stress of undergoing permanent physical changes like surgery. And no, puberty blockers do not promote breast growth! Breast growth, if desired, is an entirely different subject for a later session.”

The doctor handed out a treatment summary information sheet. It read in part:

Feminizing hormone therapy can:
• Improve psychological and social well-being.
• Ease psychological and emotional distress related to gender.
• Improve satisfaction with sex.
• Improve quality of life.

“How are blockers administered? Puberty blockers are given either by injection (typically every three months), or by a small implant under the skin of the inner arm depending on the patients need.

Finally, I cannot over emphasize the importance for having a strong support group and an accepting family.”
When they left the doctor’s office a few minutes later Princess had a small circular Band-Aid under the butt of her panties where the doctor had administered her first intramuscular injection. Nickie was happier than she had ever been before. So were Nancy and Mom.

**A "licensed gender dysphoria psychologist" is a licensed mental health professional who has specialized training and experience in helping clients with gender identity and gender dysphoria.

Nancy moves on

When Nancy turned 16 she discovered boys and the dynamics between her and Princess changed. She fought the temptation to ask her little sister for tips on how best to orally please her boyfriends; after all Princess seemed to be a very accomplished fellatrice. None the less Big Sister always remained supportive of her little sister; birthdays and Christmas always meant panties, makeup of something girly for her little sister.

Nickie moves on

After high school Nickie remained at home, took a clerical office job and enrolled in a one year secretarial vocational college. She continued her puberty blockers and her savings and income allowed her to begin medically supervised low dose gender-affirming hormone therapy of estrogen.

Her nascent breast buds were developing nicely and her areolas were beginning to enlarge. Her sensitive nipples became engorged and tingled when she swirled her finger on them; the swirling of her nipples also created a gentle stirring in her loins. By the time she graduated secretarial school Nickie could easily fill a B cup.

After graduating as an Administrative Assistant she took a position in an insurance office where her well groomed nails, womanly breasts and hair were not frowned upon; in fact some co-workers appreciated the image that was Nickie; she was grateful that she did not have to hide her womanly attributes from co-workers.

Nickie moved into a small but economical bachelor(ette) flat and began to dress more androgynous at work. She never wore a dress to work but selected fashionable Ann Taylor high rise straight legged pants with side zippers to ensure a smooth front.

Boring men’s shirts were discarded in favor of more stylish and colorful ladies blouses. The darts in her blouses accommodated her growing breasts nicely. She completed her business ensemble with a variety of tailored blazers; she projected a very professional image. Princess’s gender-fluidity garnered her more attention and dates.

Her biggest fashion concern was shoes: how “outrageous” could her office cope with? When she was first hired she wore very conservative and gender neutral Penny Loafer flats. As her confidence and breasts grew and as she acclimated to her co-workers and the office dynamics one day she daringly began wearing one inch heeled pumps. No one complained and she never stumbled; she had been wearing much taller heels for years.

Her social life and confidence began to expand and she began visiting clubs and pubs where there were patrons like her; places where she could be Princess; places where she would feel welcome.

Over time Nickie had accumulated a modest wardrobe of ladies clothing, lingerie, and shoes gifted to her by Sister Nancy and items that she had purchased for herself. Despite being very passable Princess was still too shy to venture regularly into public dressed en femme; Nickie limited her girly outings to parties, clubs, and ‘dates’ with boyfriends.

Nickie had talent

Throughout high school and university Nickie’s oral skills and the ability to become ‘pretty’ were appreciated by many. On occasion those special skills were a source of income; yet she remained a virgin and as a result had become sexually frustrated. Perhaps that oversight (being a virgin) was due to Nickie’s fear that man-on-man sex would be painful; or perhaps it was due to her submissive personality.

Sissy Nickie becomes infatuated

Nickie couldn’t remember where she first laid eyes on Miss Donna; it may have been at Nellie’s Cabaret or The Admiral Duncan pub that caters to ‘special’ people like her. Despite her true gender Donna was a stunningly beautiful woman that carried herself like royalty; her makeup, clothes, hair and demeanor were perfect; so was her penis. Nickie was in awe of it all.

Nickie would never forget the first time that she had orally pleasured Donna to ejaculation; it was in a secluded VIP booth at the rear of the Kings Arms on Oxford Street in Westminster. Donna had placed her hand lightly atop Nickie’s bobbing head and guided Nickie to the areas that felt best. After fellating Donna to orgasm and swallowing her seed Princess softly said, “You can call me Princess if you like.” Donna smiled, took notice and then took Princess onto the dance floor for a few dances. At that moment Nickie was high on life!

Everything about that first experience was forever etched in Nickie’s brain; she dreamed about gobbling Donna’s cock and savoring her viscous essence again. She often wondered what surrendering her boy-pussy to Donna would be like, to have Donna’s sperm swimming deep inside of her.

Nickie was an unconsummated Sissy bottom and felt incomplete. Nickie knew that in addition to several other qualities a Sissy had to be willing to frequently take a hard cock into their pussy. Like a child going to a dentist Sissy Nickie was very apprehensive about losing her virginity. She hoped that if Miss Donna agreed to fuck her that she would be gentle and break her in the right way.

Since that first time in the VIP booth every time Nickie saw Donna at a club the two would have at least one dance. And, when Donna would allow it, Nickie would suck her to orgasm. After each fellatio session Nickie would always ask Miss Donna to please take her virginity and breed her in a proper and considerate way.

Rules conditions and a stud fee

Growing tired of Nickie’s repeated begging Donna finally agreed to ‘turn her out’ but only if Nickie complied with specific conditions.
Donna’s rules were simple: be sure clean herself with an enema-douche, dress as a woman, arrive on time and pay the stud fee. Their date was set for Saturday.

Nickie would have to travel to Donna’s rural home via taxi dressed as a woman; her Sissy feminine status was to be on full display to everyone that would see her; her willingness to be in public en femme would be proof to Donna of Nickie’s commitment to becoming a consummated Sissy worthy of having Miss Donna’s cock throbbing deep inside her ass.

Princess prepares

For her travel clothing Nickie relied on what was in her closet. She selected: a print design puff sleeve mini-dress, red satin rear entry panties, matching red garter belt, black thigh high seamed stockings, black three inch heel pumps, gold anklet, an indigo-blue push-up bra, a stylish black leather MK with purse filled with cosmetics, spare panties, lube, two tampons and her ID.

Nickie added several bangle bracelets, a delicate gold heart necklace, two girly accents rings and a distinctly feminine perfume because she loved looking and smelling pretty. 2 inch gold hoop earrings, three coats of mascara, a dusting of eye shadow and blush, red lipstick with matching nail polish on fingers and toes completed her lovely image.

Nickie wore her shoulder length blond hair in a face framing shag with side swept bangs; a moderate amount of Aqua Net hairspray kept it in place. Her arched eye brows were perfectly feminine.

If Nickie failed to comply or was late Donna would turn her away to fend for herself. Taxi’s and trams are not common in Donna’s part of town; it would be a very long walk in heels to get to public transportation.

If Nickie complied, and IF her “date” with Donna went well, Donna would have her town car return her to within six blocks of her apartment afterwards; she’d have to walk the rest of her way home in public en femme.

Taxi

Except for the cab driver mentioning that Nickie smelled “very pretty for a bloke” the taxi ride to Donna’s was quite and uneventful. Nickie’s mind raced with thoughts of what the day would bring. The pending loss of her virginity was both worrisome and exciting.

Sissy Nickie arrives

When Nickie was paying her fare the cab driver quipped; “Don’t get a run in your stockings or break a heel Molly” and then quickly drove away.
Nickie took a deep breath to calm herself and tried to deny the boy-bump that was uncontrollably forming in her panties; mercifully her erection began to deflate.

Nickie walked down a short sidewalk and up a few stairs onto Donna’s porch. She nervously rang Donna’s doorbell and waited; her body was quivering in trepidation of what the day held in store for her and in excited anticipation of what she hoped would happen. A first fuck should never be hurried.

Donna opened the door and with a smile on her face said, “You’re right on time Nickie; Sissies should always be punctual. Please come in.”
Donna was dressed in a diaphanous black, loose flowing laced trimmed dressing gown that oozed with femininity. The front was open and erotically displayed a matching black bustier garter and panty set with red trim that accented her well proportioned hips; the black patent four inch stilettos looked stunning on her; she had the look and aura about her like sultry dominatrix.

After allowing Sissy to kiss her in a brief, non-passionate way Donna led Nickie to a well appointed breakfast nook where a kettle of hot water, tea and scones waited. The area had four chairs and a small table that had been preset with cups, saucers, a serving tray with scones and finger sandwiches, and a vase of pretty flowers. It was a comfortable place where they could talk and relax.

Before she could take a seat Donna startled Nickie by sternly ordering her; “Leave your heels on but remove your dress and do a slow, 360 degree turn before you sit down.” Donna wanted to see how her Sissy would look and react to being exposed in only her lingerie; in effect she was checking ‘how sissy is my Sissy?’

Nickie removed her purse and hung it on the back of a chair. She carefully pulled her mini-dress over her head and placed it neatly on an empty chair. Before turning around Nickie quickly adjusted her seemed stockings and garter belt into place and shrugged her pert breasts into their proper position. Her black three inch heel pumps completed her attractive look. Nickie slowly turned around and allowed Donna to inspect her and her lingerie.

“You did a fine job in dressing as I requested. Your short dress, garter belt and rear entry panties are a nice touch and shows that you are embracing a feminine and perhaps Sissy lifestyle. Your makeup is perfect and your lipstick matches your nail polish. Your hair and arched eyebrows look exceptionally feminine and shows a true commitment to the lifestyle you seek; good job, Princess.”

“We both know that being a Sissy involves more than clothing, makeup and long hair, right? Sissies exist to serve in many ways, including sexual; but Sissy’s have needs, urges and desires that needs to be fulfilled, correct?”

Nickie nodded in agreement.

“Have a seat Princess and some scones and things and a bit of tea before we move on to more enjoyable things.”

Tea and company

Donna poured a cup of tea and slid the cup and saucer to where she wanted Nickie to sit. “Care for a scone, Sissy?” Nickie took a finger sandwich and sipped her tea.

Begged to be Pegged

Nickie had scheduled losing her virginity in a safe environment so she would know what to expect as she expanded her Sissy and feminine lifestyle to include more intimate activities. She wanted to be inseminated and learn how to better serve and pleasure her Mistress and partners.

Donna wanted to ease Nickie’s apprehension about what engaging in intercourse could involve; it’s very unsettling to see a Sissy cry.

Donna thought Nickie needed to experience a gentle first fucking by a considerate penis in order to round out her Sissy education. 'It’s best that I breed her first before some brut of a leather-boy in a truck stop parking lot or in the back room of an adult book store hurts her; I'll be doing her a favor' Donna reasoned. After all it was Nickie that had made the appointment.

As Donna poured them more tea she engaged Nickie in idle conversation to help distract her brain from the day’s activities; a first fuck should never be hurried.

“You look very at ease in wearing bras and panties; your legs look magnificent in those stockings; I can tell this is not the first time you’ve dressed up; your bracelets were a nice addition to your wardrobe and the pushup bra is perfect for a Sissy.” Pointing at Nickie’s chest Donna asked, “Is all of that you!?”

“Yes, Miss Donna. Although I don’t consider it ‘dressing up’ I wear female clothing on a daily basis; I sleep in the most beautiful and feminine sleepwear that I can afford. I keep my legs and body smoothly shaved and I always wear lingerie under my boy clothes; I like boys that that like boys like me.”

“Did my Sissy princess fantasize about being a cocksucker as a young lad, long before meeting me?” Donna asked.

Nickie lowered her eyes and demurely nodded her head in the affirmative and softly confessed, “Yes Miss Donna, I sucked my first cock when I was 12 years old and have never stopped; I enjoy having a penis between my lips and I love toying with it with my tongue. My first boyfriend taught me how to pleasure a cock but he never fucked me with anything but his fingers which I thoroughly enjoyed; I occasionally pleasured my pussy with battery powered vibrator. I feel like I’m missing out on something very special; I’ve missed out on being filled and fucked by the real thing.”

“How many times a week do you masturbate darling?” Donna asked.

“I first masturbated at 11 years old and have never stopped; I play with my clitty when the need occurs or when I think of you.”

“Oh?”

“Since I first sucked you off I’ve dreamt about you and your cock; I loved feeling you throb and ejaculating in my mouth and I love the taste of your sperm. When I masturbate I dream of being fucked by you. I’ll be your devoted Sissy if you’ll have me Mistress Donna!”

Donna pondered Nickie’s erotic comments a moment and said, “Nickie dear, a first fuck should never be hurried, Sweetie. I think we should start with you giving me the best blowjob you’ve ever given.”

Donna led Nickie to the living room.

Donna walked to an overstuffed Queen Ann chair that had a matching footstool and two side tables. One table held a box of tissues, baby wipes and several small pillows and the other had a small serving tray with condoms, Pearl Lite tampons, lube and a single tube of lipstick. Donna spread a large absorbent towel on the chair cushion and turned to face Nickie; she beckoned Nickie to come closer.

“Remove my panties Princess so I can sit down and watch as you pleasure me.” Nickie’s heart skipped a beat upon being referred to as ‘Princess’; it reminded her of home. Princess Nickie did as she was told and after inhaling the odor of Donna from the panties Nickie neatly placed them on one of the side tables. Nickie watched, enthralled, as Donna’s penis began to come to life.

Donna described

Donna’s crotch had been covered by a skimpy matching string bikini panty. Where a boy-bump should be was womanly flat; Donna had obviously been well tucked.

Four satin garter straps held up sultry 5 denier seamless showgirl stockings; each garter tab was accented with a femininely delicate pink bow. 4 inch black patent leather high heel pumps completed her feminine look.

Donna’s sparse makeup consisted of smoky eye shadow, eyeliner, superbly arched eyebrows and showgirl false eye lashes. Her high cheek bones were accented in a moderately heavy evening dinner party blush and bright red lipstick made her cupid bow lips standout. Her lipstick matched her perfectly shaped long fingernails. Donna’s complexion was flawless.

Donna’s long blond hair was pulled back into a perky no nonsense ponytail. Donna’s pierced ears sported two inch gold hoop earrings; a delicate humming bird charm made of colorful gems on a delicate gold chain hung around her neck.

For being born a man Donna made an exquisitely beautiful woman. Such a special woman is in high demand by many.

Nickie felt fortunate to be alone in the presence of Miss Donna. Nickie was a one person fan club of Donna’s beauty and her acceptance for those living alternate life styles; specifically the queer community.

It begins

Still standing Donna gripped her nakedness, closed her eyes and stroked her shaft with well practiced ease to a hardness that she preferred; Donna smiled as she spread her slippery pre-cum all around the good places. Nickie’s licked her lips in anxious anticipation of tasting the nectar beginning to ooze from the tip of Donna’s cock.

Before sitting down Donna tossed a pillow on the floor at Nickie’s feet. She sternly said “Kneel, Sissy!” Nickie replied with a meek “Yes, Miss Donna” and quickly complied; Nickie’s excitement and the bulge in her panties was growing.

Donna sat down and stared at the cock-sucking Sissy that was kneeling at her feet. She extended one leg and commanded, “Remove my pumps.” “Yes, Miss Donna.” Donna then extended her other foot and the process was repeated. After kissing the sole of each of her warm stilettos Nickie neatly placed Donna’s red soled Louboutin’s next to her chair and out of the way and awaited Donna’s next command.

Donna smiled and waited a moment to allow the tension to build. Picking up the tube of lipstick from the serving tray Donna leaned forward and handed it to Nickie; “All my Sissies know what to do next.”

Nickie extended the lipstick and without a mirror deftly coated her all ready red lips with a sluttier red and moved closer to Donna’s urgent erection. Maintaining eye contact Sissy Nickie took hold of the base of Miss Donna’s cock with one hand and cupped her dangling she-sacks with the other; Nickie lovingly massaged Donna’s hairless pearls; that unexpected move by Sissy made Donna gasp in delight.

Nickie was kneeling between Donna’s wide spread stocking covered legs and was anxious to suck her penis deep into her mouth. After licking the clear dew drop from the tip of Miss Donna’s cock Nickie politely kissed the tip, making sure to leave a red mark, and leaned in to engulf Donna’s cockhead and shaft; Donna abruptly slapped Nickie’s eager hand; Nickie recoiled and waited for Miss Donna to speak.

Donna extended an open hand and asked, “Aren’t you forgetting something Sissy boy?” she asked.

Momentarily taken aback Sissy ‘wannabe’ Nickie blushed and said, “Please forgive me Miss Donna I was preoccupied and had totally forgotten my stud fee payment. It won’t happen again.”

Nickie reached into her bra and retrieved a folded £20 bank note and placed the money into Donna’s outstretched hand. Donna smiled, accepted her fee, tucked the note into her bra and leaned back into the chair; the warmth of Nickie’s body heat on the note felt nice against Donna’s breast. “Thank you Princess, you may continue. I’ll be sure to spurt you an extra bit of my ‘dream cream’ if I can.”

Kneeling between Donna’s wide spread legs Nickie sensuously sucked Donna’s engorged penis fully into her mouth as proof of her Sissy submission; leaving red ‘love rings’ on Donna’s cock was very exciting to Nickie.

Feeling Donna’s stockings on the sides of her face as she fellated her added to Nickie’s arousal level as she lovingly bobbed up and down her mistress’s shaft; she gently tugged on Donna’s garter straps as she orally worshipped her hard cock.

In an attempt to prove herself worthy Nickie used the tip of a finger to caress Miss Donna’s sensitive perineum as she sucked her shaft. Nickie briefly stopped her efforts long enough to ask “Please lean back and tilt your hips a bit Mistress… I need a better angle.” Donna looked quizzical but complied.

Princess had more than a blowjob on her agenda

Donna leaned back in her chair, tilted her hips and raised her legs placing her stocking covered feet on the edge of her chair. Using one of the nearby small pillows she tucked it under her pelvis giving Nickie the angle she had requested. This move also caused Donna’s legs to spread further apart.

Nickie boldly switched from using her finger on Donna to using her tongue and lips to tease and caress the two inch perineum ‘strip of pleasure’ that ran between her anus and scrotum.

It gave Nickie great pleasure to kiss, rim and penetrate Donna’s puckered anal ring with her talented tongue. Donna began moaning in sexual ecstasy at this unexpected but greatly appreciated sex act. Nickie continued to tongue-fuck and stimulate Donna’s love hole.

After Nickie had probed and kissed Donna’s boy-pussy to her heart’s content she immediately raised her head and resumed giving Donna the best blowjob of her life.

When Donna’s moaning and involuntary thrusting became almost uncontrollable Nickie deftly buried her middle finger deep into Donna’s boy-pussy and began finger fucking her in a rhythm that made Donna squeal with delight. Donna loved it and began moving her hips in a way that pleasured her inner core.

Nickie made sure to artfully massage Donna’s prostate to maximize her pleasure. Nickie was hoping that her unexpected sexual ministrations would increase the volume of creamy warm sperm that would soon be hers. Nickie often referred to ejaculation as “lover’s yogurt”.

Within minutes Donna’s groin and penis convulsed in sexual pleasure; her cock and hairless sack of pearls ejaculated torrents of the honey sperm that Nickie had dreamed about; she sucked, slurped, savored and swallowed as fast as she could. Princess was in such heavenly bliss that she spontaneously spewed several gratifying loads of her own love sauce into her red satin panties. She was glad that she had brought a spare.

Nickie stopped fingering Donna’s boy-pussy but left her middle finger embedded as she enjoyed the involuntary gripping on her finger that intense sex brings; Donna had an amazingly strong anal ring muscle that undoubtedly pleased her lovers.

To Nickie’s delight as she sucked on Donna’s cock she emitted additional intense ejaculations; the sheer volume of Donna’s sperm began to overflow from Nickie’s bulging cheeks. Donna was fully spent and begged for Nickie to stop; Nickie reluctantly stopped her blowjob and removed her soiled fingers from Donna’s love hole; she cleaned her finger with a nearby baby wipe. Donna had ejaculated much more than the extra spurt of sperm that she had promised Nickie earlier.

Donna collapsed back into her chair and Nickie collapsed on the floor at her Mistress’s feet just as she had dreamed of… just as it should be.

"A pleasure delayed is a pleasure enhanced"

Nickie had hoped to be mounted doggie style or perhaps bent over a chair and shagged to orgasm today but getting laid would have to wait. Like the good Sissy she was Nickie put her dream on hold and continued what she loved doing; leisurely tonguing and sucking Donna’s most intimate parts. Donna did not object.

After Donna had recovered from her sexual reverie she put on her panties and had Nickie standup so she could hug her; this was an extremely unusual event. After Donna had hugged her new Sissy for an appropriate amount of time she kissed Nickie passionately on the lips and used her tongue to probe Nickie’s mouth. After a few moments Donna broke their kiss, smiled and said, “Tasting myself on your lips thrills me!”

Nickie’s efforts earns her a gratuity for services rendered and a job very well done

Donna patted Nickie on her pantied ass and handed the £20 bank note back to her. “You earned this Princess but sadly your fucking will have to wait an hour or two. I want to fuck you the right way and I need time to recover. Perhaps another cup of tea will help.”

Nickie smiled coquettishly and quipped, “For obvious reasons my belly’s a bit full now but a cup of tea would be very nice and a trip to the kitchen and the potty will allow me get a fresh pair of panties from my purse.” She followed Donna back to the kitchen grabbed her purse and asked to use the restroom.

Donna had a well appointed bathroom room that had a variety of lotions, makeup and mouthwash. While Nickie sat, peed, refreshed her makeup and gargled, Donna brought a tray of tea and snacks to a comfortable love seat in her living room. Donna placed the refreshments on a coffee table and took a seat. A moment later Nickie sat down beside her; their hips touched.

As they noshed and drank Donna said, “Princess you definitely have Sissy qualities and tendancies but I am beginning to believe that you are not a Sissy and that you are even more special; Nickie, I believe you are a pretty, talented, gay man with a womans brain.”

Nickie tilted her head quizzically, took a sip of tea and said nothing. Looking at Donna it appeared she was in deep thought.

After a pregnant pause Donna smiled, held Nickie’s hand and asked, “Would you care to spend the night with me Nickie? I have a pale lavender Gucci wedding night peignoir set that you would look absolutely delicious in.”

Having said that Donna leaned over and kissed Nickie for an extended moment sensuously on the lips, stood and encouraged her to stand also. Holding Princess Nickie’s hand Donna led her to her bedroom.

As they walked Donna spoke, “I’ll have my car drop you off at your flat tomorrow… would a 2 PM drop-off work for you?” she asked. Nickie nodded her head in the affirmative: she was pleased at the way the day (and night?) was going.

As they walked, Nickie lovingly caressed Donna’s satin covered butt with her left hand; in her other hand was the tampon “cork” that Donna would need to fulfill her promise; Nickie wasn’t taking any chances.

End of a beginning

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