All In

ALL IN

Robert begins a new life and a first-time experience with a Trans Goddess.

This new story is a wonderful fantasy that has been gaining a great deal of traction and wishful thinking of late. All the characters are midlife (well over the age of 18) and consenting adults.

I have a few story lines started and wondering which would make the best series to continue writing future episodes. If you enjoy this story and interested to see it become a series, please leave a comment to that effect. A nice 5 star rating is always greatly appreciated. Thanks.

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Robert had just moved from his previous life. A major change from having been in a longtime heterosexual marriage. But due to realizing and agreeing that their lifestyle, sexual preference and interests had manifested to such wide extremes, it was time to start a new beginning.

Lenora, being very conservative and devout heterosexual, wanted children for so long, but despite all kinds of attempts at fertilization with Robert, unfortunately, nothing worked.

The decision was mutual and after 17years of marriage the breakup was cordial to say the least. Lenora came from money...lots of money... and provided Robert with a very sizeable lumpsum payment in lieu of alimony. As well the family added a beautiful penthouse apartment in an ideal location for what he wanted to do with his new life. Lenora's family strongly suggested that it would be best for all if the divorce was final and done with as quickly as possible. They coached Lenora and she finally agreed, that it was so much more convenient and timelier to provide for him than deal with lengthy divorce proceedings and having their lives drug through the mud...I mean court.

You see, Robert had always had a very strong feminine side, and perhaps was what Lenora, initially, was attracted to about him. He was always so sensitive, so soft and tender, always so sweet and polite.

However, as the years passed and his femininity became much more pronounced, she wondered what happened, and how his behavior had deepened to such a great extent.

He found he was happiest when he could freely express his gurliness in very feminine attire and gestures, spending his time fussing about his looks, doing yoga and Pilates daily, shopping for leggings, jeggings, nice lacy or silk panties and jewelry. How much he enjoyed cooking, baking, and gardening instead of fixing things, or participating in hardcore sports. Both Lenora and her family were embarrassed and often appalled at his sissy behaviour.

When it came to being full on gay, Robert never really considered he was, nor had ever indulged in affairs with other men, but definitely on a few occasions, it was obvious to others, that he became more than aware and keenly interested when an attractive male, that also had a feminine side, came into the room.

Now having the freedom to indulge in whatever pleased him, he decided it was time he could and should explore that side that had been so much a part of him since his adolescence, yet held back while trying to conform to the expectations of his marriage and "straight life".

The new penthouse suite was located in one of the country's highest regarded "gay friendly" neighbourhoods. Most all the shops and community events were run by and specifically catered to LGBTQ citizens.

Within a couple of weeks, the move was taken care of and he was all settled in his new place. Such excitement to start a new life...so many things he was looking forward to, and in periods of deep thought, he found he could get so aroused just thinking about pretty men, athletic men, men in feminine attire...sissies? ...Yes even sissies dressed up in frilly dresses, maid uniforms, in panties, stockings, garters, high heels, and all the attractive sexual behaviour that he had missed out on for almost 2 decades.

He decided since he was about to begin a whole new life, that it was also time to dawn a whole new look. He found a small hairdresser shop not far from his place, and made an appointment. He always had a thing for David Bowie, his music of course, but also his look and his hair style. Very handsome!! His own hair was very similar, a light sandy brown and he had the high cheekbones and the longer chin...he could almost do a "Bowie look".

On making the appointment the lady at the front counter said she could book him on the next Saturday, at just after noon. "You know that's Pride Day don't ya? There are big community events, a parade and lots of stuff going on that day so we will be closing early. If you get here around noon, I'm sure Tisa can fit you in. She's very good at that style. "

Over the next few days, Robert continued enjoying the sights on the streets, the clear openness to androgynous styles of clothing, makeup, jewelry, bright colours, and the vibrant sounds of the "Gaybourhood". There was so much to take in.

On the day of his haircut appointment he woke up a lil' late, had a quick shower and headed straight to the shop. He got there just at noon, and there was a steady shuffle of people just leaving, ...all sporting a wide variety of styles.

"I think I found what I was looking for" he muttered to himself as he walked in the door.

As he approached the front desk, the same lady, greeted him, "Oh I was wondering if you were going to show up" with a flirty smile. Looking down at her screen... "Robert? Is it?"

"Sorry I slept in a bit."

"No worries! Take a seat if you please and Tisa will be right with you. You're the one that wanted the Bowie style, right? "

"Yes!! How nice you remembered!" replies Robert with a big smile.

Robert took a seat, and it was only about 5 minutes till a very tall black lady approached the foyer, and looking straight at him...asked "Robert?"

The front desk lady reminded Tisa, "Ok, yous' will be the last to leave, so remember the doors all lock behind you... and a reminder to please be sure and set the alarm before you leave...Ok Tisa dear?"

"For sure! I got this Girl!! See ya later this aft at the parade or the party?"

"For sure! ...annnnd I'm outa here...gonna be a great weekend of fun!!" Replied the lady at the desk.

Robert followed Tisa to her workstation which was in the back of the shop.

Tisa had a big smile and lovely tightly braided dreadlocks

piled high into a ponytail. She wore a white nurse like frock, with white thigh high sheer stockings, and corked high heel sandals. A white lace hem stuck out the bottom of the frock.

Tisa was well endowed both with her warm smiling pretty face and manner but also, she was very curvy.

In Robert's quick getaway from the apartment he dressed very casually, in his favourite pair of Lulu Lemon lavender blue leggings which fit very tight to his thin frame, and especially his ass. He threw on a pinky/white short sleeved lady's silky T shirt, that was cutoff short at the bottom to expose his abs.

"Come over here hon,...have a seat right here ...and ..tell me what style ,.. exactly, were you looking for in a Bowie cut?" With a big smile!

"There are different styles of Bowies?"

"Of course darling, ...let's see there's .....the punk cut, which he painted or dyed pink and sometimes even orange , (laughing) or the long brush back look, ...". As she demo'd with his hair.

"Yeah the punk look was what I was going for..'cept without the dyed colour please!"

Smiling Tisa replied, "ok, great! Very popular, ..and it looks like you have the perfect hair for that"...as she began combing his hair back. "Very nice! Thick and satiny. Then again after a few moments "You have very nice hair Robert, and I agree, its a beautiful colour, ...very close to his natural colour, at least as far as we know,..it's fine just the way it is!"

"Do you mind if we give it a bit of a shampoo...before we get started?"

"Not at all! ...I am all in" conceded Robert!

"Ok we're just gonna recline the chair and I will get the shower head wand"...with that she reclined the chair till Robert was almost horizontal... she then pivoted the chair so his head was pointed downward towards a sink. As she turned and reached for the shower head...Robert got a quick peep up her skirt. He could see Tisa's beautiful lace stockings attached to white garters and overtopped with a beautiful white lace thong panty. A very large package was partially tucked.

As Tisa soaped and lathered his hair, he would catch more glimpse shots of her beautiful black body contrasted in white lace lingerie. These memorable views confirmed that Tisa was Trans...and absolutely gorgeous!

Robert had frequented Trans and Gay porn sites and had fantasized about having a Trans experience one day, but never thought it would be possible. Now with his new life in a completely new setting that encouraged and supported the lifestyle, anything was possible.

Still searching for the right person to have his 1st gay sex encounter in over 20 years, it didn't take much to make him very horny. He reminded himself to focus on thinking of anything else, to try to keep his bulging cock from giving him away.

However, the outline of his growing erection was becoming very evident in those tight lavender leggings.

Tisa was used to this. Robert wasn't her first "Bob in the shop"...so continued with confidence ...and light conversation.

"Are you looking forward to the parade?"

"Oh yes, of course... it will be my first time! I'm excited to see all the dress ups and great looks, ...I haven't decided what to wear myself, just yet.. I do have a nice pair of pleated pants and matching jacket...ya know if I was gonna do the whole Bowie thing... he chuckles.

"Ahhhh, ..first time?.... Huh!...yes that outfit will definitely go well with this hairstyle....you'll look just like him, ..when I'm done." Smiling warmly, looking down at him while she combed and trimmed.

"So you are new to the community?"

"Yes, recently divorced, and lookin to make a fresh start here!"

"Hmmm, interesting! I've been here about 10 years now, ..and have found it's very friendly, I really like it here. I'm sure you will too!"

She lowered his chin and leaned in close so she could trim his top hair...giving Robert a direct view of her beautiful cleavage. Her breasts were at least a 42D and she carried them high .. the areoles just hidden inside the cup of her corset cups. The scent of her perfume was intoxicatingly delightful.

Robert was taking it all in ...like a schoolboy his heart quickened...and he could feel the warm blush of arousal. He could feel his cock now stretching down his right leg inside those lavender blue leggings, ... it twitched occasionally.... He felt a bit of precum soil his leggings.

Tisa continued with her work, all the while, with an occasional glimpse at his growing third leg, enjoying the view.

The shop was now completely quiet.

As she finished up...and spun him around to look in the mirror...he smiled and was amazed how he was now a David Bowie look alike....

"Wow, I'm very impressed .... I think I just need a lil makeup" remarked the new Robert Bowie.

"Oh you aint seen it all yet darlin, ... for another few bucks, I could do your make up too?? Bowie, always had a lil rouge on his cheeks and gloss on his lips, a lil eye shadow, ...hmmm?

"Really.... You'd do that for me? That would be awesome, thank you ...for sure!... let's do that. I've always wanted to have someone professionally do makeup on me."

"Baby, there's a lot more I could do for you.... professionally, ....as she spun the chair around so she could look him straight on.... She leaned her right hand on the counter, and the other slid up his leg. Her perfectly manicured white fingernail traced the outline of his erection, with just the spandex of his tight leggings separating them.

"Looks like you might be feeling a lil pressure right here...and all along here.... I could take care of that for ya too, darlin.....there's nobody here but you n me...and if you were to promise to leave a nice tip,...Well, I would just love to take care of all of that for you."

Robert looked up to her beautiful black complexion and her big beautiful eyes, her nice thick eyelashes ...batting at him. She put her hands on her hips and pushed her huge tits out in a pose that was absolute killer. Her frock was now opened at the top, no longer able to contain the buxom load that lay within.

"Oh my God, I can't believe this is happening", replied Robert with his mouth wide open, ..almost drooling, and breathing deeply.

With a little teasing laugh, Tisa says, "Ok.Mr. Bowie, let's get this party started!"

With that she pushed a button under the counter... and Bowie' s "Ch Ch Ch Changes", began playing through the sound system. The door to her workstation closed, and cupboard doors opened with surround mirrors everywhere.

Tisa unbuttoned the top of her frock, revealing a beautiful white sheer see through lace corset bustier and the top of her beautiful big breasts.

Robert gulped down air in awe, as she undid the rest of the buttons down her frock to reveal the white lacey petticoat skirt portion of her corset dress.

She grabbed the waist hem of Robert's leggings, "Butt up off the seat, please", she demanded...and she pulled his leggings down to his ankles. Robert's rock hard cock, was sooo inflated with anticipation, it twitched a couple times up and precum formed at the head. He had never seen his cock this hard before, all the while his mind was focused on what he had seen underneath that beautiful white lace petticoat corset dress, that incredible huge black cock.

"Oooo what have we got here, ..a nice early gift"...as Tisa's long thick tongue slithered and slurped its way up his shaft and took in the dribbles of precum flowing down his frenulum.

"Mmmm love precum...don't you?"

She than swatted his cock against her tongue several times and stroked it with her left hand. She took his swelling mushroom head in her thick lips, and went all around the head, tonguing underneath in little circles as she went, then slid her plump glossy lips down and then back up the shaft.

Not only was the sensation driving Robert wild, but Tisa was so absolutely beautiful...he was so turned on by her. It was like he had taken a double dose of Viagara. The veins on his cock looked like they were ready to pop. He never had this happen in his marriage.

"You are so beautiful Tisa! Could I please see the rest of your beautiful body? I have never had an experience like this...I'm both very excited and very nervous all at the same time. I'm not sure what to do..."

She smiled and turned around slowly...and undid the clasps in front holding the dress on...she turned back towards him while slowly opening the two sides to reveal her huge 42+DD cup breasts which were perky and standing out. Her areoles were huge as well as her nipples. It was too much for poor Robert to take in all at once...his cock looked like it was about to explode while it stood straight up and twitched in little circles, while more precum emitted out the top. But his attention was now fixed on the huge black cock that was struggling to stay inside Tisa's lace panties.

Tisa gave it a quick tug to release it from the immense pressure of containment. It popped out and it's thick shaft a lil bent and crooked at first.. started to straighten out, it's foreskin slowly retracting back, while it headed straight towards his face.

"Oh my God", gasped Robert, I've never seen anything like that!! It is so lovely. Can I please have a taste?" He asked, his eyes like a puppy dog looking up at her.

Tisa smiled, and leaned closer towards him...."yes, of course you may", as she pushed her thumb down on the base of her shaft to point her huge thick cock into his mouth.

It was so big! This was finally it! ... years of fantasizing about sucking another man's cock, and now finally coming to fruition in such a dramatic way!

As he stared at the head just inches from his lips, almost purple, he sooo wanted this. He stretched his neck to take it in.

Robert struggled with getting his lips around it at first...but he opened as wide as he could and was able to take the swollen mushroom head into his mouth. Robert tried with everything he had to take more of that beautiful black cock into him... Tisa moved around to stand over top of him, moving to at back of his head.

She slid him up in the chair so his head and neck fell over the edge of the headrest, and now her magnificence was pointed straight down his throat, ...all while she continued to stroke his cock and then bent over and took it down her throat in one full gulp. She swallowed him whole and then stroked him with her tongue and with her firm grasp at the base of his shaft, she could feel that all this might be too much! She didn't want to finish him just yet... so she pulled her lips off the top of his cock with a pop...and then stood over top of him and did everything she could to make it easier for Robert to suck, slurp and slide his tongue along her huge cock and try his best at pleasing her.

As his focus remain dedicated to providing his absolute best, his thoughts reflected for a moment to the 20 years plus of having to keep it all inside, and now finally satisfying a whale of pent up sexual anticipation with such a grand opportunity, Yes!!, He was a fucking sissy, guilty of being gay, and now at long last....glorious freedom to be sucking the hugest black throbbing cock that he couldn't .....even imagine.

Robert's exuberance was a high, ...a huge high ...high on sex, for the first time in years... his ferocity and loathing for this long-awaited experience exemplified his commitment to pleasing Tisa. How he adored her massive cock, her huge tits, her beautiful body wrapped in white sheer and lace, how fortunate he was to have this amazing experience. This is how sex is supposed to feel.

Both his hands rubbed Tisa's long shaft, lubed with precum, stroking, stroking while sucking, licking, slobbering over her beautiful cock. He tried desperately to swallow her head and pushed the physical nature of his throat muscles to allow it. The sounds of gagging and gluck, glugging in the back of his throat were self-fulfilling, and he began to hum like he was savouring the most delicious desert on the planet. He looked up at her as he kissed the head of her glans, holding her mighty shaft with both hands, running his tongue under and licking, around, then up an down and sucking her as deep inside as he could get it. Meanwhile streams of clear cum continued to run out the top of his cock and dribble down his shaft.

He resolved to maintaining a steady even stroke with his mouth in anticipation of her cum, her precum, her golden juices, he wanted so badly to taste her. Stroking with his hands, his mouth ..increasing his lips grip, on her length in hopes of causing her to release her load.

Tisa was greatly enjoying his enthusiasm, and surprised that this self-proclaimed first timer was doing such a good job. She helped by maintaining a rhythm of thrusts into the back of his throat. She could feel her climax building and was eager to reward his efforts with a rich load of her juices. She began moaning in an effort to help it along and to signal her lover of what was cumming.

She finally reached down with her long fingernails and pulled her nut sack back, while still thrusting, she let go rope upon rope of thick chizzy cream. Her magnificent huge cock slipped out and back into Robert's throat. There was cum flying everywhere...on Robert's face and chin, in his eyes, in his mouth, on the counter and mirrors beside her and some even got into Robert's new Bowie cut.

After several minutes of gasping for air, she had time to slow her panting "Ooooh baby ...you really got my juice flowing... That was wonderful Robert......and now I got a special surprise for you...yes mmm. We gonna get down to some good ass fuckin..."