A Safe Space Ch. 01

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

The softness of Alex's body, the feel of her small breasts, her sleek satin blouse, the hem of her skirt tickling Monika's wrist as she reached under it to grasp the throbbing appendage encased in satin, nylon and lycra, the scent of Alex's perfume and the taste of her makeup was a beguiling combination. A beautiful young woman who possessed a large penis... how could Monika resist such temptation.

The fact the gorgeous young woman was her brother dressed as a girl only inflamed her desire for forbidden fruit. Alex had no idea what she was doing down there but she had somehow instinctively opened the folds of Monika's snatch and was pressing two fingers into her cleft and rubbing Monika's slinky tights on her labia and occasionally brushing her clitoris.

Monika softly squeezed Alex's cock, feeling the heft of it, impressed by its girth, and she began to slowly stroke it causing Alex to moan as the silky fabric of her panties and hose grazed her sensitive organ causing another release of pre-ejaculate that soaked Alex's already wet panties. Alex's tongue writhed in Monika's sweet mouth, and she held her sister tight, encouraging her to keep stroking her quivering organ. Feelings of blissful sensuality were building and Alex could feel her orgasm simmering deep inside her, waiting to erupt as she pressed her fingers deeper into Monika's cleft.

"Oh god!" Monika gasped as Alex's fingers grazed her clitoris through the spandex tights.

It was delightful but it was frustrating.

Monika let go of Alex's cock and hooked her thumbs in the waistband of her Lorna Jane tights which were moulded to her buttocks and legs and forced them down her thighs and kicked them off exposing her freshly shaven pubis and long tanned legs. She took Alex's hand and put it between her legs and wrapped her body in Alex's warm soft embrace and kissed her deeply as she reached for her sister's cock.

Alex explored her sister's sex with her fingers. It was moist, warm and intriguingly fleshy, the outer folds opening to reveal smaller delicate inner folds that guarded the entrance to her vagina. She experimentally pushed a finger into the tight, sultry hole and was rewarded with a gasp from Monika and then a purring sound from deep within Monika's chest as Alex's thumb found Monika's clitoris and pressed on it.

Monika pushed down on the front Alex's underwear, bunching her pantyhose and panties down so that Alex's erect penis sprang free. She grasped the hard sleek appendage and squeezed it and was rewarded with a mewling groan and a pulsing throb from Alex's penis. She could feel the string of slippery pre-ejaculate dangling from the tip of her sister's cock.

Then Monika committed the ultimate taboo.

She guided Alex's penis to her succulent furrow and steered to the entrance of vagina.

Alex froze. The feeling of her cock pressing on her sister's forbidden vulva was unimaginably gratifying and carnal but it was also unquestionably wrong. The warm fleshy folds of Monika's labia seemed to lure in Alex's phallus as they clung to her shaft. The glans of Alex's penis was inside Monika's vagina and her soft spongy flesh clutched at the sensitive corona. Such feelings of wonton delight and forbidden pleasure were compelling as much as they were venal.

"This is wrong Monika," Alex whispered.

"I know Alex," Monika replied and thrust her crotch into Alex's and jumped up and wrapped her legs around Alex's waist.

She clung to Alex. Her arms wrapped around her sister's neck and her legs locked around her waist as Monika impaled herself on Alex's long thick cock, kissing her passionately, her tongue wriggling in Alex's mouth.

Alex felt her sister's cunt envelop her throbbing organ, clasping at her engorged flesh. The steamy maw quivered as the concentric rings of Monika's slippery, spongy clunge seemed to milk her penis. Monika's orgasm was shattering. She clung to her sister, pressing her body against Alex's, wanting to feel her heart beating wildly though her blouse as Alex also orgasmed, filling Monika with a flood of hot musky seed that dribbled from her vulva and ran down her thighs.

Alex felt the most delicious raw sexually gratifying feeling well up from her engorged phallus as it throbbed deep in her sister's tight plush vagina. Alex returned her sister's frenetic kisses and began to thrust her cock in and out of Monika's steamy hole.

Monika was steadily climaxing. Circlets of delight had radiated from deep in her vagina as soon as Alex's cock slipped into her buttery cunt but when Alex actually began to fuck her, her glans pounded Monika's G-spot and her pubis pressed on Monika's clitoris.

Alex staggered over to the big bed with her sister clutching her, hanging on for dear life as multiple orgasms wracked her body. She lowered Monika onto the bed and began to fuck her, Alex's cock still engorged despite having just ejaculated. The feel of the slinky pantyhose on her legs, her satin panties caressing her buttocks, the hem of her skirt tickling her thighs, the taste of her lipstick and the scent of her perfume was overpowering. Alex wondered why she had denied herself this pleasure for so long.

Monika was sobbing, her legs wrapped around Alex, her crotch rising up off the bed to meet Alex's thrusts as yet another orgasm struck her, causing her to mew and moan and her body to shake as she felt Alex ejaculate a second time deep in her bruised, sensitive cunt. This woman lying on top her, her body so feminine and her face so pretty, while she ravished Monika with her long hard thick cock invoked a devastatingly sublime sexual sensation that she didn't think was possible. The fact that it was her sibling only intensified the pleasure.

Alex was spent. Her first sexual encounter had been overwhelmingly resplendent. Being dressed as she was, her feminine persona appropriating Alex's body and replacing his psyche with her own. The only vestige of masculinity being the organ between her legs with which she had ravished her sister. Alex had never felt so gratified but also so guilty.

Alex had fucked her sister. Alex still thought of herself in feminine pronouns and she felt entirely womanly but what did Monika think? Had she just fucked her brother dressed in drag or did Monika think of Alex as a woman?

It was too difficult a conversation to have and with little encouragement, Alex slipped off her heels, her skirt, blouse and bra, leaving on her pantyhose and panties and Monika shimmied out of her spandex crop-top so that she was naked.

Alex used the bedside remote to dim the lights and close the curtains and Monika went to fetch a bottle of vodka, ice and two glasses. Monika giggled as she snuggled under the covers and pulled Alex into a warm embrace. Her sister was erect again. Was she insatiable? Monika intended to find out.

Monika spent most of night educating Alex in the art of lovemaking until they finally fell asleep in the early hours.

Just before she fell asleep Monika realised the enormity of the sins they had committed and she prayed silently to a god she didn't believe in to forgive her.

*****

Monika Dupree sat in the cocoon of seat 1A as Qantas flight 81 thundered down the runway at Kingsford Smith Airport. She'd drunk two glasses of champagne prior to take-off and had drunk four gin and tonics in the Qantas Executive Lounge before she boarded but she couldn't drink away her shame.

She had used the first class around the world ticket pre-purchased by her father as a graduation present and had obtained seats on the first leg of her planned journey that morning whilst Alex was still in a deep sleep. The crushing guilt of the incest they had committed weighed heavily on her. After the unbridled lust she had felt fucking her brother/sister had dissipated, the enormity of what she had done crushed her like a giant stone.

Monika had packed lightly; she would buy clothes as she travelled. She was still ghosting her friends and her boyfriend Bradley who had sent a series of phone texts and DMs on her socials alternately begging her then threatening her to let him come see her. She couldn't face him and intended to break up with him anyway so running away without sending him any messages suited her even though she knew it was cowardly and cruel.

She would DM her girlfriends once she was in a better frame of mind. Her real concern was what to say to Alex. She had left Alex a DM telling her that she was taking a well-deserved around the world holiday and not to worry; she would send socials from each place she visited. She made no mention of their incestuous melee or of the crushing guilt she felt.

As the flight levelled out the flight attendant brought Monika a gin and tonic as requested and she only managed to finish half of the drink before she was in a deep sleep as QF 81 soared over the Simpson Desert.

Alex woke up late and lay in bed thinking about the previous day. She could feel that she was still dressed in her pantyhose and her orange satin and lace panties and a satin negligee. She could taste the lipstick on her bruised lips and smell her perfume. She could feel the stickiness on her semi-engorged phallus and smell a scintilla of Monika's vaginal secretions.

The feeling of being totally feminine had not left her; she was still Alexis the girl not Alexander the boy in her head. She surveyed the purchases still scattered around the huge bedroom. She and Monika had not had time to put them away in their haste to feminise Alex. What followed was both surprising and amazing. Did Alex feel guilty about it? Yes; undoubtedly. Did Alex enjoy it and want to do it again? Yes; undoubtedly.

The house was eerily quiet but it was Sunday so there were no staff in attendance but Alex expected to hear Monika rattling around the house and the sound of her music. Maybe she was wearing headphones? But the place felt empty. Maybe she had gone to meet her girlfriends or Brad. How would they react if they knew what Alex and Monika had been up to? Brad would throw a fit because he was insanely jealous of Monika. But they would never know. The 'sisters' had sworn each other to secrecy. Both their lives would be ruined if the scandal ever came to light. Alex wondered if Monika would be up for doing it again. She definitely wanted to but she was also terrified of the consequences were they to get caught.

As teenagers are want to do, the first thing Alex did was to reach for her phone. She smiled when she saw the red acrylics glued to her fingernails; she and Monika had gone all out. Her phone vibrated when she picked it up indicating that she had messages waiting which was unusual for Alex because she was such a loner.

It was a DM from Monika and Alex was at first confused and then she had an inkling of what had really happened. Monika had always intended to go traveling during her gap year and had told Alex that the only reason she had delayed her trip was because of her concern for her brother and the need to summon up the courage to ditch Brad.

Her sister was experiencing post-coital regret which was understandable. It must be incredibly confusing for her. Monika had basically diagnosed her brother's gender dysphoria, helped her to transform from Alexander into Alexis and then had succumbed to forbidden carnal desires. It was probably good that Monika was away from the house while she came to terms with what had transpired.

Alex however was in a completely different frame of mind. Transforming from Alexander to Alexis had freed her and given her newfound confidence and purpose. She intended to use the safe space of the Rose Bay mansion to live her life as she now believed she should. She would perfect her femininity and live full time as a young woman in the confines of the house until she was ready to announce her transformation to the world.

She shucked out of her soiled panties and ruined pantyhose and took a long leisurely shower then put some fresh pantyhose and panties and sat at the vanity and did her makeup and fussed with her hair. The expert hairdressers at Alana Kristian had given her a shag-cut that was easy to maintain but looked great. She slipped into some lycra leggings and a loose silk blouse and slipped on some cherry-red pumps and carefully walked downstairs to the kitchen to make coffee.

This was now Alexis' house. She had it to herself and it was her domain. Of course Gloria the housekeeper would still need to keep the place spotless and Carlos the groundsman would tend to the gardens and the pool but Alex was mistress of the house.

*****

To say that Brad Brody was pissed at Monika Dupree was an understatement. How dare she ignore him! Monika had seemed distant and distracted recently and although she had not withheld sexual congress he could tell that her heart wasn't in it. He sensed that she was about to dump him. He knew about the around the world airline ticket that she intended to use during her gap year and he had even proposed that he accompany her on the first couple of legs of the trip but she seemed reluctant.

Brad had to spend part of the break between semesters at university working with his father at the company's headquarters in Newcastle where one of their main shipyards was located. Brad didn't think much of Newcastle but the small city was only a two and half hour drive from Sydney so Brad could go home for the weekends.

What really pissed him off was that he suspected that Monika was going to dump him. Not that he would be heartbroken. He had already shagged two of Monika's close girlfriends and had his eyes on another but he wanted to be the one who dumped Monika. But before he did he wanted one last shag. Monika was pretty, had a great body and knew how to fuck. She whined when he asked her to pamper his fetish and asked her to wear sexy lingerie and high heels while they shagged but she sometimes agreed to do it to shut him up. She was a great girl but he was done with her but it needed to he who broke up with her... but not before he had fucked her in the ass which was something she hadn't allowed him to do so far.

None of Monika's friends knew where she was and she was not active on her socials. Brad guessed that she was holed up in her house, probably with that creepy fag twin brother of hers. Maybe he would make an unannounced booty call and then he would dump Monika before she dumped him.

Yes... that was a good idea. That's exactly what he would do!

To be continued

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
10 Comments
newford9bnewford9b3 months ago

the start of another great story from a talented storyteller. 5 Stars all day long.

MeghanBMeghanB3 months ago

Out Fucking Standing. What more can I say! As a married lifelong crossdresser, I've made lingerie love to wife dozens of times over the years, but my secret fantasy is to meet a genetic woman who loves pretty sexy public going CDs and suck and fuck them all day, then maybe move in together and live as girlfriends or sisters.

Someday maybe

jrrtolkien420jrrtolkien420almost 2 years ago

OMG what a great start. I love the way you write. Thanks again for a great story.

VincepetroneVincepetronealmost 2 years ago

Seems like something was to be continued in the story line. Abrupt ending to this chapter.

AnonymousAnonymousalmost 2 years ago

Did this story have page two and three. I read second part of story but I think something was missing

Show More
Share this Story

READ MORE OF THIS SERIES

Similar Stories

My Feminine Side Guy becomes a beautiful sexy girl.in Transgender & Crossdressers
The Agency Mike finds a job, which may be much more than he expected.in Transgender & Crossdressers
Feminized By My Mother Ch. 01 Shemale mother makes son a sissy.in Transgender & Crossdressers
Like Mother, Like Sissy A sissy learns he is a princess . . . and a sperm whore.in Transgender & Crossdressers
A Slut is Born Young man forced to be a womanin Transgender & Crossdressers
More Stories