Trying On Outfits With My Half Sister Laura
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Jamie had a happy early childhood despite the unusual circumstances surrounding his/her gender. As the title of this story implies, Jamie was a boy who was born with a vagina.
After a difficult pregnancy, Jamie’s mother happily welcomed her new-born baby girl into the world. Jamie’s mother, however, conclusively made up her mind that this would be her only child. After months of painful retching, she was determined never to put herself through an ordeal like this again.
By the time Jamie was four years old, the manifestations of her future as a boy began to make themselves known and Jamie would have a shit-fit if her mother even tried to dress her in girl’s clothing.
Over the following years, this trend only ever escalated and her parents simply accepted that their daughter was a tomboy. Jamie’s general behaviour was also boyish and ‘she’ did not display any girlish affectations. All the toys his parents bought for her were the toys that boys would play with, and Jamie only hung out with the boys at school and in the neighbourhood.
Although Jamie’s hair was always short the one thing her mother was pleased about, was that Jamie took to wearing gel in her hair. In Jamie’s mother’s mind, at least the spiky hair on top of Jamie’s head gave her a slightly more androgynous appearance.
By the time Jamie was nearing the end of primary school, and all the kids of his age were entering puberty, Jamie simply remained flat-chested. It was at this point that her mom decided to take Jamie to a psychologist.
The psychologist instantly realized the dilemma facing Jamie, because she had come into contact with a similar case study a few years earlier. As before, she was instantly captivated by Jamie’s predicament. After a few sessions, she also discerned that Jamie was not a lesbian and had no homosexual tendencies. Jamie was simply a boy who was anatomically different. As with her former patient, Jamie was attracted to men.
Playing it safe, the psychologist decided not to jump the gun with Jamie’s mother and advised that they should monitor the situation over the following few months. The psychologist also employed the services of a transgender doctor that she had formerly worked with.
When it became clear that the psychologists and doctors prognosis was accurate, Jamie and his parents were given their final result.
Option one was that Jamie could commence female hormone treatment and become a woman, which both practitioners did not advise. The second and the less likely option was that Jamie could wait a few years before undergoing a female to male transformation, an even less likely choice. Option three was that Jamie could simply accept his situation and live life as a man with a female’s genitals. Needless to say, this was the option that appealed to Jamie the most.
Fortuitously, shortly after Jamie commenced high school his dad was seconded to a branch of the firm he worked for that was in another state from where they lived. When this occurred, Jamie made up his mind that in his new environment, he would definitely live his life as a male.
The psychologist, aware of what lay ahead for Jamie, came up with a very clever solution prior to their relocation. She suggested that the doctor give Jamie a medical note to say that due to a medical condition, Jamie should be excluded from all physical activity at the school. The fictitious reason for this was that Jamie had been born with a heart defect and that any form of exercise could possibly be fatal. This naturally meant that being precluded from any kind of sports activities, he would not have to expose himself naked in any locker-room.
This ploy worked extremely well and for the duration of his high school stint, Jamie was even able to use the toilet facility for disabled students. An added benefit was he was also never bullied. Sadly, however, Jamie’s two new high school buddies who were regarded as total nerds often had to endure the attention of the high school ‘persecutors.’
In Jamie’s final year of high school, a new neighbour moved in next to his parent’s home. Gordon was a furniture maker and made bespoke pieces for well-off customers. His craftsmanship was extraordinary and he always had a waiting list for his creations. Cleverly, Gordon soundproofed the triple garage next door that was his workshop, so that he would not be an irritation to neighbours in the vicinity.
Gordon was a good-looking man and from the moment that Jamie met him, Jamie was totally captivated by Gordon. He was a stud and in the months that Jamie observed him, the ladies came and went on a frequent basis. Gordon simply wasn’t into any form of commitment and clearly liked to play the field.
Jamie’s dad instantly took a liking to Gordon and they would frequently chat. In fact, Jamie’s dad ordered two pieces of furniture from Gordon that he had been meaning to acquire for quite some time. Jamie had very little contact with Gordon but whenever he did, Jamie’s heart would palpitate to such an extent, that he almost believed that his fake heart condition may not be as imaginary as he had believed.
Things came to a head one weekend when Jamie’s parents decided to go on a romantic weekend to a country lodge.
Although Jamie was old enough to look after himself, his parents asked Gordon to keep an eye on Jamie during their absence in case anything ‘went wrong.’ In all honesty, this actually irked Jamie somewhat.
What would follow, however, proved to be heaven-sent.
On that Friday afternoon, after Jamie’s parents had departed, there was a knock on the door. When Jamie answered the door he was surprised to see Gordon before him.
“Listen, buddy, I’m all alone tonight, so I figured that I could do with some company. Would you like to join me for dinner? I’ve got salads and two great steaks,” Gordon concluded.
Shyly, Jamie answered, “I really don’t want to be any trouble.”
“Why would you be any trouble? This is not a marriage proposal bro… its simple dinner invitation,” Gordon stated with a snigger.
“Sure,” Jamie answered sheepishly, before asking, “What time should I arrive?”
“Six-thirty… whatever,” Gordon replied nonchalantly.
When Gordon departed Jamie stood looking at the closed door with trepidation. It almost felt like he had the non-existent heart condition that he didn’t have.
At six-thirty when Jamie arrived, Gordon was barefooted and only wearing a t-shirt and short pants. Jamie had always been mesmerized by Gordon’s large butch hands, but now Gordon’s magnificent feet almost had Jamie salivating. As much as he was looking forward to the evening, Jamie wasn’t sure how he would keep his emotions together.
“Would you like a beer?” Gordon asked.
Not wanting to appear a wuss, Jamie graciously accepted the offer.
The table was set and the salads looked delicious. “Wow, the salads look great,” Jamie stated.
“Don’t be impressed, buddy, I bought them from the local supermarket. The thing is, although I’m good with meat, salads are not really my thing. I’m a meat and carbohydrate kind of guy. I like pasta and potato salads generally. The only vegetable I ever consume is thanks to coleslaw. I hope you are okay with that,” Gordon concluded.
“No problem,” Jamie hastily replied.
In no time the steaks were under the grill and a short while later they were seated at the dining table enjoying their meal. “I hope you like your steak medium, like me,” Gordon inquired.
“It’s absolutely perfect,” Jamie assured him, honestly.
Their meal was great.
Afterwards, Jamie quickly assisted with the dishes before they were seated in the lounge to watch a movie Gordon had hired. It wasn’t the best movie Jamie had ever seen, but it was enjoyable, nonetheless.
After the movie ended I was issued with another beer. “So… are you enjoying school?” Gordon then asked.
“Yeah,” Jamie replied.
“I suppose the girls are all over you,” Gordon said, with a naughty grin on his face.
Before thinking, Jamie stupidly replied, “Actually, I'm not really into girls.”
“Oh,” Gordon answered, before continuing, “Do you mind if I ask you a personal question?”
Jamie really had no option and had to nod his head in agreement, given his earlier faux pas.
“Are you gay?” Before Jamie could answer Gordon continued, “I’m not homophobic, bro, in fact, my favourite cousin is gay.”
“No, I’m not gay,” Jamie answered, before asking, “But why do you ask?”
"Well...the thing is… I hope you are not offended by what I’m about to say… But I’ve always thought you are too pretty to be a guy. If that makes any sense,” Gordon concluded.
“No offense taken,” Jamie replied with a smile.
“So, if you’re not into girls or guys, are you, like, asexual?” Gordon stammered in a confused manner.
“No,” Jamie answered, before asking, “Do you know what a transman is?”
“No,” Gordon replied, looking even more confused.
Throughout his life, Jamie had always had to carry the burden of his condition and the only persons who knew about his situation were his parents. Something about Gordon put Jamie at ease and an overwhelming compulsion to vent his secret overcame him.
“Do you have a computer?” Jamie then asked.
“Sure, it’s over there,” Gordon answered pointing to the sideboard in his dining room.
“Please put it on and I will show you something that will explain my situation to,” Jamie suggested.
Gordon did as he was told and shortly, Jamie located the site that he wished to show Gordon. After vacating the chair he was sitting on, he told Gordon to take a seat and click on the play button. As Gordon started to watch the video, Jamie returned to the lounge and sat on the sofa facing away from Gordon.
In the video there was a good-looking naked guy sitting on a comfy chair that was placed at the foot of a large king-sized bed, facing away from the bed. The room was elegant but sparsely decorated. Shortly, the good-looking man commenced toying with his very impressive dick.
Next, a beautiful young guy, only wearing boxer shorts, came into view. The newcomer had a lithe body with a light dusting of chest hair. His face was also covered by facial hair that looked like it was four to five days old. The young guy then got to his knees and started giving the seated man a blowjob.
This was not really the kind of thing that Gordon was interested in, but having been asked to do so, he continued to watch.
After a minute or so of sucking the seated man’s dick, the young guy stood up before pushing his boxer shorts down. Gordon almost fell off his chair as he saw the vagina between the young guy’s legs.
Following that, the young man moved forward and placed his legs on either side of the seated man. After cupping the young man's arse, the seated guy commenced licking the pretty pussy before him. The look of ecstasy on the young man’s face was breath-taking. As Gordon watched he got the most incredible boner of his life. ‘Christ,’ he thought, ‘this is fuckin hot.’
After the reciprocal fellatio episode, the young man moved to the bed and opened his legs in a welcoming gesture. After another brief cunnilingus session, the stud with the impressive cock began fucking the young man. The video ended with the stud shooting his load over the young guy’s pussy.
As Gordon got off his chair to retrieve two beers from the refrigerator, he wondered if he hadn’t witnessed some kind of trickery in the video he had just watched. ‘Surely, such a thing is not possible,’ he reasoned to himself.
As he sat beside Jamie and handed him a beer, he asked, “Are you like the boy in the video?”
“Yes,” Jamie answered.
Jamie then went on to explain his life story, finally culminating in the finding of the two doctors, and their options. Throughout Jamie’s revelation, Gordon sat transfixed, with an incredulous look on his face.
When Jamie’s explanation finally ended, his eyes became moist. “I am so sorry to have troubled you with my shit. It just that… Well, the only other people who know about my condition are my parents. We are a very small family and I never see my other relatives. In their minds, my mom and dad simply have a daughter. You are the only other person I have ever told.” With that, the floodgates opened and Jamie began to sob.
Gordon instantly drew Jamie closer and embraced him. Although Jamie’s parents had always been very affectionate, the warmth from Gordon was far more exhilarating. It was unconditional and very amorous. The stroking caresses of Gordon’s hands felt heavenly.
Gordon had also never felt such a thrill before. He had bedded plenty of females and had always enjoyed sex. This, however, felt different. It was as if Jamie had entered a secret chamber that Gordon had never known about. Gordon felt like a treasure hunter who had just located a gem of immeasurable value.
Overcome with lust, Gordon was unable to restrain himself a moment longer. As Gordon’s hand grasp the back of Jamie’s head, his lips zoned in on its quarry and assailed Jamie’s mouth. With his body now pinning Jamie’s smaller frame, Gordon commenced an intensive kissing session.
Although the force of Gordon’s action caught Jamie off guard, Jamie was totally compliant. Jamie had fantasized about a scenario of this sort for so long, that he would willingly have allowed Gordon to brutalize him in any and every manner imaginable.
When their mouths finally separated, Jamie broke the tension by saying, “Well, I suppose I better be on my way. Thank you for a great evening.” Jamie wanted more but decided to play it safe.
“You’re not going anywhere,” Gordon replied, before continuing, “You showed me that video for a reason, didn’t you?” Jamie did not reply but Gordon could see that Jamie’s eyes were alive with excitement. “You’ve watched that video many times and dreamed of that happening you, haven’t you?”
Jamie shyly nodded his head in agreement.
“Well, now your fantasy is about to happen,” Gordon announced.
After Gordon stood up he grabbed hold of Jamie’s body and placed it over his shoulder, before marching through to his bedroom. Once there, Gordon lowered Jamie’s body to the floor and told him to strip down to his underpants. After doing so, Jamie observed Gordon moved a chair that he had in the corner of his bedroom to directly in front of the foot of the bed, just as they had seen in the video. Gordon then removed all his clothing. As Jamie continued to watching him, Gordon sat down on the chair and commenced toying with his cock.
Gordon’s engorged dick was just as impressive as the man in the video, and after a moment or two, he instructed Jamie to approach and kneel before him. Jamie felt like he was in a trance as he got to his knees and began to suck Gordon’s cock.
For the following few minutes, Jamie performed oral sex to the best of his ability. Having never done so before and given Gordon’s endowment, Jamie was very impressed by the boy he had seen in the video and realized that he had a lot to learn. Gordon, however, was enthralled by Jamie’s commitment.
As Gordon looked at Jamie the thought that crossed his mind was that in his entire sex life, nothing stranger than this had ever happened to him before. Inasmuch as he didn’t doubt that Jamie had a pussy, as the old saying goes; “Seeing is believing,” and when Gordon finally told Jamie to stand up and remove his underpants, Gordon was bristling with anticipation.
The sight of Jamie’s vagina almost took Gordon’s breath away. The combination of having a boy and girl merged into one person was mindboggling. Again, Gordon’s mind questioned how anything like this was possible.
“Are you sure you want to take things further, Jamie?” Gordon asked, with trepidation.
“Yes,” Jamie replied, before silently mouthing the word, “Please.”
“Are you sure, baby,” Gordon affirmed.
“Yes,” Jamie whispered.
Gordon was so worked up at this point that all he could think about was throwing Jamie onto the bed and fucking the life out of him, but resisted the urge.
“Straddle me, like in the video,” Gordon commanded.
After placing his hands securely on Jamie’s backside, Gordon told Jamie to tilt his body backwards. No sooner had Jamie done so, before Gordon’s tongue commenced lashing at Jamie’s portal. Nothing could have prepared Jamie for the pleasure he now felt. The intensity and warmth of the stimulation were completely mind-blowing. Jamie was so overcome with excitement that he began to feel that his non-existent heart condition may actually be real.
As his body shook, his hands gripped hold of Gordon’s head, like a falcon greedily taking hold of a pigeon. The elation for both was mesmerizing.
Shortly, Gordon wanted to explore Jamie’s pussy more vigorously. After placing Jamie’s body slightly backwards, Gordon rose up and after pushing the chair aside, told Jamie to lie on his back on the bed. Their visual contact now became intense and as Jamie had seen in the video, he pulled his legs upward and outward, inviting Gordon to ravish him. Gordon dove straight in and his tongue went into overdrive. He licked up and down and prodded in and out as his onslaught gathered momentum. When Gordon finally used his lips to nibble on Jamie’ clitoris, Jamie began hyperventilating with his hands frantically clasped the bedding as Gordon’s strong hands firmly pinned him down.
As Jamie’s began yelping in ecstasy Gordon feasted on his portal like a starving creature, and when orgasm struck, Jamie experienced the most mind-blowing rapture of his entire life.
Gordan had also never been more turned on in his life. He had always surmised that there was something different about Jamie and had even thought that if he was gay, Jamie would be at the top of his list of preferences. This, of course, was a silly notion up until now, because what was happening to Gordon was way beyond his comprehension. He momentary wondered if he was in the twilight zone but after glancing at Jamie’s pussy once more, assured himself that this was actually happening. An even more compelling thought, however, was that his dick simply had to nest in the portal that he saw before him.
For Jamie, although the entrée’s had been spectacular, the long-anticipated main course could not be served too quickly. As Gordon moved up onto the bed, Jamie’s legs moved up and backwards in an inviting gesture. With their eyes locked in unison, Gordon commenced rubbing his dickhead in the valley of pleasure awaiting him. Unable to hold back any longer, Gordon began to plunge his cock into Jamie’s pussy.
The infiltration by Gordon was not very comfortable but unbelievably rewarding. Jamie’s entire existence had built up to this point and he wasn’t about to devalue it in an inconsequential manner. Jamie loved being a man but he knew that in the bedroom he would always be a woman. Jamie was completely at peace with this trade-off and welcomed the ‘agony’ with open arms.
As Gordon’s hips went into overdrive, the escalation of pleasure became overwhelming. As Jamie started groaning and Gordon commenced grunting, their coitus soon reached fever pitch. The fulfilment that both of them felt when Gordon finally unloaded, was simply beyond description.
After Gordon collapsed onto Jamie, he asked, “Was that as good as you had imagined?”
“No, Gordon, that was even better. In fact, it was fuckin awesome,” Jamie replied.
Gert
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