It was a calm autumn day, the type of lazy day that takes one’s mind off of the world and lets it wander. This was no exception for Jesse Ignatio, whose thoughts had turned to the finality of fall and its romance.
Romance was a common thought to Jesse, who had often thought himself a romantic, an incurable lover of the world, but never of those in the world. He was himself a bit eccentric about his love endeavours, for he never pursued the normal type of girls, even though he was quite handsome and women found him very appealing. With brown hair and bluish green eyes, his Italian roots won out over his less significant Spanish heritage, although they complimented each other nicely. He was never out of style and certainly never out of date, but he did so effortlessly, never consulting fashion magazines or watching the trends. He was just naturally on top of the world.
But the women he enjoyed were far from feminine; he pursued women who worked in careers like construction, women who worked hard and often scoffed at his living, that of a high school literature teacher.
Even so, he struggled on. After labouring for many years, he decided that he needed a new sense of identity. At thirty-two, he knew that he had wasted too much time trying to get what he thought he wanted.
Sexually, Jesse found himself less and less turned on by the large breasted women that he sought out to fulfill his ever-growing needs. Willing to try anything, he sought out other less traditional fantasies- interracial, anal, transsexual, and the list went on. Finally, fearing that heterosexuality could be the barrier he was trying to break, he broke down and rented a gay porno with a twinge of shame.
He was rolling in it. He loved seeing the men lick each other and caress each other.
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He practically came (without manual stimulation) when one man shoved his very erect penis into the other man’s anus. He had never before been turned on like this.
He quickly shut off the tape and sat on his couch, wondering what he would do next. Something still didn’t feel right. He didn’t think he was gay. It just couldn’t be.
Glancing at the clock, he realized that he had been thinking for well over an hour and decided he would sleep on it. He quickly undressed, deciding that it was much too warm of a night to put on any clothes. As an afterthought before he shut out the light, he wondered if it would be any easier being a woman. No pressures of having to choose the right girl; after all, he would choose you. No more need for sexual domination, which he had always felt was more like a chore in bed.
He quickly dismissed these thoughts and turned out his lamp.
At around 2 a. m. , he woke to a strange sensation.
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He realized that he could not move his arms or feet and struggled to see what was restraining him. Seeing nothing, he attempted to move his torso. His efforts were fruitless; he realized that he was utterly paralyzed and helpless. He thought to scream, but what he saw next made him speechless.
His vision became blurry at first. He had never needed glasses or contacts, but he was having difficulties even making out silhouettes. All of a sudden, his vision focused, and as he looked down at his body, this is the sight he saw:
His body was starting to change, like a liquid filling a new container. His torso started to quiver and sway vertically, and he noticed that his body was beginning to become narrower. He felt his spine snap sharply, and although he felt no pain, he felt his hips assume a different position altogether. His legs were now wider apart, and he began to feel a premonition of what was happening to him.
He saw his member, which in reality had been a decent seven inches, more than enough to please any women he had the chance to encounter sexually. Now, his organ was shrinking before his eyes, making the blood rush out of his face. It finally disappeared with a pop, but he felt it continue to shrink.
Meanwhile, his torso was assuming its shape, narrowing sharply at the stomach and waist. His greatest surprise was his chest ; it was now growing , and when it finally stopped, he realized what was happening.
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He was transforming into a woman.
His adrenaline soared as he felt his insides changing; he could feel his testes growing into beautiful ovaries, and he imagined all of his male organs morphing as a caterpillar becomes a butterfly.
Finally, in the last throes of his transformation, he felt himself rising to orgasm. He felt what was his most intense pleasure to that day, and as he knew he was going to explode in an array of sweat and exhilaration, he felt his vocal chords twist, and he screamed.
As a woman.
He- she- knew that it was over. Jesse Ignatio was no more.
She lay in bed, her muscles still twitching from the mind-bending orgasm. She felt her muscles finally relax, and she lifted her arms, which were now free. She sat up and breathed in deeply.
She was here. This was what she was meant to be.
All the struggles as a man, all of the awkwardness- it was the way she was supposed to know what she was meant for.
She knew she could not wait any longer, but her new body restrained her again, and she fell asleep, dreaming of the ecstasies she would or Jessi, as she now thought of herself- woke to the sunrise shining in the Venetian blinds that she had always admired. She rose from her canopy bed, which had always been a laughing matter to the girls she had previously brought to the room, and strode to the kitchen.
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She then made herself a three-course breakfast, eagerly awaiting the day ahead.
She was grateful for the timing; her transformation had taken place in June, with classes having given out only for a few weeks. She would have plenty of time to explore herself before she would have to face her job, if she would ever be able to go back.
Jessi decided that the first thing would be to find some better attire, since all of her clothes were Jesse’s- she now thought of Jesse almost as a past existence. She put on the most gender neutral clothes she could find and went down to the department store. She found that she was a modest 36C cup size, which she was thrilled to find. She now fit into a size 4, and she was able to wear a women’s size 7 shoe. She purchased 5 outfits, as well as several pairs of panties and bras. She also visited a beauty salon, where she had a manicure and pedicure, as well as having her hair styled.
Having gone back to her house to try on the outfits, Jessi felt a pang of desire- she wanted to find out the other feelings she could experience in her body. Slipping her now manicured hand down her panties, she rubbed her index and middle fingers against her very erect clitoris and sighed deeply. She leaned back on her bed, spreading her legs wide and twisting her fingers around her clit and pussy. Practically dripping with her own natural lubrication, she inserted one, then two, and finally three fingers deep into her cunt, moaning deeper with every thrust. After only a few minutes, she bucked her torso forward and yelled out in squeals of pure pleasure.
Lying back on the bed, she decided that this was not enough.
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She wanted to be fucked, and she would not stop until she had accomplished it.
Her atomic clock on the wall read 6:59 p. m. , and so she picked out her most sensual outfit, a black sheer dress with inch heels and a black leather purse to match. She hopped in her Jetta- also a object of ridicule as a man- and zoomed off to the night club downtown.
The night club, appropriately named House of the Ebony Sky, was a hotspot for singles who wanted to dance and sweat and get hot with other attractive singles. Jessi was fully aware of this, and she knew that if she was going to get fucked tonight, it would start here.
She opened the doors to the club, and she saw a few heads turn. Her Italian and Spanish roots were still evident, and she was now so drop-dead gorgeous that Jesse himself would have been shaking in his boots. In her sexy attire, she knew that guys were already getting hard-ons, trying to shake them off in front of their girlfriends or crushes.
Her eye had already spotted the one she would fuck tonight; a man stood at the bar, sipping a gin and tonic and scoping out tonight’s digs. Little did he know that tonight’s digs were already scoping him out.
Tony, a middle class paralegal, was a booming success; his firm was putting him through law school, which he was excelling in and hoping to reach the top of his class. His efforts won him many friends in his office, but his gregariousness stopped there. He was a dismal failure with women, although, like Jesse, he had a classic beauty that most women admired, even though he was romantically inept.
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Jessi strutted across the floor, and strutting is no exaggeration of terms; she had practiced what she thought of as her "I want you" walk and was milking it for all it was worth. Tongues were wagging and she shook her stunning body over to the bar next to Tony.
"Hi, I’m Jessi. What’s a cute guy like you doing over here alone at the bar?"
"Waiting for the right girl to break through my shell, I guess, Jessi. By the way, I’m Tony. "
"Whatever your name, I don’t care, because you’re the sexiest man in this club. "
"My, aren’t we forward? But please, no more flattery; I can’t stand the praise. "
"You are quite the modest one, Tony. Care to dance with a lonely young lady?"
He smiled at her and said, "Only because you asked so nicely. "
The pair took to the floor and danced like two lovers, intertwined and melded together like two forged pieces of metal. The heat rose as the two took over the floor, pushing all others out of their way, finally building until the entire club was clapping and yelling.
Finally, Tony realized what a scene they were making and pulled Jessi to the side.
Over the din of the party resuming, he yelled at her ear, "Do you want to go back to my place so we could maybe get better acquainted?"
She nodded furiously and grabbed her purse, practically pushing him out the door. They hopped in his BMW and zoomed off to his apartment downtown.
They reached the door, and as he fumbled for his keys, Jessi rubbed her hand across his chest.
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She felt his heart beating a mile a minute, and she knew that he was hers. She was going to get her fuck.
Tony finally unlocked the door and pushed it open furiously. He flipped on the light switch, and she saw his apartment, which was surprisingly similar to hers. She felt immediately comfortable, and she prodded him to sit on his spacious leather couch.
After getting positioned close together on the couch, Jessi kissed Tony’s cheek and moaned quietly in his ear, "When’s the last time a woman ever rubbed you all over your body?" He nervously whispered, "N-never," and she replied, "Tsk, tsk, you’ve been mistreated far too long. "
She unbuttoned the top button of his dress shirt- as an afterthought, she considered that Jesse owned a shirt like this- and massaged his chest gently. Tony exhaled deeply, and Jessi reached for his face with her other hand. She pulled him forcefully but gently to her waiting lips and kissed him deeply and passionately. He leaned into her kiss, finally sticking his warm tongue into her mouth, just as she had wanted him to do.
He then reached over and grabbed her breast, kneading it and massaging it until he found her ever-sensitive nipple. Jessi squealed in delight, and as she threw her head back in ecstasy, he squeezed her tender aureole, sending sparks throughout her body.
While Tony was making his move on her, Jessi felt her desire building up. She didn’t know how much longer she would last before she threw herself on him.
Fortunately for her, it wasn’t long for Tony.
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He had been wanting to fuck her ever since she spoke a word to him. She was a gorgeous brunette, although her hair was so dark that it was practically black. Her figure was superb, and she was sexy as all hell; so what did she want with him? He didn’t even care to find out; he just wanted her now.
He broke the embrace abruptly, and in the most gallant way he could think of, he picked up Jessi into his arms and carried her swiftly to his bedroom. Jessi was amazed to see another sight- a four-post bed with canopy- but her thoughts quickly turned back to Tony. He had now unzipped the back of her sheer dress, and as she stood, the gown fell to the floor, exposing her large but still contained breasts, her delicate waist, and her gorgeous ivory legs.
Jessi then took to finishing unbuttoning Tony’s shirt and ripped it off him, revealing a chiseled chest and firm abs. Before she could lust much more, she bent down and thrust open his belt, then unzipped his pants, and finally pulled his trousers to the floor. The two were now down to underwear, and they resumed their embrace.
As they broke their kiss again, Tony grabbed the sides of Jessi’s face and asked, "Why are you doing this? You could have had anyone back there. "
She met his stare and said, "You were the only one I wanted to make love to. "
They kissed again passionately, with Tony fumbling to remove Jessi’s bra. After accomplishing his task, they simultaneously removed their last pieces of clothing, and now stripped down to the bare, they practically tackled each other to the bed and started caressing each other sensually.
After a few moments of discovering each other, Jessi pushed Tony onto the bed and said, "I want this to be more than just a fuck. I want to give you what you want.
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"
She then took his erect penis- a humble seven inches- and shoved into her waiting mouth. He gasped in surprise, and she felt his cock surge with excitement. She sucked his phallus eagerly, licking and savoring the sweet taste of his rod. She sucked as hard as she could, feeling his hips thrust up into her tight little mouth. Finally, she felt what she had been so ready to enjoy; he started panting furiously and thrusting harder up into her. After a few seconds, she felt the sweet taste of his cum fill her mouth, and she sucked it all until he gasped and felt back on the bed. Having swallowed the better part of a cup of his semen, she started stroking his now withering penis until it resumed its hardness.
Feeling like she was ready to explode herself, Jessi repositioned herself until she felt his head rubbing against his clit. After waiting a few seconds in anticipation, she drove her pussy down on his rock hard cock, making sure not to let it all enter her. She knew that she would most likely still be a virgin after this transformation, and she wanted to make sure she enjoyed losing her virginity.
Tony, meanwhile, was about to die of pleasure. Jessi had planted herself on his cock, and she was riding gently up and down. He could feel the resistance of her hymen and almost couldn’t believe his luck- he was fucking a virgin! It was almost too good to be true.
Jessi felt the time come, and as she rode down on his cock, she drove down hard and felt her hymen rip inside of her. She screamed as she was swept with a wave of pain and pleasure mixed together, and as the wave passed, she drove down harder.
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She moaned and yelled, "Oh, Tony, I am so glad you have me first…oh, baby, fuck me hard, fuck me any way you want…"
Tony did his best to stay conscious as the beautiful vixen bucked on top of him. He didn’t want this fuck to end, but he knew he wouldn’t last much longer.
Finally, as he felt himself rising to orgasm, he yelled out, "Do you want my cum, Jessi?"
She screamed back, "Oh, yes, baby, give it all to me! I want your hot cum shooting all the way up inside of me!"
They both moaned as they felt the final throes of the orgasm coming on. Finally, Tony squirmed and thrust intensely as Jessi felt gallons of Tony’s hot cum filling her sweet pussy.
Tony’s thrusts subsided, and Jessi pulled off of his cock with some reluctance. Her virgin blood was running on his sheets, and his cock was crimson with its glow.
Tony broke her stare by pulling her head to his and greeting her with an intense, powerful kiss. They both collapsed into a deep woke up the next morning and did her best to clean up the mess. She knew that the sheets would have to be replaced, and she almost considered asking Tony if she could have them as a memento, but she decided against it, thinking that her memory would be enough to sustain her passions for a while.
But, if they didn’t, she certainly had some place to turn.
.
