jakes_choice.html

Jake's Choice
by Pritty Kitty

Based on Caption Ed84 by Ed Miller

“Janet, what’s it like being a woman?” Jake asked my girlfriend as they lay in bed after a particularly hot sex session.

“Do you really want to know, Jake?” Janet asked him.

He rolled on his side and looked at her beautiful face. He had been attracted to her right from the first moment he saw her sitting in his mathematics class. Her blond hair and lovely eyes had been a big turn on. He had sat down at the desk beside her and began a conversation. They hit it off and had been dating for almost a year now.

“Well, yes, kind of. You know me, always curious.” he replied.

She rolled over to face him. “It is incredible. Sure, we have our tough moments, periods, feeling bloated, strange people hitting on us, but for the most part it is great.”

“What about sex?”

“Now that is one of the great parts. Sex with you is great. I love the feeling of your cock sliding into me. My climax is amazing. I don’t know what sex is like as a male but from what I can see sex as a female is better!”

“What about sex with girls?” he continued.

She looked at him closely, “Jake, you know I like girls too. You know I sometimes have sex with my girlfriends but I love you.”

“Yes.” he answered. “I know that. We agreed to that. You know I do not feel jealous about you and your friends. Besides, I have a friend too.”

“Nor I about Jenna! I think we both understand that we are committed to each other but not tied down by each other. Jenna realizes that too from what she tells me.” Janet said to him as they lay face to face. “Some day, if we decide to marry we will have to re-examine this and decide where we want to go with our open relationship. But that isn’t what you asked, is it?”

“No, I know all that. I just want to know if sex with women is as satisfying as with men?”

“It’s different, Jake. It can be very satisfying and before you it was often more satisfying. Most of the guys I had sex with were less than great so my female friends were often a source of pleasure. You have been the exception.” Janet told him lovingly. “I adore our time together both in and out of the bedroom. So, I guess sex is great for us women, it is for me at least. If the person is right I can have several climaxes and still be ready for more.”

She looked at him and saw how much he cared about her. His eyes always got a bit watery when they talked like this, hers too. She did love him very much and from the very start she had. He was different than the other guys she had dated.

“Jake, why are you asking me this?”

Jake looked at her and debated telling her about his deepest fantasy. They had been together for a long while now and he felt extremely comfortable talking with her. He knew she could keep a secret and he knew he could trust her but this was something he wasn’t sure he could share.

Janet saw the thoughts cross his face and wondered why he was concerned about telling her something she knew was probably a very deep secret. No, actually she knew why he was finding it hard to tell her. He had probably kept it in and deep for so long that the thought of telling anyone was difficult. She touched his cheek gently.

“Jake, please tell me. We know each other very well. We understand each other and our respective desires, let it out!” She whispered to him.

Jake stared into her eyes and saw the reassurance there, “I don’t know if I can, Janet. I have kept this secret so long.”

“Tell me!” She whispered.

Her whisper reached down deep inside his head and broke down the defenses. It felt like he was compelled to tell her. He told her that he had experimented with cross dressing back in high school. He told her that every time he had worn women’s clothing he had dreamed of becoming a woman. The desire was there even now. He wanted to know how it was to be female. Janet smiled to herself as everything she had felt with Jake became clear to her.

“He may be a big burly guy but he really is a sweetheart, so gentle and kind and willing to fulfill all my desires and needs.” She thought to herself. “He has a strong feminine side to him despite how he looks. Hmmmmm!”

He told her that once he graduated high school and began going to college he had stopped wearing women’s clothes. Joining a frat had killed any further chance of cross-dressing.

“Sometimes I just do not feel comfortable with who I am and with this body.” He told her. “I always picture myself much slimmer and shorter. I kept a picture of a woman I wanted to be like for years.”

So you want to change sexes?” Janet asked. “If I told you I could help you what would you say?”

Jake looked at her in disbelief. “Janet, it can’t be done. I’ve dreamed of it. I’ve thought of it but besides surgery it can’t be done! Look at me! I’m a big guy! Surgery couldn’t change that!”

Janet smiled at me, “What if I told you would look as good as any of my girlfriends and no one would be able to tell that you were once a male.”

I looked at her incredulously, “Make ME passable! How?”

“So you would be interested?” She asked.

“If it can be done, yes, and I can be passable. I would go for it in a second.” Jake said not really believing anyone could turn his 200 pound 6’ 3” frame into a passable woman.

Janet looked at him, “Jake, is it your deepest desire, your strongest wish to do this?”

“Damn right! Now tell me how it can be done?” Jake demanded.

Janet saw a sign of desperation and desire in his eyes. She could tell that he was telling her the truth. She could read him by now and knew when he was not telling the truth.

“Okay,” she said, “Meet me at the parking lot just behind my Sorority House next Friday at 5 PM. I will arrange everything. Bring nothing but yourself. Will you be there?”

Jake thought about it and decided that he had nothing to lose by saying yes. She wouldn’t be pulling his leg and he knew she wouldn’t be setting him up as a joke. She wasn’t like that.

“Okay sure, I will meet you.”

He felt her hand reaching for his cock and slowly stroking it. It felt very good having her masturbate him, her mouth on his cock was even better, and fucking her was exquisite.

Janet leaned over and whispered in his ear, “After Friday you will see that sex as a woman IS much better. I will show you an orgasm like you never had as a man!”

His cock got rock hard at the thought. He heard her chuckle as his cock became rigid and she ducked beneath the sheets. Janet began to suck his big cock into her mouth, giving him another one of her excellent blowjobs. Her tongue on the head of his cock made him squirm with pleasure especially when she put her tongue on the very tip of his hard cock.

She moved her mouth up and down his cock alternately sucking him deep in her throat and letting all but the head slide outside her mouth. The feeling was great and it made him wonder just how much better being a woman would be.

“Ah, if she keeps this up I am going to come into her mouth in a few minutes!” He thought to himself. “I wonder what it would be like if I was in her position?”

As if reading his mind she stopped and crawled back up to kiss him. He actually had never minded when she kissed him after sucking on his cock. The taste was not so bad and mixed with her saliva it was kind of kinky. Janet was about to slide Jake’s cock into her pussy when he wriggled out of her grasp and moved down her body. He kissed and licked his way to her breasts. He spent a long time on each breast and nipple, making her writhe in pleasure before he continued down her body.

While at her breasts he had caressed his right hand down into her pubic hair and then between the lips of her pussy. Jake remembered all too well what Janet had taught him and began to hit all the right places on her. His fingers did what they had done many times before and made her cries of pleasure louder and louder.

“Jake remembers oh so well where to touch me! God, but he is almost female in his desire to pleasure me. Never met a man like him!” She thought.

Finally, Jake slid the rest of the way down and slipped his tongue into her very wet pussy. His licking, sucking, and nibbling made it hard for her not to scream out. Jake continued to bring her to almost the orgasm point before he backed off and let it subside, despite her pleas for him to make her come.

“Jake, oh, please, Jake, fuck me now!” She finally said after he had kept her from several orgasms. “God, I want you inside me. Fuck me with that big, hard cock of yours!”

Then she added as he entered her extremely wet vagina, “Fuck me one more time before I turn you into a beautiful woman!”

That set him off. Janet felt his cock stiffen once more as she said that. She loved the feel of him on top of her. He hit her clit just right in this position.

“God, how could he get any harder?” She asked herself. “He must really love the idea of being female! I have to …. Ah … ah…”

“God, Jake, yes, fuck me with that big cock! Fill my pussy with it!” She breathed into his ear. “Next week, I’ll fuck you with my strap on just like you are fucking me now!”

That sent him over the edge, he groaned and his body stiffened. Janet felt his cock quiver and his head get slightly larger before it pumped his semen into her. She felt the jets spurt into her, that, and his continuing to fuck her made her orgasm shoot through her body. They climaxed together, both yelling out the other’s name as they did.

Once their climaxes were done Jake rolled onto his back carrying Janet with him so she was now on top. He kept his still hard cock inside her allowing her to either continue or to relax and let him slip from her. She slowly began to move her ass and slide his cock in and out of her pussy. She had come but wanted still more of Jake. He wanted more too.

Janet paused for a moment and moved her legs between his forcing him to spread them wide. She looked down at him and lustfully looked into his eyes.

“Soon, Jake,” She told him, “I will be on top like this fucking you with my long hard strap on, pumping it in and out of your new cunt, making you squeal with pleasure as you learn what it is like to be a woman. Do you want that, Jake?”

She began to fuck herself with his still hard cock as she said this to him. Jake panted and nodded.

With increasing lust in her eyes she looked down at him, “Do you really want that, Jake? Tell me now! Come on, TELL ME!”

It was getting to be too much for her and she could see that Jake was almost there too.

He looked up at her, she knew right then she had him, “Yes, Janet. I want to be a woman!”

She smiled, “Why, Jake, why?”

“I want to feel your cock inside me, Janet! I want you to fuck me like I fuck you! Oh god, yes, I WANT IT!” and with that he came again. She continued but his cock was softening.

She felt her climax coming as she continued on his soft cock. It finally slipped from her well fucked and semen full cunt but not before she came and collapsed on top of Jake.

They lay there like that for a long while. Jake’s seed slowly leaking from Janet onto his abdomen. She gathered her energy and slunk down to where his semen was and began to lick it off his body and cock. She sucked his cock into her mouth and cleaned it. Finally, she got up, grabbed his hand and pulled him toward the shower.

“Friday, two days from now!” They both thought as they showered.

The next few days felt like they took forever for Jake and Janet. Janet wanted to see how Jake would handle being a woman. She wondered if he would like it and want to stay female or hate it and want to return to his male self? Jake was dieing of anticipation about the whole change. He wasn’t sure if he was going to have his most secret desire fulfilled or if Janet was just having him on. Either way he knew Janet had something planned because the last couple of nights had been some of the hottest of their relationship.

Finally, Friday arrived and Jake spent the whole day on edge. His buddies kept asking why he seemed so nervous and edgy? He just explained that he was going off for the weekend to an old family friend’s cabin for some fishing and relaxing and was anxious to get going. At last, the time for him to meet Janet neared and he packed a backpack despite what she told him, he wanted it to at least look like he was telling the truth to his buddies, and headed out.

He met her behind her sorority house where she parked her car and they headed off. She told him to relax and that this would be about an hour’s drive so he sat back and let the world outside the car pass by. His mind didn’t focus on the passing scenery but on the events that might occur this weekend. They had agreed that he should try out the change for the weekend and then revert back to his old self on Sunday night if he wanted to.

Silently, Janet had hoped he wouldn’t. She loved him very much but she had decided that she could love him as either sex and her family wouldn’t be too upset about her being in a relationship with a woman. Besides, if they decided to have children Jake could revert back to male or she could make the change. Either way one of them could carry and have the baby and the other could father it. But, that was a ways down the road yet. Right now she was more interested to see how he would react to being a woman.

They finally reached the old house on a hill. It had a high stonewall around most of its gardens and the drive was fronted by an old iron gate. Janet drove up and the gate opened slowly as her car’s lights shone through it and up a small visible portion of the drive. She kept going and the both saw that the drive was a long loop that circled past a wide wood front door. There was a huge knocker on the door but Janet could also see a small, lit doorbell button just to the left of the door. She had been told to use the knocker.

The house itself was big and looked very old. It seemed to have at least three floors but it was hard to tell exactly with the variety of levels it seemed to have. It wasn’t castle like but there seemed to be some similarities. But she knew this already. She stopped just at the front door and got out.

“You can leave the backpack here.” She told Jake. “I brought some stuff you will need. I bought a few items today and I borrowed a few things. You should be all set for the weekend.”

Jake just nodded because he wasn’t sure he would be able to speak he was so nervous and anxious about this whole thing.

“Jake, don’t be nervous! It will be fine and it will only be until Sunday night. So relax.” She said.

Again Jake nodded and followed her up to the door. She raised the knocker and let it down. A loud boom sounded as it hit the brass plate. She knocked twice as she was told and then they waited. She knew someone would come soon and sure enough, not long after the last boom the door began to open.

A beautiful young woman stood in the doorway looking at them. She was dressed in a dark purple mini dress with black stockings and heels. She wore long black gloves on each hand and a black velvet chocker with a gorgeous cameo at her throat. Her long blonde hair glistened in the light from behind her. Jake looked into her eyes and saw they were a piercing blue, almost the blue of a mountain lake. Her lips matched her dress, as did the makeup she wore on her eyelids. The effect was stunning.
“Janet, you arrived right on time!” the woman said to Jake’s girlfriend. He was a bit stunned by this.

“Yes, the drive was pretty quick considering.” Janet replied. “Carla, this is Jake, my boyfriend. He has come here tonight for The Change!”

“Ah, this is the man you told us about! Very well, come in, both of you.” Carla said as she stepped aside to let them both in. “Would either of you like a quick cup of tea before we begin? I think Jody put on some tea for your arrival.”

Jake just nodded, thinking it wise to accept the hospitality offered. His voice was still on vacation though.

In a room lined with books a tall statuesque black haired woman dressed in a short maid uniform was standing beside a small tea table. Jake stared at the woman briefly noting her well-shaped legs encased in black stockings, her black pumps, a small white apron encircled her waist and over a beautiful black miniskirt uniform. She looked like every man’s fantasy. Jake saw her lovely shaped breasts. They weren’t huge but were big enough to make the woman look voluptuous. She worn a velvet chocker around her throat very similar to the one Carla wore. Jake became aware that he might me staring a tad too long so he looked away.

Carla led them into the room. “Ah, Jody, you put out the tea. Excellent! Janet, Jake, this is Jody. She is my in-house maid.”

Jody curtsied and said, “It’s nice to meet you both. Would you care for some tea to relax?”

Janet spoke up quickly, “I think we’d love some.”

Jody poured the tea into 3 small and delicate looking teacups and gave them to each person.

Jake sipped his while Carla and Janet talked. He snuck several glances at Jody marveling how beautiful she looked and thinking how much he’d love to look like her. His mind pictured all the things he would do if he had the chance to be female, even if it was just for a short time. The thoughts made him surprisingly sleepy and the voices began to recede from his consciousness.

A distant voice that sounded like Janet’s called him, “Jake, come on. Shall we go into the other room and change you?”

“Yes, please!” Jake heard himself say in the distance.

Another voice sounded, “Jody, would you please help Jake.”

He felt two small but strong hands grip his left arm and help him to stand. An arm encircled his waist and guided him. He felt himself moving but couldn’t understand where he was going. Finally, he was guided into a softly lit room with a large table in the center.

“Jody, please undress our young man and get him to lie down on the table.” A voice said.

Jake felt Jody’s hands begin to undress him. He saw her long beautiful fingers unbutton his shirt and slide it from his body. He saw her fingers return to unbuckle his belt and undo his jeans. He dreamily watched as his jeans and boxers were taken off him and he was led over to the table. Jody then told him to lie down on it. He did so without hesitation. Her voice sounded so soothing and wonderful.

Jody told him to think of the woman he’d like to be. Her voice sounded insistent so he brought the image of the woman he had always dreamed of being into his mind. She told him to hold that image in his mind. He slowly lost consciousness as Jody moved his arms and legs into position.

Jake awoke with a start. He felt a soft bed beneath him and a pillow below his head. He felt very different. Something was wrong. He no longer felt his heavy 6 foot frame and he felt something on his chest, well, two somethings actually. He moved his hands to his chest and felt two smallish breasts there. His fingers slid over each breast and caused the nipples to harden slightly. His mind registered the pleasure as he tweaked each nipple playfully. He slid his right hand down to where his penis was and found nothing. No penis. His mind finally registered the change.

“HOLY CRAP!” He shouted as he sat bolt upright.

Jake searched his groin and found the soft folds of a pussy there. His mind froze in shock.

The bedroom door flew open as Janet raced in with Carla right behind her. Janet ran to the bed and climbed up beside Jake and pulled him into her arms. She held him telling him she loved him and loved the new him. Carla stood and silently watched.

At last, with Janet’s urging, Jake got out of the bed and walked to a full-length mirror. There he saw the girl he had seen in his head for many years. She was pretty. The girl stood about Janet’s height with smallish but firm breasts and reasonably shapely legs. Her hair was a light brown color with some blond highlights. As Jake turned to look at her backside the figure turned too. He realized that the girl was him. He had been transformed.

“Oh my god, you did it!” He said in surprise and excitement. “Wow! I can’t believe it but you did it. Thank you!”

Carla stood behind him and replied, “You are welcome, Jake. But I want you to remember that this is just until Sunday midnight. You will have to return here if you decide to remain as a woman and if you want to change any part of you. If you do wish to remain a woman your past will change to reflect that. To all your family and friends you will have always been female. They will remember only that.”

“You mean I could stay this way if I wanted to?”

Carla nodded, “Yes, but you have to get here before midnight Sunday.”

“I will get him here regardless.” Janet said as she stepped up beside the new Jake and slipped her hand into his.

She smiled at him in the mirror, “Well, you look gorgeous! Good enough to present to the girls back at my sorority.”

Jake turned to look at her, “Do they know about this?”

A huge smile came on Janet’s face and the familiar twinkle came to her eyes. Jake knew that there was something sexy in store for them later. “Well, 3 of my best friends do and they are anxious to meet the new you. So what should we call you?”

Jake thought about it for a few seconds and then said, “How about Jackie for this weekend? It isn’t my favorite but it is close to my name now so it should do.”

“Jackie, it is.” Janet said with a nod. “I brought you some of my clothes to wear back. We can pack up your old clothes in the same bag. Come on, let’s get you dressed and home!”

Jake saw her mischievious grin return. He knew something was up.

Janet set out the clothes and he put each one on. Finally, he was standing in a short denim miniskirt with a soft pink T-shirt and a pair of short socks. Under the clothes he had on a matching pink bikini panty and bra set. The bra was a bit big but still fit. Janet told him they could get him something in his size later. She pulled out a pair of running shoes and gave them to him. He slid his small feet into the shoes and walked a few steps.

“A little big but the will do.” He told her.

“Well, I think you are ready so, let’s go.” Janet said.
They headed downstairs to the front door and both of them gave Carla a big hug. Jake whispered into Carla’s ear asking her to thank Jody for him. He told Carla that Jody had made him feel comfortable and warm. Carla whispered back that she would.

They drove off leaving the large house with Carla and Jody.

An hour later, Janet pulled the car into her parking space behind her sorority house and got out. She waved for Jake to follow her but he sat there for a minute, his stomach doing nervous flips as he thought about meeting Janet’s friends and the rest of the sorority she belonged to.

Janet stopped and looked back at him as he still sat in the car. She could see his nervousness written all over the pretty face he now had. She walked back to the car and went to the passenger door and opened it.

“Jackie.” She said as she stood beside his seat, “Don’t worry, you are going to pull this off, I guarantee it! Besides, the girls you will meet right now are my closest friends and they are very willing to teach you. It’s cool! Relax. You look great!”

Jake wasn’t so sure but he let Janet take his hand and pull him into the house. It was late Friday night so the house was almost empty and those who remained appeared to be on their way out. Janet introduced him to a couple of passing girls as Jackie her old friend from her hometown, who was visiting for the weekend. Neither girl batted an eye at him they just saw him as another girl. He began to feel more and more comfortable as the girls chatted with him.

Finally, he and Janet got to the top floor of the house. Janet and two of her friends had the rooms up here. They were big rooms, big enough for 2 or three girls in each. Currently, Janet was in a room by herself, her old roommate had had to leave school for some personal reason. They entered Janet’s room.

“Here she is, girls!” Janet said as they stepped into the room. “Girls, I’d like you to meet Jackie! Jackie, these are the girls!”

Three voices spoke at the same time as Jake entered the room.

“WOW! She’s cute!” said Katherine, the blond with short hair.

Sasha, a tall redhead, “Pretty! Jackie, you look wonderful!”

Deanna, a slim girl with dirty blond hair, squealed in approval.

Jake saw that they were waiting for he and Janet to return. They stood and rushed over to him and eyed him up and down.

Deanna asked, “So how does she look under the clothes, Janet?”

“Definitely edible!” Janet replied with a smile.

Katherine began to unzip the miniskirt, “Let’s see. I JUST have to see!” she said with a huge smile.

“Yes, me too!” Sasha joined in.

So the three girls undressed him before he could put up much of a struggle not that he really wanted to because the thought of these women touching him was making his new pussy very wet. They would see that soon enough.

Soon enough Jake’s clothes were on the floor and he was standing in front of the girls naked. They circled him running their fingers over this part, prodding that part, touching another part. Katherine ran her fingers across Jake’s new right breast and nipple. The sensation shot shivers of delight up his spine.

“Oh ho, she likes that!” Katherine shrieked in delight when she saw Jake shiver. “I think she wants more!”

Deanna slipped a finger between Jake’s new pussy lips and yelped , “Wow! She’s wet already! Oh look, Jackie is enjoying this!”

And he was! It was a feeling he had never felt before, strong and intensely pleasurable. He let out a moan as Deanna and Katherine kept going. His reactions became totally involuntary as the pleasure he felt mounted within him.

Janet stepped up and took his face in her hands and began to give him a loving kiss. Their tongues twisted around each other’s tongue. Their lips met and softly lingered. The feeling was very different than when he was a guy, Jake felt. Another pair of hands began to caress his new female body sending more shivers through him.

He broke the kiss and said to the girls, “ I have to sit down before I fall down.”

They all giggled and pulled him over to the sofa. Katherine sat down and pulled Jake down to sit an her left. Janet sat down to the left of Jake, then Deanna. Sasha left the room and went down the hall. The other girls began to pleasure Jake again, running their hands across parts Jake had never had before. He let out little yelps of pleasure as Katherine fingered his clitoris. Janet leaned over and began licking his left breast. Her tongue felt marvelous on his new breast. Katherine’s finger was driving him wild. He could feel his first orgasm as a woman coming. He had never felt anything like this before. It was amazing.

Sasha returned with 5 vibrators, she then handed them out. Katherine took hers and turned it on. The purple vibe began buzzing then she put it onto Jake’s right nipple. Jake moaned as the vibrator sent pleasure waves through his body. Janet turned hers on and began to stimulate Jake’s clitoris with it. More waves of pleasure washed through him. He then found enough strength to turn the pink one he had on and use it on Janet’s pussy.

He looked past Janet and saw that Deanna and Sasha were pleasuring each other with their vibrators. The sound of moans began to drown out the sound of the buzzing machines. Jake’s saw that his nipples were rock hard now. The pleasure was crashing through him. He smiled at Janet as she and Katherine continued to pleasure him.

It was great! His mind buzzed and screamed for more as the pleasure increased. He knew he would come soon.