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Girl's Night
by Rogergirl

Jesse stood naked before his girlfriend Becky.  Jesse was a 19 year old college sophomore.  He stood 5'8" and weighed 130 pounds.  He had a slim, slender body with not much muscle and not a very visible Adam's Apple.  He hadn't had a haircut in a while so his blonde hair was pretty long and rested on his shoulders.  

His girlfriend stood looking him over.  They had been dating for six months now, but Becky had noticed they had grown distant and at times she felt ignored.  Jesse often complained how long it took Becky to get ready when they went out, or would seem preoccupied when she tried to talk to him.  She often caught him checking out other girls when they went out and would often rush through sex.   Despite this she knew she did not want to break up, she just wanted to get him to appreciate her more, so she hatched a plan to get him to understand women better by spending a night as a woman.

"Well, you look about my size," she said, "go take a shower and remove your body hair while I pick out your outfit for this evening."

Jesse reluctantly obeyed and went into the shower and rubbed a hair removal cream over his body.  He watched in shock and all his body hair washed down the drain.  Then he applied the moisturizer and washed his hair.  When he was done he stepped out of the shower and dried himself with a big towel enjoying the feeling of his now soft hairless skin.  He wrapped the towel around himself like a girl and wrapped his hair with a smaller towel as Becky had directed.  

He stepped back into the bathroom and saw some stuff laid out on the bed.  Becky wasted no time and began to transform Jesse.  She tucked and taped his penis back and had him put on a latex vagina she ordered off the internet.  She also attached a pair of realistic breast forms then used makeup to blend the edges.  When she was finished they looked as real as her own.  Next she had him step into a pair of blue thong panties then put on a matching strapless bra.  Jesse tried to look at his transformation in the mirror, but saw Becky had covered it.

Next, Becky dragged Jesse over to the vanity and went to work painting his nails, blowdrying and styling his hair, shaping his eyebrows, and applying makeup.  

After she was satisfied and Jesse's nails were dry she pulled him over to the bed where she had him put on a light blue minidress.  The dress was strapless and came to mid-thigh.  Then she had him put on a pair of 5" heels.  To complete the transformation she put on earrings, a silver chain necklace, and sprayed some perfume.

"Well, are you ready to see how you look?" she said.

Jesse stood up hesitantly and stumbled over to the mirror.  Becky pulled away the sheet and Jesse stood speechless.  Looking back at him was a sexy girl with wavy blonde hair and a perfectly made up face.  Her luscious breasts were displayed prominently at the top of her tight dress and her legs looked long and shapely in the heels.  He could not believe the transformation.  

"So what do you think?" Becky asked.

"I can't believe this is me," Jesse answered still in disbelief.

"Well maybe now you'll understand why it takes me so long to get ready," Becky replied, "but the night is not over yet, we're going out."

"I can't go out like this," Jesse said shocked, "what if someone recognizes me?"

"Don't worry, you look like a hot girl, no one is gonna realize who you are, even I don't recognize you like that," Becky answered.

Becky, who was dressed similar to Jesse, handed Jesse a purse then said, "Come on we have to stop somewhere first."

They went downstairs and headed to the college ID office where Becky worked.  She had Jesse sit down and smile as she took his picture.  Then she went in the back and returned a few minutes later with an ID card and handed it to Jesse.  Jesse looked at it and saw his pretty face and instead of Jesse Daniels, he saw the name Jessica Martin.

"Tonight you're a girl," Becky said, "so you're gonna use that ID to get into the parties we're going to."

"Parties?" Jesse asked.

"Yeah frat parties," Becky answered, and remember for the rest of tonight you are Jessica, so remember to act and sound like Jessica tonight."

Becky and Jessica left the ID office and began walking to the frat houses.  Although awkward at first, Jessica began to walk more comfortably as they neared the frat house.  

When they got to the door they showed their ID cards to the guy at the door and he let them in, checking them both out as they walked past.  They walked into the party and more guys began to check them out, making Jessica feel uncomfortable.  Becky noticed this and handed her a beer.

"Relax," she said, "forget about Jesse and try to have a good time being a girl tonight."

They sat down on a couch and drank a few more beers.  Jessica began to feel a bit more relaxed.  Becky noticed this so she pulled her to the dance floor and they started dancing.  

They danced for a while before getting separated.  Jessica tried to find Becky but saw her talking to some guy and began to feel a bit angry when they started kissing, so she went to the living room and sat on the couch with a beer.  Her head was spinning from all the beer and loud music and the heels were killing her feet.

"Mind if I join you?" a voice said.

She turned and saw a guy standing at the doorway.  He was 6'0", muscular, with short black hair and was smiling at Jessica.  Jessica recognized him from one of her lecture classes, and although they've never actually met, she hoped he didn't recognize her as Jesse.

"Uh, sure," she answered in a girlish voice, "I just needed a little quiet.  My friend dragged me here, but I'm not really into these kinds of parties."

"I know what you mean," the guy answered sitting down next to Jessica, "I'm not really into the parties, but this frat can help me land a good job after college.  My name's Kyle, by the way."

"Nice to meet you," Jessica replied, "I'm Jessica."

"Well, it's nice to meet you too," he said glancing over her body.

They sat for a while getting to know each other, when Kyle asked, "So does your boyfriend know you're here tonight?"

"I don't have one," Jessica answered unknowingly in a flirty tone, "do you have a girlfriend?"

"Well, as a matter of fact I don't," Kyle responded looking into Jessica's eyes.

Jessica began to feel confused.  She was sitting on a couch at a frat party flirting with a guy.  Kyle had moved closer to her and put his arm around her.  He placed his hand on her soft thigh and was gently stroking her smooth skin as their lips met.  She was still a boy, she thought to herself, and she wasn't gay.  She knew she had to stop this before it went too far.  

"Um, Kyle, I have to tell you something," she said stumbling over her words and after breaking the kiss and taking his hand off her thigh, "I'm really a guy.  My girlfriend dressed me up tonight to see what it's like being a girl because she was tired of me complaining all the time.  I'm sorry if I misled you, I'm not gay, and I hope you'll forgive me."

Kyle put a finger to Jessica's lips and said, "don't worry it's OK.  I'm not mad.  I actually understand, my girlfriend in high school did something similar on Halloween one year, and I really learned a lot from the experience.  I have to say though you make a really hot girl, a lot better than I did."

"You really think so?" Jessica answered blushing and smiling a little.

"Yeah, and it's up to you, but if you'd let me, I'd like to teach you a few more things about being a girl," he said.

Jessica sat in silence for a moment.  She knew what Kyle had in mind, but wasn't sure if she was ready to do this.  She was also still feeling a little angry at Becky for forcing her to come to a frat party dressed as a girl and making out with some other guy.  Then she thought to herself that she was a girl tonight and might as well get the full experience.  Besides it was only for one night and if Becky was going to have some fun tonight, then why shouldn't she.

"Um, OK," she replied smiling.

Kyle smiled back and put his hand on her chin then leaned in for another kiss.  Jessica felt weird at first, but decided to give in and opened her mouth.  Their tongues moved around each other's mouths as Kyle began to explore her body.  As they kissed, Jessica began to feel more comfortable and although she wasn't attracted to Kyle sexually, the feeling of being kissed and having her soft skin touched made her feel really sexy.  

Kyle stopped kissing her and took her hand and led her upstairs to a bedroom.  As they went in the room, she noticed two couples coming up the stairs behind them.  One of the guys was the guy Becky was kissing, but he was now with a different girl.  Kyle closed the door and locked it, then reached around and unzipped Jessica's dress letting it fall to the floor.  He led Jessica to the bed where they began making out again, this time more passionately.  

Jessica moaned in pleasure as Kyle began stroking her thighs and kissing her neck.  He reached down and took off her heels.  She wrapped her legs around him as they continued to kiss.

Kyle stood up and removed his clothes until he was only in his boxers.  Jessica stared up at him and was surprised to find she found Kyle pretty attractive.  She was feeling confused, but in the moment she didn't think of herself as a guy, but rather a sexy college girl.  She decided to really go for it and reached around and unhooked her bra then tossed it aside.  

She stood up and they began to kiss and Jessica reached down and began stroking Kyle's penis.  It soon became hard in her hand and she knelt down and pulled down Kyle's boxers.  She paused for a moment staring at the erect penis before her, then slowly kissed the tip, tasting the precum in her mouth.  She pulled back for a moment getting used to the taste of the precum in her mouth and decided that she might as well try it.  She licked her lips then slowly began to lick Kyle's penis while massaging his balls.  She looked up at Kyle who was clearly enjoying it and felt his penis grow harder.  She took the entire penis in her mouth as it continued to grow.  Kyle moaned and grabbed her head as she sucked him off and soon shot his load into her mouth.  She gagged a bit as she swallowed it.  She stared up at him licking her lips.  

"Wow that was incredible," Kyle said, "that was the best blow job I've ever had."

Jessica stood up and kissed him sharing his load.  She knew she might regret it later, but she decided she might as well get the full experience of being a girl as she would probably never do this after tonight.  She whispered in his ear, "I'm ready to go all the way."

She pulled her thong down her legs and stepped out of them as Kyle stared in disbelief.

"Like what you see?" she asked seductively as she put her hand on her hips and flashed him a sexy smile.

"Wow, you really went all out," he said as he admired how real her breasts and vagina looked.

He led her to the bed and laid her down.  They began making out again and Kyle kissed his way down her body, which made her feel really hot.  He soon got hard again and climbed on top of her and she wrapped her legs around him as he slowly stuck his penis into her pussy.  Jessica moaned in pleasure as Kyle shot his load into her.  

Kyle rolled off of her and they laid together in silence for a moment recovering from what they had just done.  Jessica rested her head on Kyle's chest as he held her close and stroked her hair.

"So, how was it?" Kyle asked.

"Incredible.  It felt so good experiencing sex as a girl, but I don't think I'll try it again," she said.

Kyle suggested they go another round and try anal, but Jessica felt uncomfortable going that far and declined.  They both laughed and shared another long kiss, then Jessica gathered her clothes and went to the bathroom to clean herself up and take a quick shower to wash out Kyle's juices.  She got dressed and touched up her makeup and fixed her hair.

"I had a wonderful time," she said stepping back into the room, "but I better find my girlfriend and get going."

They kissed one more time then Kyle took her back downstairs.  She wandered through the party and found Becky, who was playing beer pong.  

After winning the game Becky turned to her and said, "Ready to go?"

"Yeah," Jessica said, "I think I've had enough for one night."

As they left the party Jessica noticed Kyle in the crowd and gave him a small smile, but Becky was too drunk to notice.

As they walked back to the apartments, Becky asked, "So did you learn anything tonight?"

"Definitely, and thank you for that," she said, "tonight has definitely made me understand women better and probably made me a better boyfriend too.  You definitely won't hear any complaints from me anymore."

Becky smiled and said, "I'm glad to hear that, it sounds like you had a good time.  What did you do all night?"

"Oh, just hung out," Jessica answered smiling to herself.

When they got back to Becky's apartment Becky said, "well since you were such a good sport tonight, I'm gonna give you a little treat."

She handed Jessica a babydoll set and said, "I've always wanted to try being with a girl.  Put that on and let's have a little fun."

Becky smiled and pulled Jessica close and they began to kiss.  They broke the kiss and Jessica went to the bathroom to change into the nightie.  She came out and saw Becky dressed similar.  

They climbed into bed and began kissing passionately.  Soon they were both naked and exploring each other's bodies.  Jessica loved the feeling of their soft hairless skin and supple breasts rubbing against each other, a feeling she had never experienced as Jesse.  Jessica ate out Becky as Becky moaned in pleasure.  When they both climaxed they drifted off to sleep wrapped in each other's warm embrace. Jessica smiled as she remembered everything she had done that night.  Although she had enjoyed the experience with Kyle, she found she enjoyed being a lesbian alot more, and wondered if Becky did too.

The next morning they woke up and shared one last lesbian kiss.  They put on their nighties and had some breakfast then began transforming Jessica back into Jesse.  Becky removed Jesse's makeup and nail polish, then removed the breasts and vagina.  She untaped and untucked his penis.  He took a shower and stepped out looking into the mirror.  He was still hairless, but gone was the sexy girl from the night before.  He dried off and went back into the bedroom and changed back into his male attire.  He also asked Becky to cut his hair shorter as it still looked pretty feminine.  He watched as the last traces of Jessica disappeared, leaving only Jesse behind.

After they were done, Jesse packed his stuff, kissed Becky goodbye, and headed back to his apartment.  That night they got together to discuss what had happened the night before.  Becky told Jesse that she may be bisexual, but that she thinks she likes guys alot more.  Jesse told her he was fine with this and admitted that he enjoyed being Jessica and wouldn't mind dressing up again in private.  Becky agreed and told him he wouldn't force him to dress up again, but she would enjoy spending time with Jessica again should she choose to return.  That night they made love and Jesse and Becky, more passionately than they ever had before.  From that night on they felt alot closer and more connected as a couple.  

After that night he never dressed as Jessica in public or tried anything with a guy again, although he and Becky dressed as sexy schoolgirls on Halloween their senior year with some friends, who had decided it would be funny for the guys in their group to dress as girls that year, and luckily he wasn't recognized by anyone from that night.  A few of their friends, including some of the guys who were also dressed as girls, although not as convincingly, told him he made a hot girl and jokingly hit on him. A few even told them that if they didn't know better they would think he was a real girl and did a really good job for his first time dressing up.  If only they knew.  

He would occasionally see Kyle in class, but Kyle didn't recognize him as Jessica and they never talked.  In the days after that night he would look at Kyle and other guys a few times to see if he was attracted to him or men in general, but felt nothing and realized the attraction he felt as Jessica must have just been a rush of emotions from the excitement.  

Jesse also found he had in fact become a much better boyfriend and was also more patient and receptive to Becky, now knowing from experience how much preparation it takes women to get ready for a night out, how guys treat and hit on attractive women, and what turns a girl on during kissing, foreplay, and sex.  Becky often wondered how their lovemaking became so much longer and more passionate, but never asked.  He would occasionally dress up as Jessica, this time with a wig, for some lesbian sex with Becky, but they eventually stopped once his body hair grew back.  

They eventually got married after college and started a family.  In the years after college he never dressed as Jessica again, but he kept the ID card and some pictures as mementos and often looks back in fondness at the night, and few other experiences, he spent as a girl and the lessons he learned from the experience.  
A story of a young college guy spending a night with his girlfriend as a girl after she becomes frustrated with his difficulty understanding her. As with my other story, if you would like to draw images to accompany the story let me know. Looking for a good artist to make the story more fun.
:iconautisticmatt:
Autisticmatt Featured By Owner Oct 27, 2010
Wonderful! I would have loved to be Jessica that night, reading this i ahd to take matters into my hands! love Trisha
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:iconescafa:
Escafa Featured By Owner Sep 4, 2010  Hobbyist Traditional Artist
Your incredibly talented keep it up. :)
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