tagTransgender & CrossdressersAshley's New Friends

Ashley's New Friends


All characters in this story are over 18 years old. This is a work of fiction and any similarity to other works or real people is simply coincidental. Special thanks to my best friend for editing this! Hope you enjoy, love you dolls! Xoxo


One day Asher was sitting in a library on campus doing his homework, or at least he was supposed to be doing his homework. Instead he was daydreaming about dressing up as a girl and going to a frat party next week after the football game.

Suddenly a tall woman with extraordinarily large breasts walked up from behind him and gently whispered in his ear "Sweetie you might want to pull your pants up some in the back, everyone can see your pink panties."

Asher turned pale as a ghost. He always lived in fear of people finding out about his fetish. Even though it was starting to get warm outside he wore a jacket today just to avoid this situation, but apparently his jacket twisted when he sat down revealing his girly underpants to the world.

"Oh honey, it's ok, don't worry about it. I used to have an ex who was trans and I used to help him with clothes and makeup all the time, you're safe with me."

Asher embarrassedly said his thanks and then hurriedly left the library.

The next day while walking to class he noticed the same girl talking with her friends and waved. To his shock she walked over to him and said "Hi I didn't get a chance to formally introduce myself yesterday, my name's Daisy. And you are?"

"Asher." He answered.

"Oh that's such a pretty name! Ok I'm just gonna cut to the chase, here's my number, text me later ok?" And Daisy gave Asher a slip of paper with her phone number on it.

Asher stumbled over his words and thanked her as she walked back to her friends.

That afternoon lying in his bed in his dorm Asher decided to text Daisy.

He sent her a simple "Hi".

She responded with "Hayy. Ok so listen. If you don't have plans Friday night, would you wanna come over and do makeup? Maybe even bring a couple outfits."

Asher's heart leapt out of his chest. He had wanted this for so long. A genetic girl friend who accepted him and even wanted to help him! It was a miracle!

Asher quickly typed out "YES! I'd love to do that! I'll see you Friday, 7:00?"

"Sounds good to me! See you then sweet stuff! "

Since today was Thursday Asher only had to make it another twenty four hours.

He could barely focus in class the next day, all he could think about was his plans for the evening.

Finally the time came. Daisy had sent him her building and room number, so he packed up the meager makeup he had as well as one of his favorite outfits; lacy white bra, matching thong, and a cute little black dress.

He made his way over to her dorm and politely knocked on the door.

"Come here!" Ashley said excitedly and brought Asher into a tight hug.

She was wearing a tight tank top that was always threatening to expose her ample breasts and short shorts that showed of her beautiful legs and thick thighs.

"Ok go ahead and go into the bathroom and change. I already have all my makeup laid out and ready." Daisy said excitedly.

Asher did as he was told and went to change his clothes. When he came out Daisy was texting someone on her phone.

"Ok come here and sit down." Daisy said and Asher followed.

"Ok, the first thing that we're gonna do is put on some primer. This is also gonna moisturize your face so your makeup doesn't dry your skin out."

Daisy squirted some of the primer into her hand and started to rub it on Asher's face. It was the most wonderfully relaxing thing that he had ever felt. It was like getting a facial massage using some sort of relaxing drug.

About 15 minutes later they were done. Daisy had very gentle hands and it felt wonderful to have her do his makeup. He was hard as a rock, fortunately his thong mostly hid his erection.

After the makeup Daisy did his hair. She drew his longish hair into two simple pigtails and tied them with pink bows.

Finally Daisy held up a mirror for Asher to look at himself and when he looked all he saw was a gorgeous girl looking back at him.


"Now all you need is a girl name. How about Ashley?" Daisy questioned.

"I love it!" Asher, now Ashley, said and went in for a big hug. She could feel Daisy's large, squishy breasts against her body.

"I'm so happy you like it! Now, what else do you wanna do for girls night?"

Asher was too scared to leave the dorm and go somewhere so eventually they decided to watch a movie. They decided on a classic chick flick. After a while Asher got cold and started to shiver a little.

"Oh honey, you're cold, let me go get a blanket."

Daisy went and brought Ashley a blanket and then they curled up on the couch together. Ashley rested her head on Daisy's breasts and felt so content.

After a while the lock on the door jiggled and the knob started to turn. Ashley jumped up in fear of who might be coming in.

When the door opened a large black man came through the door and said "Hey babe, in done with practice for the night. Hey you must be the new girl."

Daisy looked over at Ashley's expression of confusion and horror.

"Ashley this is my boyfriend Tyrone, I'm sure you recognize him from the football team."

Once she pointed it out Ashley did realize who it was. Tyrone Jackson, the star quarterback for their college and apparently Daisy's boyfriend.

"Ok babe, I'm gonna go take a shower." Tyrone said to Daisy.

"Ok babe, we'll be ready when you get out." Daisy replied. Tyrone went in for a deep kiss and grabbed one of Daisy's huge tits in one of his giant meaty hands. After a few moments he pulled out of the kiss and slapped Daisy's tit and stuck his finger in her mouth for a moment then headed off to the bathroom.

"Ok it's time to get you ready." Daisy said. Ashley was scared but shook her head.

"Come here and bend over my lap." Ashley complied. Daisy's legs were squishy and he could feel her breasts on his back.

"Ok have you ever had anything in your ass before?" Daisy asked as she began to rub her hands on Ashley's butt and back.

"Maybe a finger or two one time."

"Well what we're gonna put in there is a lot bigger than a finger. It's all gonna be alright though ok sweetie. Don't be nervous or it's gonna hurt. Just relax."

"Ok." Ashley replied as she felt butterflies in her stomach.

Daisy opened a drawer on the end table and pulled out a bottle of lube.

"Ok, I'm gonna put some of this on my finger and on your asshole and just start massaging the outside with my finger." Daisy explained.

Ashley could feel the cold lube hit her butthole as Daisy squeezed the bottle. Daisy then put some on her finger and started rubbing it in little circles on Ashley's hole.

At first it was uncomfortable but eventually Ashley started to feel good.

"Good job! You're opening up wonderfully! Now I think you're loose enough for my finger. Just push out like you're trying to poop and I'll keep going in circles. You'll feel a little pop when my finger goes inside." Daisy explained.

Ashley was still nervous about all of this but trying her best to stay calm, it was feeling pretty good however. And sure enough pretty soon Ashley felt a little pop as Daisy's finger slipped into her ass.

"I'm just gonna leave my finger here for a minute so you can get used to it. It might help if you clench your asshole a little for a few seconds every once in a while." Daisy said obviously experienced in this.

Eventually Daisy loosened Ashley's ass up enough to get 3 fingers in.

"That should be about enough. That's how much I have to loosen my ass for Ty." Daisy stated.

"He's ready for you babe!" Daisy called.

"Be there in a second!" Tyrone called back in his deep voice.

"While we're waiting on him I'll give you a little treat for being such a good little slut." Daisy said and started rubbing Ashley's prostate. It was the most pleasurable thing she had ever felt in her life. It blew every orgasm he had ever had clear out of the water and she moaned like a true slut.

"Seems like somebody likes to have their p-spot played with. Maybe you can even have a sissygasm! I love it when that happens." Daisy said.

At that moment Tyrone came out of the bathroom.

He had the largest cock Ashley had ever seen. It was at least 9 inches long and 3 inches thick. There was no way it was gonna fit in her.

"Is the slut ready for me?" He asked.

"Sure is baby." Daisy responded with a purr in her voice.

"Good job baby." Tyrone said and leaned in for a very deep wet kiss with loads of tongue.

"You ready to get fucked slut? I hope so." Tyrone said menacingly.

All Ashley could do is whimper.

Daisy moved around so that Ashley was laying on top of her with his heads on her breasts.

"Since this is your first time I'll let you lay here so that I can help you get through it." Daisy explained.

"Okay." Ashley managed to squeak out weakly.

"Get ready slut." Tyrone said.

Ashley felt his cock at her back door. He felt her start to push. Ashley moaned uncomfortably.

"Damn slut, you tight!" Tyrone said excitedly with a laugh.

Suddenly there was a popping sensation as the head of Tyrone's cock slipped into her ass. It was the most painful thing Ashley had ever felt in her life and she screamed loudly.

"Ok slut, it's gonna be alright, daddy Tyrone might be a mean motherfucker, but he wants his slits to enjoy it as well." Tyrone said in a surprisingly soothing voice.

Daisy held Ashley's head to her breast and whispered "Shh, it'll be ok honey, it'll be ok." into Ashley's ear.

The three of them stayed like that for a time while Ashley cried into Daisy's breasts.

Eventually Tyrone said "Ok slut, it should be alright now, I'm gonna start moving, I'll be gentle though."

Ashley begged and pleaded for him not to but he did anyways.

Ashley moaned in pain and pleasure as Tyrone started to push his enormous cock deeper.

After a few minutes the pain subsided and it started to feel a little good, then Ashley started moaning for a different reason. Tyrone's cock hitting Ashley's prostate was the most amazing thing she had ever felt.

As Ashley got fucked Daisy started to get turned on too. She pulled her enormous breasts out of her skimpy tank top and held her nipple out for Ashley to suck.

Ashley latched on like a hungry babe suckling her mother's teet while grabbing the other breast with the nipple between her fingers.

The trio went on like this for a while until Ashley and Daisy's moans started to get louder and Tyrone's thrusts and grunts started to get deeper and faster and all 3 climaxed at the same time.

As Tyrone's cock exploded in Ashley her cock exploded all over the front of Daisy's shorts and shirt while her ass spasmed on the giant hunk of man meat in her ass.

When Tyrone pulled out Ashley could feel the cold air hitting the inside of her gaping asshole and shivered while being incredibly turned on.

When the three calmed down Ashley and Daisy went into a deep wet kiss and held it for a moment until Tyrone pulled Ashley off of Daisy and threw her to the floor.

"Now, you didn't think I was gonna forget my baby now did you?" Tyrone said as he kissed Daisy and while she was distracted slid his cock into her pussy.

Daisy moaned in ecstasy and Tyrone's cock pumped in and out of her vigorously.

Ashley couldn't control herself and started stroking herself towards another orgasm. This time she started fingering her still gaping ass.

About 20 minutes later the trio once again orgasmed in unison. Ashley came so hard her cum hit her in the face and Tyrone's load was so big it spilled out of Daisy's well used cunt.

By the time they came Ashley had gotten her whole hand inside her already stretched ass and was self

"Wow that was one of the best fuckings I've given in a while. I need to go rest after that one." Tyrone said breathing heavily as he started to get dressed.

Before he left he brought his half hard cock back around for Ashley and Daisy to kiss it one last time.

When they kissed it they could taste the last little bit of cum, sweat, and pussy juice on the tip of his cock. Ashley decided that she had never tasted something so wonderful. Then Tyrone left.

"Welp it looks like it's just you and me now Ash." Daisy said looking over at Ashley. "How about you help me clean up." And with those words Daisy turned and spread her legs wide indicating the sissy's next task.

Ashley was instantly hard again and she crawled over and savored Daisy's well used cunt for a minute.

It was still wet and dripping with Tyrone's cum.

You could smell sex resonating from her pussy. It was intoxicating.

Ashley stuck out her tongue and gently licked the outside and got a nice big blob of cum on her tongue.

With the first lick Daisy moaned loudly and Ashley could feel her muscles surrounding her pussy spasm.

After the first lick Ashley went up for a deep wet kiss so that Daisy could taste the delicious mix of her own juices and cum. They held the kiss for a long moment with their tongues exploring each other's mouths.

Then Ashley broke the kiss and the pair stared into each other's eyes then Ashley dropped back to her knees and continued eating.

Daisy moaned lewdly and grabbed Ashely's pigtails while Ashley ate her.

After about 15 minutes Daisy's moaning intensified and Ashley could feel her muscles spasm as Daisy squirted all over her face.

Ashley was so turned on by this that she squirted her own load without even touching herself. The two then laid there in a mess of each other's juices and cum.

"Well, we should probably get cleaned up." Daisy stated and Ashley agreed.

"Maybe we can share a shower and then it's kinda late so you might as well stay here tonight...cutie." Daisy said as she got up and winked and then headed off to the shower.

The end

Report Story

byLucyAnn51© 6 comments/ 27990 views/ 20 favorites

Share the love

Tags For This Story

Report a Bug

1 Pages:1

Please Rate This Submission:

Please Rate This Submission:

  • 1
  • 2
  • 3
  • 4
  • 5
Please wait
Favorite Author Favorite Story

heartjuliahoutx, cali3nt3s and 18 other people favorited this story! 

by Anonymous

If the above comment contains any ads, links, or breaks Literotica rules, please report it.

There are no recent comments (6 older comments) - Click here to add a comment to this story or Show more comments or Read All User Comments (6)

Add a

Post a public comment on this submission (click here to send private anonymous feedback to the author instead).

Post comment as (click to select):

Refresh ImageYou may also listen to a recording of the characters.

Preview comment

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: