Ashleigh?

Story Info
First time feminized.
1.6k words
4.14
48.3k
10
1

Part 3 of the 3 part series

Updated 06/08/2023
Created 11/14/2017
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Ashleigh?

For the past week I have been obsessed with what happened between John and myself. I have not been able to think of much more than our sexual encounter in his car. I have not been able to concentrate in school and when at work I keep hoping to see him, but haven't so far.

When I arrived at work on Friday I found a bag in my locker with a note:

Wear this tonight after your shift and meet me at the back door after everyone has left. Your secret admirer.

I took the bag from the locker and peeked inside, I didn't want to take out what was inside with others around but I think it was some type of clothing.

I put the bag back in the locker and went out for my shift but could not think of anything other than what was in the bag in my locker and what was going to happen tonight.

As the store closed I cleaned up my area and closed down my register, I waited for everyone else to leave then went into the employee area and picked up the bag. I took it to the dressing area and opened the bag and pulled out what was inside. There were only two items, the first was a dress - a sexy black sleeveless short skirted dress. And the second was a tube of lipstick, very red. I stripped down to my underwear and wondered if I should leave the underwear on or take it off. I thought about it for a moment and went ahead and stripped down totally naked. I put the dress on, taking care to pull it down over my hips, if fit quite well. Most of the lights were out so the dressing room was dimly lit, I looked in the mirror to see myself in a dress, I had never been in girls clothes before and it felt odd but scintillating. In the mirror I could make out a thin girl with short hair, few curves and flat chested. I shook my hips to make the skirt shake and it wasn't long a bulge began to appear where it shouldn't for a girl.

Ii took the tube of lipstick and leaned in close to the mirror and applied it to my lips, the best I could. I stepped back to look at myself, with more work I might be able to pass for a girl I thought. It was getting late so I put my clothes into the bag and snuck out of the dressing area, making sure I didn't run into anyone by accident. I made my way to the back of the store.

The back of the store was darkened only lit by a few exit signs so it made it hard to make out where I was. "John" I whispered, "John are you here?"

"Yes, I am over here" he whispered back.

"Keep speaking so I can find you."

"OK" he answered. And he kept saying "Over here."

I worked my way towards his voice, eventually reaching him.

"What are we doing?" I asked him.

"I haven't been able to forget the other night and I wanted to see you again." he said.

I was so excited to hear that, I felt the same way. "But why the dress?" I asked.

"I'm not gay" he said "so I think it will be better for me if you are a girl."

I didn't know how to take that, I felt a little insulted as I wanted him as he was. I didn't know if I should let him know and walk away or stay, but my hormones got the best of me and I stayed.

"Come closer" he instructed. As I moved closer he took me by the waist with his hands and pulled me closer to him. John is a bit taller than me, I am about 5'7 and he is 5'11 or so. He then took my head and pressed it against his chest, I could feel his hard cock against my stomach.

"I am excited to feel you again" he said "I missed you."

"I missed you too" I replied as I reached down and gently rubbed a finger against the outline of his hard cock pressed into his pants. "Can I see more?" I asked.

"Of course" he replied.

I stepped back and took his tie in my hands, loosening the knot. Then I undid the buttons starting from the top and working my way down, pulling the shirt out of his pants to get to the last button. With his shirt undone I gently kissed his chest as I reached down to undo his belt, with the belt undone I unbuttoned the pants and lowered the zipper. With easy access I reached into his underwear and began playing with his cock. Stroking the shaft, rubbing the head with my palm, feeling the pre-cum as it lubricates his cock.

He moans with pleasure as I continue to stroke it, then I begin to kneel down in front of him and when I am on my knees I reach up and pull down his pants and underwear in one fell swoop. His boner pops free right in front of my face, I reach up and direct it to my mouth and begin licking it from base to tip. Over and over, along the under side of the shaft just kissing the very wet tip.

Then I take the base in one hand and press my lips against the head, slowly pressing further allowing it to penetrate me. I tilt my head directing the cock into my cheek, then backing it out and doing the same for the other side of my mouth. Spreading the feeling of his warm member to all areas of my mouth, tasting the salty pre-cum. Eventually I allow his cock to tickle my throat, as it moves along the roof of my mouth to press against my throat. I feel him grab my head forcing it in further in short motions, eventually my nose presses into his stomach and his hairy balls press against my chin, he is all in.

"Oh Ashleigh, you are so good at this" he says softly "I love how you make me feel."

It took me a moment to register what he had said, but who is Ashleigh? Is that me, a girl he wants to fuck, or an ex-girlfriend of his? I was not sure, and with my mouth full I could not ask him, but I looked up at him to try and make eye contact. I looked and he had his eyes closed, face towards the ceiling, moaning with pleasure.

The blowjob continues for quite a while but eventually I feel his cock harden further, his balls tighten and with one large gasp he lets the first shot of cum go into my mouth. It surprises me as it hits the back of my throat and makes me gag, I pull back and his cock pops out of my mouth. He continues to shoot cum and it starts to hit me across the face, I desperately try to get his cock back in my mouth and he grabs the back of my head to help guide me. I do get it back in my mouth after two or three cum shots hit me across the face. I take the rest of his orgasm in my mouth and allow the cum to fill it.

I am not sure if he can see me, but I must look a mess with cum over my face, in my hair and running down my cheeks. I can feel the warmth of each shot across my face, I use a finger to try and direct the flow of each ejaculation into my mouth. As I do he asks "did you swallow?"

I mumble, "not yet."

He rubs the head of his softening cock against my lips, then reaches down to cover my throat with his hand. "Go ahead and do it now."

I use my tongue to move his cum so that I can swallow it, he moans as he feels my throat contract to take his cum.

Then he begins to re-button his shirt, when he is done he reaches down and pulls up his underwear then pants. Getting himself back together before heading out.

"Do you have a ride home?" he asks.

"No" I reply "I was hoping you could drive me home."

"OK" lets go.

"Should I change first?" I ask.

"I don't have time, you will have to change in the car."

So we walk out the back door and he locks things up. We get into his car and head home to my dorm. While he drives I pull my clothes out of the bag and try to slip them on, underwear first, socks and then pants. With my pants on I pull off the dress and on my shirt. Lastly I put on my shoes and clean up the dress placing it back into the bag. When we reach the curb outside my dorm I get out and before closing the door I say "thank you."

I try to sneak into the dorm so nobody sees me, I head into the bathroom and notice the lipstick. I remove the lipstick with a paper towel and then use it to clean any cum remaining in my hair and head back to my room. I stick the bag with the dress and lipstick in the back of my wardrobe so nobody finds it.

Ashleigh Swift

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
1 Comments
Brian70Brian70over 6 years ago
Great Stories!

So hot, I love the encounters. I can't wait to know where this goes. Thanks!

Xoxo

Share this Story

READ MORE OF THIS SERIES

Ashleigh Series Info

Similar Stories

Dressed up for Halloween A costume decision ends up with sex.in Transgender & Crossdressers
My Feminine Side Guy becomes a beautiful sexy girl.in Transgender & Crossdressers
Perfect Little Slut CD's fantasy comes true with the help of a trusted friend.in Transgender & Crossdressers
The Guy in My Wife's Panties Hotwife turns hubby into crossdressing faggot.in Transgender & Crossdressers
Hypnotized at the Costume Party Brad is turned in Brandie.in Transgender & Crossdressers
More Stories