(Some of this story may be slightly fabricated, but don't worry about what is and what isn't, just enjoy the story.)
It was back in February when me and my girlfriend plus a few friends decided to go to a con. We hung out together and thought it would be fun. A friend bought my ticket and the closer it got to the con, the more we were excited.
Not only did we get more excited, the closer we got, the more my girlfriend begged me to cross dress.
"No. N-O. That's final."
"Why not?" She asked.
"Because I'm straight and don't want to be raped in the bathroom."
"You won't! I promise!"
"What are you going to do? Hold my hand while I pee?"
That usually ended the conversation.
As the con got closer we all decided to cos-play, but we weren't sure what as. Then it hit us we were living representations of the Scooby-doo gang! Minus Scooby doo of course. I was to cosplay as Shaggy, my girlfriend as Velma, my best friend as Fred and my other friend as Dahpne. We even got an old van painted like the Mystery Machine to tie it all together.
When we got to the con plenty of people asked for pictures, we were so proud.
There were plenty of cross dressers there, mostly 30 or 40 year old men that didn't even look like a woman. I would count how many I saw, so I could tease my girlfriend. Once I got to 46.
"Please?" She said when we had stopped for lunch.
"What?" I was confused.
"Cross dress for me?" She batted her eye lashes and gave me... well you know... that face.
"Mmmm..." It was hard to resist looking straight at her, "Sure," I gave in.
"YES!" She gave a little dance.
My cheeks turned red as I thought of how stupid this would be. I gave a fake smile to her as I started to think of all the people I knew at the con, and how many could take pictures.
The next morning I got up early so I could get to my girlfriends house to get redressed, I'm sure my parents wouldn't have appreciated the "new" outfit.
I got to her house and she threw me a plastic bag from the couch.
"You're not even going to tell me how to put this stuff on?"
She sighed, "I guess I'll have to..."
I took off my clothes until I was completely naked. She tossed my a pair of her panties, they had roses all over them. I gladly put them on, that was the only part of this I would enjoy.
I had purposely not shaven anything so I wouldn't get into the role of being a woman, this was just a one time thing just to make my girlfriend happy. She frowned at my extremely hairy legs.
"I don't mind the face, but why couldn't you have at least shave THOSE monsters?"
I shrugged and put on some black leggings. They conformed to my legs, feeling very smooth and fresh. Next the dress. It was a blue floral dress. Very open and free. Then a grey cardigan.
She frowned and looked at it on me "I didn't realize how good that dress and cardigan go together!" She clapped her hands.
I rolled my eyes. "Yeah whatever."
I put on some Converse sneakers and she helped put on a blonde wig. It felt different having hair laying across my shoulders.
"Fuck!" I thought to myself, "What did I get myself into?"
To complete the outfit she put a mood necklace around my neck.
She jumped up and down and clapped her hands. "You look sooooo good! Oh! I almost forgot! We need a name for your inner cross dresser..."
"Uhhh... no... this is enough, thank you."
"No!" She laughed, "Hmmm... how about Marget?"
"NO!" I shouted.
"You like it? Good. That's your name for the day, big girl."
I sighed and blew a hair out of my face.
"Fred" pulled up in her driveway and I grabbed my purse that was preloaded by yours truly. I walked out side, opened the passengers seat door and sat down.
"Well hello who are... AHHHHHH!!!" He screamed as he turned and looked at me.
"Not another fucking word." I restrained the massive urge to punch him.
"But you... your ass was... gahhh!" He sat back in the seat red-faced.
My girlfriend came and sat in another seat behind him. "Hey Fred, I see you've met Marget."
"Fuck you!" We both said at the same time.
As I walked through the con I did get a couple of strange looks and a couple of winks. But the weirdest thing happened in the bathroom.
I went to go pee, and there was a big man in there, he winked at me, and I decided I could wait to go, and washed my hands. He walked over to a stall and pointed inside and winked again.
I got out of there as fast as I could.
The only thing that stopped me from stripping down and leaving was that I was wearing my girlfriends panties and I didn't have a change of clothes.
As the day was wrapping up we (we being me and my girlfriend) went back to the Mystery Machine and sat in there and talked.
"Was it fun?" She asked
"Only because I'm wearing your panties."
"Do it again next year?"
"Why not?" She gave me a pouty face.
"Because it's embarrassing," I whined.
She rubbed my chest as we lay down in the back. "Poor baby," she said sarcastically.
I stuck my tongue out at her. She gave me a sexy look and said "Put that tongue where it belongs."
I gave her a confused look, then she pulled off her pants, next her panties.
I looked at her beautiful pussy, I had seen it before but it looked especially good today. I started to reach out and touch it, but she playfully slapped my hand away.
"No no, you're only allowed to use your tongue." She winked.
I shivered and went in, I had never attempted this before and was excited. As my tongue touched her wet pussy she whimpered and cringed. I licked it up and down, feeling her body shiver as I brushed over her clit. I reached up under her bra and gently twisted her nipple, she moaned and curled and uncurled her body.
She reached over and brushed my cheek and told me not to stop, and pulled my waist toward her face. She pulled down the leggings and panties in one motion and looked at my cock, I personally thought it was small, but she kept saying it was huge, whatever floats your boat.
She took the whole cock and shoved it in her mouth, it felt great as her head went up and down, I showed her how much I liked it by returning the favor I pinched her nipple harder and licked the pussy even more passionately.
The more I sucked her pussy, the better she sucked my cock, the better she sucked my cock, the more I sucked her pussy.
The endless cycle of ecstasy continued until she shouted, "Oh my god! I'm cumming! I'm cumming!"
She curled up and sucked my hard cock so much that I could feel myself cumming as well. We both came at the same time and she let out a sigh of relief as we lay down next to each other, pulled our clothes back on and we held each other until Fred and Daphne came to the van and drove us home.
All together, it was a great day.
This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than Lushstories.com
with this note attached, it has been posted without my permission.
<a href="https://www.lushstories.com/stories/crossdressing/how-to-please-your-girlfriend.aspx">How to please your girlfriend</a>