Getting Caught Isn't Always So Bad

Story Info
Evan gets caught by his best friend.
2.2k words
4.52
171.2k
79
5

Part 1 of the 2 part series

Updated 09/22/2022
Created 04/21/2008
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
dani_boi
dani_boi
164 Followers

It is Saturday night and I'm getting ready to head to a local club. I begin by taking a nice long hot bath and shaving my bodies nice and smooth. Well except for a sexy little landing strip. My lean body looks so good all shaved smooth. My belly and nipple rings add to my excitement. Once complete I towel off my 5'6" 130 pound frame and begin to do my make up. My cock is starting to get hard as I check myself out in the mirror.

I guess I should explain I'm a bisexual cross dresser. Nothing feels better to me than that of silk, lace or other feminine things against my body. Add to that the feel of a hard cock in my mouth or ass and I'm in absolute heaven. I have been dressing "in the closet" so to speak since I was young. No one knows of my secret and I go to great lengths to keep it that way. Like every time I go out I make sure to leave at night and keep my car parked in the garage. This plan was working for me very well or so I thought.

After finishing my makeup and styling my blonde hair into a funky sexy do I begin to dress. I have a very extensive collection so this part takes great consideration. I decide tonight I want to be extremely feminine. I first start with some white thigh high stockings with a seam up the back. Next comes pink boy shorts, it takes a moment but I get my semi hard cock stuffed into the panties. Then I slide on a pink garter skirt and attach the stockings. I check myself in the mirror and feel very sexy. Next comes my pink corset. I love the way it gives me sexy curves and the feel of the satin is incredible. I get it tied really tight and once again stop and look in the mirror. A sexy blonde hair blue eyed woman stands before me. I give a slow turn and check out my firm sexy ass. Many a woman has been envious of it. I reach to the hanger and take my Pink leather dress; I step into it and feel how it hugs my every curve. With a little work I get it zipped up and run my hands over my body. Next I put on my dangling earrings with pink stones. God I love pink! As if you could not tell. I slip into my white ankle strap patent leather pumps and buckle the straps. The four-inch heels tighten up my calves and ass. Finally I place on each ankle and wrist some pink leather cuffs with D rings and my Pink collar with pink stones. I attach a leash to it and am ready to go.

The club I am heading to have a B&D theme but it is more of a light atmosphere than anything hard-core. You get anyone from the lookers all dressed normal to those who go all out like me. I grab my purse and head down stairs, grab my keys and I'm off to the... I stop frozen in my tracks. My best friend is standing in my living room looking back at me. Now let me tell you I am very passable and under normal circumstances nobody who knows me would even think this was me. But like I said "normal" circumstances. Here I am in my house in front of a guy who has known me for 20 years since grade school and who has seen me dress as a girl for Halloween. So it is clear he recognizes me right away.

"Evan what the fuck is going on", breaks the silence?

"I thought we were watching the game tonight?"

"I um don't know what to say Mark, Jesus this is so embarrassing!"

"Ah you think so? How long have you been dressing like this?"

"For a long time."

Mark walks over to me, as I stand frozen. He is looking me up and down as if sizing me up. Mark is a lot bigger than me. Typical Jock in high school he is 6'2" 220 and as I have to admit very sexy. I have always had a crush on him, but never ever acted on it as my friendship meant more to me than anything else.

"I must say Evan you make a very hot chick, I mean really smoking hot. Ya know when you dressed up in high school I thought you were a fox then too."

I felt my cheeks begin to blush as my best friend was checking me out and paying me compliments. My thoughts immediately went to thinking about sucking on that gorgeous cock of his. I tried to control myself and just stood still.

"So where were you heading to in such a rush" Mark says as he comes back around in front of me again.

"To a club downtown" I reply.

"Well we had a date to watch the game so why don't you get that hot little ass in the kitchen and get me a beer and something for yourself."

I quickly turn into the kitchen and get Mark his beer and a glass of wine for me. I drink the first one down while standing in the kitchen. My mind is racing as to what is happening. I pour my second glass and bring them in handing Mark his and then trying to move over to the other sofa. He grabs my arm and pulls me down next to him.

"Where are you going Evan? Wait this is all wrong, if you are going to be dressed all sexy we can't be calling you Evan. What is your girl name?"

Horrified I hear myself blurt it out quickly "Katie."

"Mm that is a sexy name Katie, it is very nice to meet you."

I look at him puzzled "Serious Mark what is your plan because I'm feeling like a fool here and you are just acting like nothing abnormal is going on? Are you going to tell people, beat me up, what? It is driving me crazy!"

Mark looks into my eyes with the most sincerity I have ever seen from him. "Look Katie, I would never ever beat you up, tell anyone or anything else you didn't want to do. You are my best friend and I was just having a bit if fun. I really do think you are hot and am very turned on by you right now. You have no reason to feel like a fool. If anyone should it is me that is the fool. I've never had thoughts like this before but I just feel so turned on right now. I want you so bad but don't want to hurt you by making you do something you don't want to do."

With that and without thinking I moved in and pressed my lips to him. After fantasizing about him for so long I was actually kissing my best friend. He quickly took over the kiss and pressed his tongue into my wanting mouth. My hands touched his face as his roamed my body. Electricity coursed through my veins as lust took over and I climbed into his lap. He continued to explore my body with his hands as I broke the kiss and began licking his neck. God he smelled so good as my tongue licked and mouth sucked on his neck before going back up and pressing to his mouth. Heavy breathing and moaning was all that I heard as I felt his cock begin to harden under my ass. My leather dress was riding up and Mark had his hands on my thigh highs. I began to grind into his cock meeting his thrusts. Mark's hands moved up my chest and began rubbing my sensitive nipples.

"I want to suck your cock so bad" I breathed into his ear.

With that he picked me up and set me on my feet. He stood up and stripped and I got my first look at his chiseled body since we played football together in high school. My hands pressed to his chest as he found the zipper of my dress. Pulling it down he freed me of my dress and let it fall to the floor.

"Wow" was all he could muster to say.

Mark's cock stood straight out and was absolutely gorgeous. I knew right then that I had to have it in my ass as well. Mark grabbed the leash and pulled me to my knees with it. He continued to hold it as he pulled me to his cock. I moved my head in closer and took his cock in my hands. My painted nails contrasting his skin. Here I was my best friends cock in my hands, dressed like a slut and loving it more than any other time. I have had many cocks in my hands, mouth and ass. But I knew this was going to be the best.

His cut cock was beautiful, about seven inches long and not too thick. He had a nice big mushroom head that I could not wait to feel in my mouth. I looked up into his eyes as I pressed my lips to it. My tongue slid out and licked the underside and Mark let out a low lustful moan. I licked all around the head getting it nice and wet then I pushed it into my mouth and began working my tongue on the underside as I pulled it in and out of my mouth. I was getting very excited as I looked up and Mark with his eyes closed continued to moan but held that leash tight in his hands. My hand slid down the shaft and to his balls. I was happy to see he was not hairy down there as my head continued to bob up and down on his rock hard cock. I massaged his balls and had a very good rhythm going.

"Do you like my cock baby"? I heard Mark ask.

A muffled "Mmmhmm" was all I could get out with his cock in my mouth.

"Well my cock looks very good in your mouth."

I felt him begin to tense and I did not want this over yet, so I pulled his cock from my mouth and looked up at him.

"You can't cum yet stud, I need your cock in my ass. I want to feel you cum inside of me."

I couldn't believe what I was hearing, up till tonight I have always used condoms but now I just wanted to feel him, and only him inside of me. Shooting his hot seed deep into me. Marks eyes got really big and a huge smile came across his mouth.

"Really, Oh my god that is hot."

I knew from our many sex talks of how much Mark wanted to try anal with a girl but could never find the right one. Well he did tonight.

I reached for my purse and pulled out a bottle of lube. I gave it to him and told him to take care of me. I got up on all fours on the sofa and arch my back so my tight ass was in the air for him. Mark steps behind me and pulled my panties to the side. I could feel his hand begin to work the lube into my crack. Then a finger pushes in. I push back as electricity flows through me.

"Oh MY GOD" I moaned out.

Mark begins to finger fuck me with a nice pace. Then he adds a second finger and finally a third.

"I can't take it any more please put that cock in me and fuck me proper."

Mark takes the lube and rubs it on his cock. He then steps in behind me and presses it to my tight hole. He begins to push in as I push back to meet him. The head pops in and he stops for a moment. We both let out a low moan, holding my hips Mark begins to push in further. I feel his cock pulsing as it inches inside of me. Finally he is as far as he can go. I continue to moan as he pulls back out. I feel him grab the leash and pull back on it causing my back to arch in a sexy bow. He begins to fuck me at an increased pace, one hand on the leash the other on my corseted body. He licks and bites my neck as I push back with my ass to meet his thrusts. Suddenly I begin to spasm as cum begins to shoot into my panties. My orgasm causes my body to tighten which is too much for Mark. He begins to cum himself. Shooting his hot jizz into my wanting ass. I feel him, spurt after spurt as my own orgasm subsides. He holds my hips tight now and lets out one last moan before collapsing on me. I look back and he kisses me hard on the lips. His cock still buried deep in my ass.

"That was so fucking hot," I tell him.

Mark just smiles at me before kissing me again...

To be continued.

dani_boi
dani_boi
164 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
5 Comments
AnonymousAnonymousalmost 16 years ago
Yummy

Can't wait to hear more! I would love to have a sexy girl like you!

orvette1orvette1almost 16 years ago
WOW!!!

Your stories are so hot! This is a great one also!

TammiBadgerTammiBadgeralmost 16 years ago
I love sluts

I hope they make it to the club sometime. Maybe Katie can wear some pink boots. Will she be forced to service friends? Who knows? Just have fun.

AnonymousAnonymousalmost 16 years ago
Hot Story

Loved it

AnonymousAnonymousalmost 16 years ago
OMG GIRL!!!

I love your story, it's every closet dresser's dream, a steady boyfriend. Oh Katie wasn't it sooo wonderful when he filled you with his cum!!! Gawd I love the feeling!!

Share this Story

Similar Stories

The Babysitter Babysitter guy becomes babysitter girl.in Transgender & Crossdressers
My Sister's Boyfriend's Slut On my knees, my panties pulled down, for the first time in Transgender & Crossdressers
Maid The Wrong Bet... A French maid's outfit turns him into a sissy.in Transgender & Crossdressers
Changing Room Prank Mark and Greg help me discover myself with a harmless prank.in Transgender & Crossdressers
Left Alone Tommy plays dress-up and gets caught by his neighbor.in Transgender & Crossdressers
More Stories