Meeting Mario

Story Info
Kris hooks up with hot guy, who holds a spell over him.
4.5k words
4.5
1.9k
4
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

It was an early spring Friday night. I finally had some time to myself. I was sitting in my home office dressed in a black blouse, a red leather skirt, black pantyhose, red panties a black shaper and red strappy heels.

I was on my computer looking at women's clothes, when my phone vibrated. My Grindr app had a message. I had posted a picture of myself without my face on there. It had been a while since I hooked up with anyone, and tonight I had time to meet someone.

I opened my message and it was from "ItalianTop". The profile picture was a ripped torso. The message read "Hello there I am Mario, you have incredible legs."

I replied "Thank you, I call myself Kris. Great body if that is yours."

Mario replied "It is mine, thank you."

Mario continued the conversation, and it was like a date, as opposed to some of the messages you get on hookup sites like "host, suck me?"

We conversed for nearly an hour on messenger, He asked questions about my past, when I dressed etc, and I asked him about his experiences, what he was looking for etc.

I was horny at being courted like a date, even if it was via messenger. Mario finally asked me "Would you like to meet tonight?"

I quickly replied "Yes, I would."

Mario replied "My roommate leaves for work in about a 1/2 hour, unless I can come there?"

Meeting people as a closet Crossdresser is one of the more nerve-racking decisions you make. You worry about being outed, or meeting a stalker, or meeting someone you know. Going to their place the first time is very nerve-racking as well, you don't know if they are going to have unexpected guests, not answer etc.

The conversation I had with Mario lowered my guard. I replied back, "You can come here, here is my address"

Mario replied "I will be there in 20 minutes."

I decided to put on a little make up and my wig and nervously waited. I took a shot of Vodka to calm my nerves, I poured myself another one and the doorbell rang.

I nearly tripped with my heels on as I walked to the door, I looked through the peephole and it looked like a young Italian guy.

I opened the door and Mario walked in. He looked at me and said "Oh wow, you look hot!" I blushed and said so do you. He took his shoes off and I brought him to the living room. He sat on the couch and smiled.

I looked at him and asked him if he wanted a drink.

Mario nodded and I brought him out a Vodka and Sprite. Mario rubbed my pantyhose covered leg when brought it to him and told me to sit next to him.

I sat next to him and his hand moved to my thigh. He complimented me on my legs, and even how my toes were painted red. He continued to rub my thigh and then asked me "Would you rub my shoulders please?"

I nodded and he shifted on the couch. I maneuvered behind him and he took his shirt off. I was kneeling behind him, Mario turned around and said "Wrap your legs around me, I can rub them while you massage me."

I moved and soon my legs were spread wide, Mario caressed my nylon covered calves, thighs and feet. I massaged his neck and back.

He pulled away and got up. I didn't know what to do. He grabbed my hand and pulled me up. He put my hand on his rock hard cock through his pants.

Mario whispered in my ear "Kneel down and unbutton my pants Kris. It's time for you to be the sissy you are."

I got on my knees and reached up and unbuttoned his pants. I slid them down and slid down his underwear. A rock hard 6 inch cock popped out. I reached up and began to stroke it.

Mario looked down and smiled. "You are an eager slut aren't you Kris".

I nodded and he moved his cock to my mouth, I began to suck Mario's cock.

I licked the underside, and locked his balls, his whole groin area was shaved.

Mario moaned as I worked his cock. He talked dirty to me, calling me a "Whore and slut".

This got me going even more, and pretty soon Mario tensed, the initial blast of cum in my mouth was huge and I swallowed almost all of it. Some leaked out the corner of my mouth, but I kept up with the rest. I kept some in my mouth and when Mario pulled his cock out of my mouth I showed it to him.

He pulled away and sat on the couch, I got up and walked to the bathroom. I swallowed his cum, and gargled some mouthwash. I walked back into the living room, assuming Mario would be dressed and ready to go. To my surprise, he was still on the couch, naked. His cock was still 3/4 hard. He motioned me to sit by him.

I walked over and he said "Take off your skirt and heels, I slid off my heels and unzipped my skirt. I stood in front of him in pantyhose, panties and my blouse. Mario slapped the cushion next to him and I sat next to him.

I began to feel very exposed in just my pantyhose, panties and blouse. Mario quickly rubbed my inner thigh up to my semi hard cock restricted in pantyhose and panties. I moaned and quickly maneuvered me onto my back. He straddled my chest and soon his cock was near my mouth again. He began to mouth fuck me, thrusting his hips. I rubbed his ass with my hands and he continued to thrust his cock into my mouth.

Mario abruptly pulled out and looked down at me "Do you have lube? Are you clean?"

My euphoria of being a complete sissy slut took over my common sense, I nodded and whispered "yes, let's go upstairs".

Mario followed me up to my bedroom, he laid on the bed naked and hard. I went to the bathroom, did a quick enema and grabbed the lube.

I got on the bed and knelt down over Mario's cock, I sucked it and fondled his balls and Mario pulled away. He smiled and said "I might cum again if you continue. Get in doggy style on the end of the bed."

I got up and knelt on the bed, Mario got behind me and slid my panties down. He brought his tongue to the crack of my ass and licked it through my pantyhose. I moaned. I had been leaking precum into my pantyhose all night, my cock stiffened without the restrictions of my panties being on.

I felt a rip in the crotch of my pantyhose and soon a cool liquid on the crack of my ass. Mario slid one finger into me and then two. I moved my hips like a slutty girl as he fingered me.

Mario ripped a larger hole in my pantyhose and put his hands on my hips. I felt the head of his cock at the entrance of my sissy pussy.

He slowly pushed his cock into me, I gasped as he maneuvered and thrusted his hips. Mario began to increase the pace, and soon was fucking me hard! I closed my eyes and enjoyed being the sissy I was. My cock was hard under my pantyhose as he pounded me.

His breathing picked up after a few minutes, and held my hips and moaned "I'm cumming!" and I could feel his cock pulse as his cum filled up my sissy pussy.

He pulled his cock out and pulled me up. He held me from behind and whispered in my ear "Cum for me my slut, jerk your sissy cock for me."

"Lay down on the bed, face up," Mario instructed.

I laid down on the bed, Mario laid next to me, he began to whisper in my ear "Stroke your cock sissy boy, think of what a slut you were getting fucked all dressed up like a fag."

I feverishly stroked my cock, and within 30 seconds cum erupted out of my cock, it landed on what was left of my pantyhose, my blouse, etc.

Mario ran his finger through my cum and brought it to my mouth. "Lick my finger clean."

I licked my cum off his finger. Mario got up and went to the bathroom. I got up and grabbed a towel as cum was leaking from my ass down my nylon covered legs.

I slid off my heels and tried to make myself presentable again. Mario came out of the bathroom. He was dressed. He walked over and kissed my cheek. He looked at me and said "We need to do this again, this was hot."

He walked out and drove away. I stripped down, showered and slid on pantyhose and a silk robe as I went to bed.

Being a non passable Crossdresser, finding a regular is hard. You meet a lot of guys that have great sex with you, then disappear. It's the natural thing for a man to do. They have regrets, question their judgment and soon you never hear from them again.

Saturday, I tried to focus on other things as opposed to logging onto Grindr. I wanted to go on there, but I didn't want to see if Mario was on and then be ignored. Crossdressers do better with regulars who understand their needs and desires.

I waited until Monday night. I was horny Monday night, I was at my home office in a silk pajama set with tan pantyhose. I had no make up or anything on, but I was in a mood for cock.

I logged into Grindr for the first time since Friday. I had 5 messages. 3 of the usual, "Host, do you suck?" kind. One for an advertisement and one from Mario.

The first one from Mario read "You home?", then "you must not be on." then "I have a feeling I am getting ghosted." to "I really wish I could see those legs in pantyhose."

I replied, "I'm here, just busy the last few nights."

About 10 minutes later I got a reply "Sweet, I thought you ghosted me."

I replied, "I didn't want to seem too desperate."

Mario chatted back "So you enjoyed the other night as much as I did."

I sent a blushing emoji. We continued to chat about life, etc.

Mario then texted a question "What does your schedule look like Thursday night?"

I replied "Work, Work out, the usual, yours?"

Mario replied "I will be on a business trip, but driving by your place at night, mind if I stop over?"

My stomach churned, I texted back "I will be ready for you."

He sent me an estimated time and I logged off.

The next 2 days crawled, as I all could think about was dressing up for Mario.

Finally Thursday night arrived. I got home from work and slid on some black pantyhose. Over it I wore running shorts, a hoodie and my running shoes.

A lot of guys wear tights under their shorts these days, so I figured I would take a jog with pantyhose on. I was feeling sissy-like and feminine all week, getting seen by a few fellow joggers would really get me going and inspire me for Mario's visit.

I went for a run, only got one glare by a burly guy walking on the trail. I got home, showered, shaved and used an enema. I poured myself a Vodka and Sprite and got ready for Mario to stop by.

I lubed my sissy pussy and slid in my plug. I slid on a light blue thong and put on a white shaper. I slid on a pair of gray thigh high stockings and began to do my makeup. I finished my drink and decided to make another one. I walked to my kitchen in my lingerie.

I walked back to my bedroom to finish getting ready. All of sudden my doorbell rang. I ran and grabbed a robe and tiptoed to the door to look through the peephole. It was Mario. I didn't have my wig on, and my makeup wasn't completed yet.

I opened the door and Mario stared at me. He smiled and said "Wow, you don't need to put anything else on. I hate to be this guy, but it has to be quick. I actually have a co-worker in the car. She thinks I am stopping by to check out a record collection".

My heart sank a little, but I motioned Mario to follow me and I led him into the bedroom.

Mario unbuckled his pants and slid down his underwear. His cock was 1/2 hard. I instinctively knelt down in front of him and wrapped my lips around his cock. I sensually sucked his cock as he hardened. Mario pulled me up off my knees and rubbed his hands on my ass. He felt the plug in my sissy pussy and pulled it out.

Mario leaned in and whispered in my ear "bend that sexy ass over." I bent over and felt his hard cock on the tip of my sissy pussy. He pushed me down to where I was laying face down on the bed with my ass and legs standing next to the bed.

Mario put his hands on my hips and slid his cock into my sissy pussy. A tingling overcame my body, as for the second time in a week, Mario was plunging his cock into my sissy pussy.

Mario quickly developed a rhythm and my cock grew in my panties as it grinded on the mattress.

Mario spanked my ass and pounded away on me. I craved this feeling. I closed my eyes and soon my cock started to spurt cum into my panties, I rotated my hips to maximize the feeling as my cock rubbed on my mattress. I was having my first sissygasm, hands free.

Mario sensed I was cumming and fucked me harder. He pulled out and told me to "Turn around and get on your knees, you dirty whore."

Wobbly knees and all, I knelt down and Mario stuck his cock in my mouth, I tasted my own ass juices and he pulled back out and stroked his cock. "Open up your mouth, slut." After a few jerks, cum erupted from Marios cock, onto my chin, in my mouth and up to my eyes. The flow slowed down and I reached up and licked his cock clean.

Mario quickly got dressed and I finally got up from the floor. He waved goodbye and left. I shakily walked to the bathroom, and looked in the mirror.

My face was full of cum, My robe had cum on it. My panties were soaked and drying with my own cum and my nylons had cum on the knees and thighs. I looked like a used slut. I stripped down and showered, trying to refocus my mind on other things.

Over the weekend, My focus went back to dressing. I spent all day Saturday wearing tan pantyhose and red panties under my jeans as I did my weekend chores. I didn't even wear socks under my jeans on the chance someone would see my nylon covered ankle. Saturday night I slept in black pantyhose and a T-shirt.

I would pop on to Grindr, quick and pop out. On Sunday Morning, I got a message from Mario. "I have some time tonight, if you don't mind me stopping by?" My cock twitched when I read that message and I responded back "What time?" Mario responded "Around 6 pm. I have a meeting with a client, then I should be coming by. " I sent a Thumbs up emoji.

My cock hardened in my pantyhose, thinking about Mario fucking me again. I was becoming addicted to sex with him. I tried to refocus and did some things around my house and worked out. Finally at 4:00 PM, I decided I would start to get ready.

I showered and shaved my legs, crotch and face. I put on Victoria's Secret lotion, slid on a white thong and tan sheer to waist pantyhose.

I carefully did my makeup, I put on my white shaper, then a white/blue short dress. I slid on my white strappy sandals and walked to the kitchen. I poured a glass of wine and sat down. It was 5:30. I went to the bathroom and looked in the mirror. I looked pretty sexy for a CD.

I poured another glass of wine and waited for Mario to visit. At 6:30 I looked at my phone, there were no messages. Mario was either late or pulling a no show. Around 8 pm, I figured Mario wasn't coming. I took off my dress and sandals and went and laid down in bed. I was disappointed. I was horny and thought about looking online, but decided against it.

Around 9 pm I logged back into Grindr. I had 4 messages from Mario.

"Was out with co-workers, got drunk, now at home."

"My roommate is gone, get over here."

"Please, come over. I was really looking forward to tonight."

"???"

I thought about my response. I responded "Sorry, I know things happen, maybe another time."

Mario replied "I know you want me tonight" and sent a pic of his cock.

I replied "Too bad, you didn't come earlier." and sent him a picture of my outfit from before.

Mario replied "You are such a slut, you know you want my cock. My roommate is gone, unless you sucked others tonight. Did you suck a bunch of cock tonight Krissy?"

I replied, "You wish you knew, didn't you."

Mario replied "I knew you were a sissy crossdressing slut, you just love being on your knees in your panties and hose don't you?"

The verbal abuse was actually turning me on a little. I replied "I am not fully dressed anymore, I am just in panties and pantyhose."

Mario replied "We can work with that, get up and get your ass over here."

Mario sent his address and I replied "Give me a half hour."

I got up and put on a black lace bodysuit over my pantyhose and panties. I put on a sweatshirt over it, along with a pair of my jeans, I left my makeup on, figuring no one would see me. I slid on a pair of my Hey dudes and headed over to Mario's.

Mario had a Duplex Townhouse style. It was in a nice area. I pulled into his Driveway and parked behind his garage.

I buzzed in and Mario unlocked the door and said "Take your shoes off and head upstairs."

I slid off my shoes and walked upstairs. The door was open in Mario's bedroom. He was on his bed, just in his boxers.

He looked drunk, he smiled and said "Hey Krissy, How are you? Let's see what you are wearing under those jeans."

I slid my jeans off and my sweatshirt. I stood before Mario in my bodysuit, pantyhose and panties.

Mario commented "I do like that you left your makeup on." Mario motioned for me to lay next to him on the bed.

I got into bed. Mario's hands roamed all over my body, from my nipples to my nylon covered feet. Mario stood up and slid his boxers off, Mario told me to sit on the bed, I spread my legs and stood in between them.

I knew what to do, I wrapped my lips around his cock and Mario put his hand on the back of my head. I sucked his cock as he moaned and thrusted his hips. His cock was rock hard and my cock was getting harder by the second.

Mario pulled out and told me to lay on the bed. I laid down and he knelt on my shoulders. He squatted and straddled my shoulders and pulled my head to his cock. He began to fuck my mouth and started to slap my face.

Mario began to call me "Whore, fag, slut, etc." as he fucked my mouth. He pulled out and squatted on my face and made me lick his balls. I licked his balls, and his underside. I was his slut.

He told me to move my head to the end of the bed and lay down. I switched positions and he stood over and made me lick his balls as he jerked his cock. Soon, he moved his cock to my lips and grunted. "Here you go Krissy, I know you love dressing up and eating cum."

Cum erupted from Mario's cock onto my lips, nose, chin and eyes. My face was covered.

Mario pulled his cock away, He went and sat down by my pantyhose covered legs and rubbed my thighs and calves, he whispered "You have great legs Krissy, They are sexy."

I laid there with his cum on my face, but I was enjoying the massage Mario was giving me. Mario climbed over me and laid down next to me. He pushed me to my side and ground his half hard cock into my pantyhose covered ass, as he rubbed my thighs.

Within minutes Mario was snoring. I slowly got up and walked to the bathroom. I cleaned my face and rinsed my mouth. I washed my hands and dried them. I was going to quickly change and head home before Mario woke up.

I walked out of Mario's bathroom and grabbed my jeans and sweatshirt. I figured I could change in my car quickly, so I didn't wake Mario up. I walked down the stairs and to my surprise there was a man sitting on the couch.

I stood in front of this man wearing a black lace bodysuit, my panties and tan pantyhose. I still have some makeup on.

He was a larger white man, a bit older than Mario. He looked at me, shook his head and said "Is that your car in the driveway in front of the garage?"

I nodded

He replied "Well, I parked right behind it, so you are stuck. You parked in front of my garage space. I also see you are here for pleasure. Mario does like his drag fags."

I looked at him nervously and replied "Can you move your car, so I can move mine? I didn't know I was taking your spot. Mario didn't tell me."

He smiled, "Mario was probably too excited to get his dick sucked by you. This isn't the first time I have had to tell one of his fairy friends that they are stuck. I will have to say, you are one of the more feminine ones I have seen come out of this bedroom. Now if you want me to move my car, you better get on those nylon covered knees and give old Bill here a good blowjob."

I put my head down and knelt down. Bill walked over to me and unbuckled his pants. He slid them down to his knees and slid down his boxers. A huge cock popped out. He moved his cock to my lips and I opened them up.

12