Maria Fucks Her High School Friend!

Luke was taking a long weekend to go back to his hometown. Both of my parents are deceased and none of my sisters live there anymore. It was my 15th High School Anniversary. I hadn't gone to any of the others; I had pretty much lost touch with the few high school friends I had. I just figured WTF, my feminine alter-ego Maria had changed my life and my confidence level. I was way more confident with who and what I was.

I arrived on Thursday, mid-afternoon and checked into my hotel room. I brought two suitcases and a garment bag with me even though I would be checking out Monday morning. Maria requires way more clothing than Luke and I wasn't going to leave her behind. After unpacking, Luke went downstairs to get a drink at the bar and checkout the hotel. The bar was centrally located, the restaurant was on one side and the lounge with a dance floor, HAVE to have a dance floor, was opposite.

I ate an early, and very light dinner at the restaurant and went back upstairs to my room. Maria wanted to go dancing tonight!

I went through my familiar routine. The first thing I always did was to paint my nails, so they'd have plenty of time to dry. After my nails had dried, I rubbed a depilatory all over my nearly hairless body from the neck down. After showering it off, I shaved my face closely with a straight razor. I ran the hottest tub I could stand with a flowery bubble bath and climbed in to soak. While soaking, I douched three times to be as fresh as I could be down there. Maria wasn't planning on having company tonight, but you never know what might happen. I shaved my face a second time while still in the tub, the steam rising from the tub always allowed me to shave even closer.

After luxuriating in the scented water, I finally climbed out to dry off. I briskly toweled myself from head to toe. I patted my torso with an unscented body powder and rubbed an unscented body lotion on my arms and legs. I sprayed my favorite perfume, Egyptian Musk, on my upper thighs, behind my ears, on my throat and on my wrists. I pulled on my prosthetic silicone body suit. It had a lifelike vagina and breasts, and an open bottom.

I pulled on my black satin waist cincher with eight garter straps. I had decided to go braless tonight, my silicone breasts would stand out even more. I rolled the reinforced heel and toe, midnight black, sheer stockings up my legs and attached them to the garters. I slipped on my black satin, open toe, 4" stiletto heels and began to put on my makeup. I always put on my makeup while wearing my lingerie, stockings, and heels. It just made me feel more feminine that way.

I had become very accomplished with makeup. Years and years of practice, online tutorials, and the advice of the experts at various transformations services had really honed my makeup skills. Maria's beautiful face began to peer back at me as I continued to apply the various creams and powders. The final touch for this evening was a crimson lip gloss to match the nail polish I had already applied to fingers and toes.

I went to my garment bag and pulled out a Diane Von Furstenberg silk, black wrap halter dress. I slipped into it. My cleavage was clearly visible, my back was completely bare, and it came to about 2" above my knees. It was definitely sexy but also definitely not slutty. I put on gold dangle earrings, gold bangle bracelets, and four gold rings. I wore the rings on the pinky and index finger of my left hand, and the middle and ring finger of my right hand. I admired myself in the mirror, twirling and strutting to make sure I couldn't see any flaws. I grabbed my black silk clutch purse and headed to the lounge.

I walked up to the bartender and introduced myself. "I'm Maria. I'm staying here this weekend. I hope you have Korbel Brandy, it's my favorite." He smiled at me and pulled out an unopened bottle. He poured me a drink and I took it to a table right next to the dance floor.

I was sipping on it when I felt a hand on my shoulder. I turned and looked into the face of my best friend from high school! Luke panicked momentarily but Maria took over. I smiled sweetly into Joshua's face and said, "May I help you?"

Josh said, "I'm so sorry. This sounds so lame but for a moment I thought you were one of the older sisters of my best friend from high school, Luke. You look so much like them but clearly, you're much younger than they are."

"That's sweet of you to say...." I knew Josh's name but had to pretend I didn't.

"Joshua, but my friends call me Josh. I don't even know if Luke is going to be here this weekend, that's his name. He hasn't been to any of the other reunions, so he probably won't be to this one either even though it's our 15th! I'm sorry, here I am rambling on about things you don't even know about."

"It's OK, Josh. Would you like to sit down and join me?"

"I'd love to, but I'm supposed to be meeting a group from our reunion."

"Would you like to sit with me until they arrive. And I'm Maria." Time had been more than kind to Josh. He'd lost all of his teenage acne, his once skinny frame had filled out, and he'd become ruggedly handsome. He still seemed a little socially awkward but that was attractive in a nice way.

"Thank you, Maria. That's very kind of you."

I signaled the bartender to send a waitress. She brought Josh's drink without him having to order. "It would appear you're somewhat of a regular here. You sit down and a drink magically appears." I laughed and Josh laughed with me.

We chatted amiably as we continued to sip our drinks. Josh said, "If I hadn't just met you, I'd swear I knew you. You're just so easy to talk with, like an old friend."

I blushed and smiled sweetly at Josh. "I feel the same about you, Josh. You're a sweet man."

Just then, Josh's group arrived. I could tell without looking. I remembered that loud, obnoxious voice as if it was yesterday. Roger was the school jock who had gone off to college on an athletic scholarship. He'd also been prone to being a bit of a bully, especially with us boys who weren't quite so athletic. I'd heard his college career wasn't nearly as successful as high school, and he'd slunk back to our hometown in disgrace, at least in his own mind.

"Hey, Josh! Who's the hot babe? Didn't know you had it in you!"

Josh stood up and I looked over my shoulder. Time hadn't been quite as kind to Roger. His hairline was already receding, and his once athletic body was now more than a little flabby.

"Roger, this is my new friend, Maria. She's just passing through town and was kind enough to let me sit with her until you guys got here." He turned back to me and said, "Thanks, Maria. I hope you enjoy your stay in our town." With that, he led the group of men and women to a much larger booth. All high school classmates, some I remembered. Some I didn't. No one recognized Maria!

I was sipping on my second drink, enjoying the music, when I felt a hand on my shoulder again. I turned and was staring into Roger's leering face. "Hey Maria. I see you sitting here all alone, moving to the beat. Would you like to dance?"

I wanted to say no but thought Roger would cause an ugly scene if I did. I thought saying yes and then going back up to my room would be the prudent thing to do. "I'm getting awfully tired, Roger. I was just getting ready to go to my room for the night, but I'll dance one dance with you."

He put his clammy hand on my bare back and led me onto the dance floor. Much to my chagrin, the music changed from up-tempo to a slow beat. Roger smiled. It was not a nice smile. He held out his arms and I moved in to dance with him. He pulled me close. We were holding one hand and I had my other hand on his shoulder, hoping to hold him as far away as I could. He had his other hand on my hip. He wasn't a great dancer, but he wasn't horrible either. At least he didn't step on my feet!

Roger kept trying to pull me close to his chest. I blocked him with my free arm as much as possible. He slid his hand from my hip and began to caress my ass cheek. "Roger, please stop! Stop now or I'll make a scene." He pulled me close to him and began to tongue my neck and ear. It wasn't pleasant in the least! I was pushing away furiously when I felt Roger's grip break.

Looking up, I saw Josh holding Roger in some sort of martial arts hold. He had his wrist bent and was holding Roger's arm behind his own back. "Roger, why do you always have to be such an asshole? Go back to our group."

He let Roger go and I was just staring at Josh. This was not the timid high school friend I remembered. Clearly, he'd had some martial arts training. "I'm so sorry, Maria. Roger has pretty much stayed the same as he was in high school, a socially clumsy bully."

"Josh, I don't know how to thank you! I'm going to go up to my room so you can get back to your classmates."

"Maria, I hope this doesn't sound too forward but please let me walk you there. I wouldn't put it past Roger to try and sneak after you."

"Thank you, Josh. I appreciate that so much."

We got on the elevator, and I pressed the button for my floor. We walked down the hallway to my door, I opened it and when I turned to thank Josh, he leaned in and kissed me full on the lips! "J-Jo-Josh, no, no, no!"

Josh immediately backed away, looking crestfallen. He was never much of a ladies' man in high school, and I could see the old hurts on his face.

"Oh, Josh! It's not that, it's not that at all. I'm so sorry. Please come into my room. I can't explain out here in the hallway."

Josh looked confused but came into my room as I held the door for him. "Please have a seat while I get us both a drink." I poured myself a double and gave Josh a beer from the wet bar. I stood on the other side of the room from where he sat in his chair.

"This is going to be a l-o-n-g story, Josh." I said to him in Maria's voice.

"I couldn't let you kiss me without telling you the truth." I said to him in Luke's voice.

Josh's eyes opened wide. "Luke? Luke? Holy shit, is that you Luke? Did you have one of those operations?"

"No, Josh." I had switched back to Maria's voice. "Josh, Maria is part of me, a big part of me and a big part of my life. But I haven't transitioned. There's a large part of my life I never shared with you when we were best friends growing up."

I told Josh about being curious about my sisters' clothing and how I began to experiment with wearing their clothes. I told him my crossdressing history, about my first clumsy attempts at makeup, about how excited I was to be able to have my own personal wardrobe after graduating college. I told Josh about my discovery of female prosthetics and how I had progressed from a glue-on silicone vagina and breasts to a full silicone body suit with an open bottom.

I told him how my male self was never remotely interested in men but as my femininity began to blossom, I knew I was missing something. I had to know what it felt like to seduce a man and make love to him. I told him I had been with a few men over the years but only when dressed as Maria. Luke didn't consider himself gay, had never been with a man, and Luke had only ever dated women.

"That's my story, Josh. All those years growing up together and I just couldn't bring myself to tell my best friend I was a crossdresser. I was so afraid you'd think I was some kind of freak. I didn't have many friends growing up, Josh, you know that! You were the best and I didn't want to possibly drive you away and lose your friendship."

Josh just listened attentively while I poured out my heart to him. When I finished, he asked, "Should I call you Luke or Maria?"

"Maria please. When I'm dressed like this, please call me Maria."

"Maria, that's an incredible story. I don't know if you've ever thought about this before, but you look so much like your youngest sister, Rachel. You sound just like your middle sister, Theresa. And you have the outgoing sexy confidence of your oldest sister, Christina."

I sat there dumbstruck. I had never thought about it before, but Josh was right. Clearly, I had subconsciously patterned myself after my three older sisters.

I got us both another drink and I sat down across from Josh. We began to catch up on each other's lives, laughing and teasing one another the way we used to do in middle school and high school more than fifteen years ago.

Josh got this weird look in his eyes and said, "I'm still stunned I couldn't tell it was you, Luke. Can you show me what you look like underneath your dress? I mean, I'm having a tough time believing all this even after hearing your voice."

"Um, Josh, are you sure you want to do this?" I asked with a great deal of trepidation.

"Oh, come on, Luke. I mean, Maria. I've seen you without clothes on. It's not like we never saw each other naked in PE class at school."

I had to admit he was right, but this wasn't the same thing; it wasn't even close to being the same thing. But this was my high school best friend and he had saved me from the high school bully downstairs in the lounge.

I reached behind me and unfastened the halter top of my dress. It fell to my waist leaving my silicone breasts completely exposed. "Holy shit, Maria. Those look real. I can't tell the difference. Is it OK if I touch them?"

I had to laugh to myself, Josh's social clumsiness was in full bloom. I stepped in front of him and said, "Sure, Josh. It's OK."

He reached out hesitantly, clumsily and began to squeeze and feel my breasts. "I can't tell the difference; I really can't tell the difference."

I stepped back from him, unzipped my dress, and let it fall to the floor. Josh gasped and said, "If Luke wouldn't have said anything and you let me go ahead with what I was planning, I never would have guessed you weren't a genetic girl. You're way hotter than any woman I've ever been with."

Maria blushed uncomfortably, picked up her dress and put it back on. There was a very awkward silence. Finally, Josh fake coughed into his hand and said, "Well, I guess I better be going. Are you, I mean is Luke, coming to the reunion party tomorrow?"

"I thought I would but now I'm not so sure. It's been so awesome to see you Josh, but seeing Roger reminded me just how much I didn't enjoy high school. I don't know any of those people anymore. I'm not sure I'd have any fun. I'll think about it, but I just don't know."

"I understand." he said. "I'd better go back downstairs and rejoin the group before they get the wrong idea."

I kissed him gently on the cheek, thanked him again, and locked the door behind him.

I poured myself another drink. I stayed dressed, I was too busy thinking about everything that had just transpired. I was lost in my thoughts. There was a gentle knock on the door. I looked at the clock. More than an hour had passed since Josh left. I looked out of the hotel door's peephole; Josh was standing there.

I opened the door. "Did you forget something, Josh?"

"Yes, I forgot to tell you how fucking sexy you are, Maria, and how much I want to be with you! I hope you'll let me in and make love to me the way you did those men you told me about!"

"JOSH! Are you sure? Are you sure this is something you really want? I'm not sure how I feel about sleeping with my best friend from high school and Maria loves being with her man."

"I'm sure. I couldn't think about anything downstairs except how hot you looked standing in front of me with your dress off. And at the risk of ruining this whole thing, I had crushes on all of your sisters. I used to masturbate thinking about being with them. And to be able to be with a woman who has the best traits of all three of them rolled up into one person? I think that sex would be mind-blowing!"

"Same old, Josh." I laughed. "Telling a woman you want to sleep with her because she reminds you of her hot sisters. You never were very good at talking to the girls in high school, I see nothing's changed."

Josh blushed and looked at his shoes. I'd hurt his feelings. "I'm sorry." he said and turned to walk away.

"Joshua James McKinney!" I said it just the way his mother used to when he was in trouble. I reached out, grabbed his hand and said, "You go to my room immediately!"

He looked at me hopefully and I pulled him inside. I shut the door behind us and locked all of the security locks on the hotel door.

I turned my back to him and said, "It's your turn. Unzip my dress." While he was unzipping me I once again unfastened the halter top. I dropped the dress on the floor and stepped past him into the room. I turned and faced him so he could get a good look at Maria in her lingerie, stockings and heels.

He approached me hesitantly. I stepped inside his arms, molded my body to his, and kissed him, hard! Josh was still unsure of himself. I stepped back and asked him, "Baby, are you sure you want to do this? I'll understand completely if you leave now but please don't get me all worked up and then decide you can't go through with it. I'm so fucking turned on right now; if you left, I would be so frustrated and unfulfilled. I want you, Josh. I want to suck and fuck your brains out."

"Maria, I want this more than I can begin to tell you. I just don't want to do anything that would make you unhappy or not add to your pleasure."

"Then follow my lead, Josh." I stepped up and kissed him again hard. He threw his arms around me and kissed me back just as hard. I opened my lips and stuck my tongue inside his mouth. When I pulled back, his tongue followed into my mouth. I was licking and sucking his tongue while we made out passionately. "That's it big boy!" I cooed as I stepped away from our embrace.

I unbuttoned his shirt and took it off. This was not the chest I remembered from high school PE class. He was ripped and loaded with lean muscle. I moved in again and began to lick and suck his nipples. Josh was shivering with delight as his nipples became rock hard. While I was suckling him, my hands wandered down to his waist. I unfastened his belt and unzipped his pants. He was moaning in delight as I rubbed his raging cock through his boxers. "Ooooohhhh, Maria, ooooohhhhh. Yessss, yessss, yessss."

I knelt in front of him and took off his shoes and socks. I pulled his pants off and threw them onto the pile of our clothing. Reaching under his boxers, I cupped and massaged his ass cheeks while I licked and sucked at his erection through the material of his boxers. "Oh shit, oh shit, oh shit, Maria. I'm going to cum, I'm going to cum, I'm going to cum."

I whisked his underwear off and took him into my mouth. I repeatedly pulled his hips towards me; I was fucking my mouth with his cock. While I was slurping, licking, and sucking him, Josh put his hands on the back of my head and pressed himself to me moaning. "Nnnnnnn, uh, uh, uuuuuuuuuhhhhhhhhhh." was all he could manage to say. He exploded inside my mouth; hungrily I drank all of his cum. I didn't stop until his orgasm subsided, and he was spent.

I stood up and embraced him. He hugged me back fiercely. "Maria, that was incredible. No one has ever made me feel that way. I'm sorry I came so quickly. I couldn't control myself; you were amazing."

I smiled at him and said, "Don't apologize, honey. Every woman likes to know how much her man appreciates her." I led him to bed. We laid down in each other's arms, kissing and cuddling. I was running my fingertips all over Josh's body while we kissed. He was doing the same to me. I lightly brushed my fingertips over his testicles and up and down his thighs. He was trembling with delight, and I could feel his erection starting to grow again.

I grabbed my tube of edible lubricant from the nightstand and finished getting him hard by stroking the lube onto his shaft. "Have you ever tried doggy style, Josh?" I cooed as I got on my hands and knees. I wiggled my ass seductively and he got on his knees behind me. "Maria, I've never done it this way. Most of the girls around here don't even suck cock very well."