Maria's First Time With A Man

I discovered crossdressing in college but was never able to fully explore this side of me. After graduating, I was finally able to completely indulge my femininity. By this time I was in my early 20's; I had grown into my full adult stature. I was 5' 10" tall and weighed 150 lbs. I worked out and was really toned. I had great abs and a great ass, and I was proud of my long slender legs as well. I had my own apartment, and more than half of my closet was given over to my female wardrobe. All styles of dresses, skirts and blouses and all types of fabrics filled the closet. I had more than three dozen pairs of shoes and boots in many different colors. The one thing they all had in common was at least a 3" stiletto heel or higher.

Three of my dresser's four drawers were given over to feminine undergarments. Bras, panties, garter belts, stockings, pantyhose, corselettes, and waist cinchers filled those three drawers. And of course, they were in every color of the rainbow. I was able to find makeup tutorials online and became even more expert until my reflection showed a very attractive woman. I discovered prosthetics and purchased silicone breasts and a silicone vagina to give me an even more feminine figure.

The type of work I did allowed me to grow out my hair to shoulder-length without causing questions. I wore it plain or tied back at work. I learned how to use a curling iron to give myself different looks. I had quite the collection of faux jewelry that included necklaces, earrings, bracelets, and rings.

Eventually, I began to notice an emptiness when I dressed. It took me quite some time to figure out what was causing this emptiness. I discovered I was wondering what it would be like to be a woman completely. What would it be like to be with a man? I never, ever had these feelings in my male persona, but Maria couldn't stop thinking about it.

I purchased a few dildos and began to experiment with them. It took a while but eventually I could take an 8" dildo completely up my ass without feeling any pain. I also learned to deep throat dildos. I taught myself how to cum without having an erection because it was impossible to get an erection inside my silicone vagina. I would masturbate while dressed and fucking myself with a dildo. Soon, that wasn't enough.

I began to enter crossdresser chat rooms dressed as Maria. I particularly looked for admirers' chat rooms. I met Daniel in one of them and we began to chat privately. Daniel was in his early 30's and was old-fashioned. Modern women just didn't appreciate him. Daniel was not into pants-wearing, aggressive women. He wasn't prejudiced and he applauded accomplished women. He certainly wasn't against them spreading their wings, he just had a thing for women who dressed the old fashioned way!

Daniel discovered crossdressers on the internet. He especially was attracted to 'passable' crossdressers who dressed very femininely. This was the type of woman he had been looking to meet, it appeared the crossdressing community most closely resembled this type of woman for him.

Daniel had the same kind of hesitancy I had about being with the same sex. While he would masturbate to pictures of sexy, cross-dressed 'girls,' he never looked at pictures of girls showing their cocks. He wanted the complete illusion that the girls he was jerking off to, looked completely like girls.

It took a while, but we decided to meet for coffee. I dressed very demurely, long skirt and poofy blouse, understated makeup, wearing the only pair of flats I owned. No pressure of any kind, just the chance to meet one another in person. We enjoyed each other's company. Daniel was kind, gentle, and intelligent. He told me he liked my sense of humor. We met for coffee a second time and from there decided to meet for Happy Hour drinks.

Late afternoon alcoholic beverages, again no pressure of any kind. I also dressed up quite a bit more. I wore a navy-blue silk skirt suit with a cream-colored satin blouse. I had on beige, patent leather 4" heels and sheer tan stockings. Underneath I wore a matching cream-colored bra, panty, and garter belt set. I was going for the 'office look.'

The alcohol loosened my inhibitions and also loosened my tongue. I know I was being kind of flirty. At one point, when I was sure no one else was looking, I slowly pulled my skirt up high enough so Daniel could see the garter tab holding up my stocking. His eyebrows shot up and I saw him licking his lips. "If you like that big boy, wait until you see the rest!"

Daniel smiled back at me and said, "If things continue to go the way they're going, I'm hopeful I'll get to see all of you in the very near future."

We decided to up the stakes and meet for dinner. We met at a hotel restaurant. The hotel had a lounge and dance floor right next door. I chose a bright red, silk wrap dress with matching lingerie underneath. My sheer, suntan stockings had seams. Daniel wore a nice suit and tie. We looked like a couple of lovebirds out for an evening's entertainment.

I ordered a small salad and brandy. Daniel ordered filet mignon and whiskey. We ate, made nervous small talk, and then moved to the lounge next door. We ordered a second round of drinks. I asked Daniel if he liked to dance. He said he loved to dance, and we moved out onto the floor.

It was the first time we had touched one another. It was magical! Daniel was an excellent dancer and we spun around the floor like Fred Astaire and Ginger Rogers from one of those old black-and-white movie musicals. The song finished, and Daniel leaned in to kiss me. He was gentle and caring, just caressing me with his lips while he hugged me gently to him. I kissed him back in the same way even though I wanted to throw my arms around him and drive my tongue between his lips.

We held hands on the way back to our table. We had more drinks and danced some more. I had never, ever felt more feminine than I did while dancing with Daniel. "Daniel. I don't want to pressure you and I'm more than willing to wait, but I'm ready. I'm ready to be with you. I'm ready to make love to you and have you deep inside me.

Daniel leaned in and cupped my chin in his hands. He kissed me deeply, this time letting his tongue slide past my lips and inside my mouth. I suckled his tongue, longingly. "I'm ready too," he said when he broke off our kiss.

We decided to go our separate ways later that evening. We didn't want to be caught up in the moment's passion and an alcoholic lessening of inhibitions.

We began to plan our evening together. Daniel had insisted upon paying for all our drinks and meals whenever we had met in person. I insisted upon paying for our hotel room. He only agreed when I pointed out I needed a lot of time to prepare myself for him and that I would be in the hotel room hours before he ever arrived.

I checked in early that afternoon and began my preparations almost immediately. Before I did anything else, I painted my nails, both fingers and toes, in a deep crimson color. When the polish had dried, I shaved my face as closely as possible. I stood in the tub and rubbed a depilatory all over my body from neck to toes. I wasn't particularly hairy to begin with, but I wanted to be as smooth as possible. I showered it off and then ran a hot floral bubble-bath as hot as I could stand. I soaked for what seemed like ages, while soaking I douched three times. I wanted to ensure I was fresh for Daniel. While my face was soft from the tub's steam, I shaved my face a second time.

I got out, dried myself off and rubbed myself from head to toe with a lovely, unscented hand and body lotion. I glued on my silicone vagina and slipped into a strapless, black lace open-bottom corselette with six garter straps. I inserted my silicone breast forms into the cups. I pulled on sheer glossy black nylons with back seams and clipped the garters to them and then stepped into black velvet mules with 4" heels.

I sat down to do my makeup. I had chosen dramatic evening makeup to go with my nails. I trimmed my eyebrows as much as I dared and put on false eyelashes. They weren't overly long but they were lush and filled out my eyelashes nicely. I finished off with crimson lip-gloss that matched my nails. I took my curling iron and gave my hair some body by curling it in waves. Finally, I lightly spritzed my favorite perfume, Egyptian Musk, inside my thighs, behind my ears and on my wrists.

I then went to the closet and grabbed a stretch black velvet mini dress. It was a halter dress with a choker collar, had an open back, and a sheer upper bodice panel that showed my cleavage underneath. When I stepped into it and zipped it up, it really hugged my curves! It came to about mid-thigh covering the welts of my stockings nicely. I put on gold dangle earrings, bangle bracelets, and rings as a final touch to my outfit.

I walked over to the full-length mirror and gasped. I had always been proud of my makeup skills, but I had outdone myself. Maria looked lush, lovely, and sexy! There was a gentle knock on the door and when I opened it, Daniel was standing there in a tuxedo with a dozen red roses! I took the roses from him and walked slowly into the room, swaying so he could get a good look at me. I arranged them in a vase while he continued to just stare at me.

"Maria, I'm tongue-tied. You look absolutely breath taking! You're gorgeous, desirable, sexy! I've always thought you were an attractive woman, but you've taken your look over the top. There's not a man in this hotel who wouldn't want to be with you tonight. Hell, there's not a man in this city who wouldn't want to be with you tonight!"

I blushed. "First roses, and now these unbelievably flattering compliments! Daniel, I do believe you're trying to seduce a lady!" I giggled, strolled up to him, laid my hands on his chest and lightly kissed him on the cheek.

I could hear him inhale and he said, "My God, Maria. You smell as wonderful as you look. I can't wait to hold you in my arms."

"Well, then let's go downstairs to the lounge, grab some drinks and start dancing. The best way to this girl's heart, and into her panties, is out on the dance floor!" I laughed, Daniel groaned but gave me his arm and escorted me to the elevator. The elevator had mirrors. I was leaning gently back against Daniel's chest. I inched the hem of my dress above my stocking tops so Daniel could get a good look in the mirror. "Like what you see big boy? I'm going to wrap these stocking-covered legs around your waist while you're fucking me uncontrollably later on tonight!" Daniel couldn't talk, he was staring at me as he licked his lips.

We got a small booth by the dance floor and ordered drinks. I sat next to Daniel and placed my hand on his thigh. He looked at me with big eyes and I blew him a kiss. Our drinks arrived and as we sipped, we made happy small talk. I was getting lots of looks from single men in the lounge, but I only had eyes for Daniel.

'Baby, Come To Me' by James Ingram came on and I squealed. Daniel knew what that meant. As he helped me out of the booth, I deliberately let my dress ride up so only he could see my stocking tops. I smoothed my dress down and he led me to the dance floor. Our dance was slow, sensual, and romantic. Everyone else left the floor to watch us. I looked at Daniel with passion in my eyes and sang the words to him.

'Baby, come to me

Let me put my arms around you

This was meant to be

And I'm, oh so glad, I found you'

When the song ended, I leaned in and kissed Daniel firmly. I was letting him know I wanted him now! Suddenly, there was a round of applause from everyone who watched us dance. Blushing, I quickly pulled Daniel back to our booth. I had my hand on his thigh again but was letting it wander towards his crotch. "Baby, let's finish our drinks and go back upstairs. I can't wait any longer, I have to have you inside me." My painted nails stroked Daniel's now hard cock.

Daniel placed his hand on my leg and began to rub my nylon-covered thigh. He leaned in and kissed me again. "Maria, this is so hot. I'm taking you back to the room right now!" He helped me out of the booth, and we walked to the elevators arm-in-arm, my head on his shoulder.

Once inside the room, I turned around and wrapped my arms around Daniel's neck. I pulled him to me and pressed my lips against his hungrily. I was grinding my crotch against his magnificent erection. Daniel cupped my ass cheeks and pulled me to him. He kissed me back just as passionately. We stood like that for what seemed an eternity but was in reality, only moments.

I stepped back from Daniel and reached up to unfasten the collar of my halter dress. I let it fall to my waist so he could get a good look at my silicone breasts being held up by my lace corselette. I reached behind me and unzipped my dress slowly; it was so quiet in the room you could hear the zipper coming down. I let my dress fall to the floor, stepped out of it and kicked it away from me. I stood before him wearing only my lingerie, stockings, and heels.

Daniel groaned with an audible gasp. "Maria, you're even lovelier than I had fantasized. You are the woman of my dreams."

I stepped back into his arms and kissed him again, this time with even more urgency. I told him, "Now I'm going to undress you. Please relax and follow my lead." I knelt in front of him and helped him out of his shoes and rolled his socks off him. My hands reached under his pants cuffs, and I caressed his calves. I leaned down and kissed the tops of his feet and ran my tongue in between his toes.

Daniel was groaning as I stood up, letting my nails run gently over the hardness bulging inside his pants. I helped him out of his jacket and shirt and hung them in the closet. I came back and began to kiss his stomach and chest, taking first one and then the other nipple between my painted lips. "Maria, Maria, ohhhhhh, Maria!" was all he could say.

Then I unbuckled his belt, slid his zipper down and helped him out of his pants. I hung these in the closet as well. I was moving slowly about the room so Daniel could get a good look at me in my lingerie, stockings and heels. Finally, I came back and knelt in front of him to help him out of his boxers. "Once I take these down, this cock is mine. There's no turning back. If you're having any second thoughts at all, now is the time to leave."

Daniel looked longingly into my eyes and said, "The only place I'm going, once you take these boxers off, is into your bed."

I slid his underwear off, gently kissed his cock, and got into bed on the top of my sheets. I stared into his eyes and asked, "Well?"

Daniel joined me and I asked him, "How do you want to do this baby? What position do you want me in?"

He whispered in reply, "I want you on your back, missionary style. I want to be on top of you and I want to be looking into your eyes when you cum for me!"

I couldn't roll over onto my back quick enough. I placed a pillow under my hips, raising my ass to Daniel. "There's some lubricant on the nightstand, baby. Put some on my ass and on the tip of your cock. Take this pussy, take it now!"

Daniel did as I asked. I could feel him lubricating my asshole and hear him squeezing some onto his prick. I lifted my ass up as he placed the head of his bulging 6" cock against my love hole. I've had longer dildos inside me, but Daniel's cock was thick. He gently began to slide himself inside me as I groaned and squirmed. He eased inside me until his balls were resting against my ass cheeks.

"Oh Daniel, this is everything I always imagined and more. I love the feeling of your hot cock filling me up. This is what Maria has been missing. Fuck me, baby, oh fuck me, Daniel. Fuck me like the woman I am. Fuck me like the woman you want!"

Daniel began to fuck me v-e-r-y slowly. He would bury himself inside me and then back out until just the head of his cock was inside me. He never changed pace, never picked up speed, he was like a metronome the way he pistoned in and out of my ass.

I had wrapped my nylon-covered thighs around his waist. My stiletto heels were dug into the cheeks of his ass, and I cupped his ass with my hands trying to pull him into me harder, faster. But Daniel just continued that maddeningly, slow steady pace. I couldn't believe the feeling of his cock going in and out of me, especially as his prick came close to leaving me but always stopped just inside the entrance to my 'pussy.'

"Daniel, you're driving me crazy. Please, please, PLEASE fuck me FASTER, fuck me HARDER, fuck me, fuck me, FUCK ME!"

Still, Daniel just fucked me slowly, I could feel his rock-hard cock inside me. No matter how I squirmed, pushed, or pulled, Daniel fucked me steadily. The feeling of that cock inside me, taking me almost as mechanically as my dildos but hotter and more throbbing than anything I ever had inside me before, pushed me over the top. I had the most intense orgasm I'd ever had in my life up to that point.

"Fuck, FUCK! I'm cumming, I'm cumming, I'M CUMMING for YOU Daniel! I'm cumming for you, Daniel. You're MAKING me cum for you! Take me, take this pussy, TAKE ME, fuck, fuck, FUCKKKKK!!!!!"

Daniel didn't change speed, he just continued to fuck my asshole at that same, steady pace. I collapsed underneath him. Moaning, groaning, I couldn't utter an intelligible word. Finally, Daniel stopped with his cock buried inside me. He leaned in and began to kiss my face everywhere. Lips, cheeks, neck, ears, eyelids, it was SO hot!

"Daniel, Daniel, Oh-My-Gawd Daniel! That was incredible!" I cooed into his ear. He looked into my eyes with an almost guilty look. "What's the matter, baby? What's wrong? That was fucking insanely erotic. I've never had a better orgasm!"

"I cheated." he said.

"Cheated? What the hell do you mean? That doesn't make any sense. You just gave me the best orgasm of my life and you tell me you cheated?"

Daniel looked at me sheepishly and said, "You're so fucking hot I knew I wouldn't be able to control myself and I'd cum too fast. I also got a room in the hotel so I could be close, and I jerked off in my shower earlier, twice, thinking about you. I knew I wouldn't cum so fast that way." Daniel blushed.

"Oh baby! That's not cheating." I laughed. "That's so thoughtful and so amazing. Now I want to make you cum!" I rolled Daniel onto his back and knelt between his legs. I began to lick the mixture of lubricant and cum from his shaft. I even cleaned the slit in his prick with my tongue. He was moaning and bucking his hips while I did this. Then I began to fondle and kiss his balls. I took first one, then the other inside my mouth. I ran my tongue over them while I sucked very gently on his sack.

"Maria, oh baby, that feels so incredible. Your tongue and lips are amazing."

He was still hard, and I began to deep throat him. I had practiced on dildos that were longer until I was able to get all of it inside my mouth without gagging. I ran my tongue up and down his shaft and swirled it around the underside of his prick. He began to fuck my face and I thought he was getting close to cumming so I climbed on top of him.

Daniel guided his throbbing member inside me again, this time I was on top, and I was going to control the pace. I began to ride Daniel's cock in the same rhythmic manner that he had fucked me. Daniel started rubbing his hands up and down my nylon-covered legs. The feeling was incredible. I had always loved touching myself this way but to have another person, a man, rubbing his hands up and down my stockings while he was fucking me was so erotic.

I began to slide my pussy up and down Daniel's cock. I would bury it inside my ass and then begin to lift up until just his prick was inside me. Then I'd slide back down his shaft s-l-o-w-l-y until he was completely inside me. I started to rotate my hips while I was riding his cock, first one direction, then the other. I placed my hands on his chest, gently pinching his nipples which became erect almost instantly. I leaned down and started sucking them and Daniel really got excited.