The Dresser Files Ch. 1

"Can I get you anything?" she said with a slight smile. "Sure, let me have a bourbon and ginger ale." I replied. She turned and walked back up the aisle. I leaned over and looked at her as she walked away. I just love flight attendants. She had a tight ass and a cute sway as she walked. I envisioned her sweet ass covered in a tight pair of silk panties. I had to laugh to myself. Being a crossdresser, I was not sure if I was lusting after her ass or her underwear. One of the advantages of flying is people watching, especially nice assed stews.

"Here you go." she said handing me my drink and taking my four dollars. Taking my first sip, I looked around at the people seated next to me. An older man probably on a business trip was highlighting some sentences in a memo. Two young girls were laughing about something and the guy next to them slyly kept eyeing their young firm tits. Not right next to me, but in the window seat was a very attractive woman. She wore a tight skirt, nice shoes and a white blouse. The blouse did nothing to hide her large breasts. I love breasts. I could just...wait, I'm getting away from the story.

Anyway, here I am on a flight to good ole Texas. Let me step back just a little. About a month ago I wrote a story about my crossdressing, my first fling with a man and posted it on a website. I got a lot of feedback from it. One especially intrigued me, so I returned her email. We communicated back and forth over the weeks. I had a business trip out to Texas, so I told her I would stop by to see her. She said that would be great. So here I am. Thirty thousand feet in the air, drink in hand and heading for Tejas.

I must have dozed off because the next thing I knew was the stewardess tapping me on the shoulder. "Please bring your seat up and fasten your seatbelt," she said. Wow, we are in Dallas already. The plane shuttered as the wheels touched down and we taxied to the gate. I went and grabbed my bags and got a rental car. It really is amazing how travel is today. Four hours earlier I was in Washington DC and now I am driving on a Texas road. Man, Dallas/Ft. Worth is a huge metropolis. And on a Saturday, the traffic was terrible. I had the directions she gave me lying on the passenger seat so I just calmly drove and looked at the scenery. I love Texas. Still a little outspoken, cowboys in cowboy hats and cowgirls in tight fuck'n jeans. Everywhere you looked were pretty women and a few attractive guys too. I am not partial to what type of tight butt is in those jeans.

Well, after about an hour, I turned into a nice development. Texas developments are great because each house is pretty different from the next. Not like the single mold homes in DC. I took the next left and looked for the house number. There it was. A nice looking ranch house with a beautiful lawn. I pulled into the driveway and got out. I was really anxious to she what she looked like and what her personality was, face to face. I got out of the car, stretched and walked up to the door. The doorbell button was missing so I knocked. I waited a minute and knocked again. Nothing. I told her I was coming in today. There was a car in the driveway so I assumed someone was home. I knocked again, but no one came. I tried the front door knob and it turned. I slowly opened the door and said, "Hello!" Nothing. So, I went in. What a nice home. Very neat and comfortable. I looked in the living room, kitchen and a big bedroom. No one. I then heard some music downstairs. I slowly walked downstairs and heard music coming from a room. The door was slightly open so I peered in. Was I in for a shock!!!

There was a young guy about 20 or 21 years of age standing naked with his back to me. He was digging through some items on the bed, some clothing. The next thing I saw was him holding up a pair of woman's panties and pressing them to his face. Then he slipped them up his legs and snugged them up over his ass. Mmmmmm. I felt my cock harden. I was very quiet and watched. He pulled on a pair of thigh high stockings and then reached for a bra. He tried and tried to get it around him but there was no way. It was too small for him. He threw it on the bed and walked over in front of a mirror. He ran his hand over the legs and panties. He turned to look at his ass when he looked up and saw me.

"WHAT THE FUCK?" he shouted in a scared voice. "Whoa, wait a minute." I said raising my hands up. "WHO THE FUCK ARE YOU AND WHAT ARE YOU DOING IN MY HOUSE?" he said loudly and grabbing a shirt to hold in front of him. "I came to see Jan," I said trying to calm him down. "She lives here doesn't she?" I asked. "Yes, that's my mom," he said stammering. "Who are you?"

"I am a friend from Washington and was just stopping by. I'm sorry. I knocked but no one answered and the door was open." I continued. "Well, you had no right to come into my house and especially into my room." he said. I could see he was nervous and embarrassed about being caught in women's underwear. "Look, I'm sorry I intruded, but don't be embarrassed. I wear women's clothes at times too." I said trying to settle him down.

"I'm so embarrassed." he said. "Don't be." I replied and walked into the room. I walked over to the bed where there were several pairs of panties, a slip and the bra. I picked up the black lacey bra. 34C. "You will never get this on." I said holding up the bra. "Though these are nice size tits, you are quite a bit bigger around the chest. We guys have that problem with women's lingerie," I said holding a pair of the panties to my face. They smelled wonderful and used. The scent of perfume and the scent of a woman's pussy. "Look, I'm Glenn." I said extending my hand. "I'm Curt." he said. He shook my hand but still held the shirt over the front of him with his other hand. "I'm going out to the car for a second." I said as I walked out the door. Wow, I thought to myself. I was lucky I didn't get shot or beat up. I was also very lucky to see that nice ass on that young kid. He was not real handsome but a nice looking guy. And with just a brief glance, I think he had a decent size cock too. I went to the car, opened the trunk and grabbed my "special" suitcase. I always have two. One with my regular clothes and the other, my special collection of my femme attire.

I went back in the house and downstairs. When I got to his room, he had got out of the panties and stockings and was wearing a t-shirt and pair of shorts. I walked over to the bed and put my suitcase on it. I unzipped it and threw the top open. "Take a look." I said. He walked over and looked into my suitcase. I could see a smile come to his face as he looked at all the silk items; Bra's, panties, slips, stockings, garter belts, shoes, make-up, a couple of skirts and blouses and a couple of different color/style wigs. "This is yours?" he asked holding up a light blue chemise. "Yes, all of them." I replied. He ran his hand through the lingerie and sometimes holding up at item. He seemed to be interested in the garter belt. "Ever tried one of those on?" I asked. "No, but they sure are sexy." he said. "Would you like to try it on?" I said. "I would like to dress you."

"I I'm, ah ah, not sure." he said nervously. "You will love it." I said. "Well, ok." he said while again running his fingers through all the silk. "Oh, I forgot, where is your mom?"

"She had to go to Waco for the day. I don't think she knew you were coming." he said. "She should be home later tonight though."

"Ok, Curt, go take a shower." I said. "All my clothes are clean and you need to feel the silk against your clean skin." He was getting excited because he quickly left the room for the bathroom. I picked out some items and lay them out on the bed. I was getting excited too. My cock was straining in my pants. About ten minutes later he came back in wearing his shorts. His hair was shiny from being wet. "Ok, first, go get me your razor and soap." I directed. He returned with them. I pulled a chair into the middle of the room and had him sit in it. "We are going to get your chest smooth." I said applying the shaving cream to his chest. I shaved the little hair he had off his chest and around his nipples. His nipples got very, very hard. I wiped off the excess cream and then I ran my fingers over his nipples. I squeezed them a little. "Do you like that?" I asked. "Yes, I feels good." he sighed. "Ok, stand up." I said. "Take off your shorts and underwear." He stood but was reluctant to take them off.

"Hey, I've seen plenty of dicks." I said tugging at his shorts. He stepped out of his shorts and underwear. His cock was still limp but pretty impressive. I handed him a pair of his mom's black panties. "Don't put them on." I said. "You always put the garter belt on first so you can pull your panties down or off without unhooking the garters." I grabbed the garter belt and reaching around his waist, hooked it. I got a pair of black stockings and kneeling in front of him, slipped each one up his legs. I thought, next time I will shave his legs. I knew there would be a next time. I hooked one stocking to the garter belt. Then the other one. I told him to put on his mother's panties. He stepped into them and pulled them up over his hardening cock and his smooth ass. I could see his cock getting harder. He was very conscious of it and tried to turn sideways.

"Hey, don't worry. There is not a man alive whose cock will not get hard by slipping on a pair of silk panties," I said with a laugh. He turned back and I smoothed his stockings in place. I let my hand slide against his cock as I stood up. "Now, one that will fit you." I said reaching for one of my bra's with the silicon breast forms. I put his arms through it and hooked it in the back. I could tell he was getting excited. I brushed myself against his ass as I walked back in front of him. "You look delicious." I said scanning him from head to foot. "Now, let's do some finishing touches," I said taking him by the hand and sitting him in the chair.

I grabbed my makeup kit and started with a little foundation. Then I did his eyebrows with a dark pencil, a little mascara, some eyeliner and shadow and a hot pink for his lips. He looked edible. I had him stand up and gave him a short black skirt, which he slipped on. He put on the white blouse I gave him and tucked it into the skirt. "These may be to big, but we can put some paper in the toes," I said handing him a pair of black pumps. They were too big but some kleenex stuffed in the toes did the trick. "And lastly," I said as I pulled a short blonde wig on his head and tucked in his dark hair. Man, was he hot and was I proud of my work. He turned to look in the mirror. "Walk around." I said. He slowly walked around the room, always looking back into the mirror as he passed by. "Well, what do you think?" I said.

"Oh, I feel so good and sexy." he said strutting around his room. "And excited?" I asked. "Yes, very excited." he said. "I will have to get used to walking in these shoes though."

"Hey, you got a beer or something," I asked. "Sure, upstairs." he replied. "Let's go." I said heading out the door and up the stairs. He followed and we went into the kitchen. He opened the door of the frig and bent over to get the beers. His ass was so tight in that dress. My cock was straining to get to it. He closed the door and handed me a beer. He kept slowly walking around. First, to probably get used to the pumps, but also to savor the feeling of being a woman. I know that feeling. You get hotter every moment. That is what I was hoping for. "Let's go into the family room." I said.

We went in and I sat on the couch. He sat in a chair across from me. "Cross your legs sometimes." I said. "It's a very sexually feeling." He did and it was sexual; for me. Man, he was hot and virgin. At least I hoped so. "Come over here a minute." I said. He got up and swayed over. "Stand in front of me," I said. "Turn around." He turned around and his ass was in front of my face. I reached up and rubbed my hand across his ass. What a tight butt. I cupped his cheeks. "That feel ok?" I asked. He softly said yes. "Sit by me." I said patting the cushion beside me. He sat down and I just looked into his eyes. "Can I kiss you?" I asked. "I'm not sure about this." he said. " I know I ah" I cut off his sentence by pressing my mouth to his. He didn't pull away. I continued to kiss him and slowly pressed my tongue against his soft lips. Then I pressed my tongue between those tender lips and into his mouth. Little by little he responded by pressing his tongue against mine. I could hear him softly sighing. I held his head in my hands and continued to French kiss him. Running my tongue over his lips and teeth and pushing it deep into his mouth. "Oh yes." he moaned. "Yes." He could not get enough of my mouth and tongue.

I reached for his hand and pulled it to my crotch. "Rub my cock." I whispered in his ear. He slowly caressed my cock through my pants. "I've never felt another man." he whispered. "It's ok." I said softly. Each time his caress got a little firmer. Soon he grasped my hard shaft. "Undue my pants." I softly said. He undid my belt, unbuttoned my pants and slid the zipper down. His hand found its way inside my pants to my cotton covered cock. He explored every inch of my cock with his hand. Soon his fingers were under the underwear and his was stroking my bare hard cock. "That's it, love my cock." I said leaning back. He broke our kiss and stared down at his hand. I reached down and pushed my pants open, baring my hard cock. I could see his tongue run over his lips as he looked at my cock. "Go ahead. You want to." I said pushing his head down to my lap.

I felt his breath on my cock and then his tongue. He licked the head and shaft. Slowly. Softly. My cock was filling with blood. Getting harder. The head was turning a deep purple. I felt him slip the head into his mouth and suck on it. I could hear his heavy breathing and moans. Sliding off the couch, he knelt between my legs. I could see his sweet face and his hot pink lips circle my cock. "Suck me, baby. Suck me." He slowly took more and more of my cock between his young hot lips. His tongue bathed my cock with his hot and wet salvia. He was getting real good at sucking cock. I felt my nuts tighten. I wanted to shoot my cum into his mouth; her son's mouth. I only wish she was here. I know she would love to be watching. Watching him suck my cock, while he was wearing her panties. I raised my hips to move my cock in and out of his mouth. He stroked my cock with his hand and sucked on the head of my hot cock. "Yes, god that's so good." He kept forcing more and more of my cock into his mouth. Once or twice he took it all. His mouth was pressed against my pubic hair.

I felt it coming. My cum was ready to explode. Explode in this young virgin's mouth. I humped my cock in and out of his lips. He was getting hotter and began to frantically suck my cock. He pulled his mouth off my cock and looked up at me. "I want you to cum in my mouth. I want to taste your cum," he said turning back to my cock and sliding it between his lips. I reached down and held his head and began pumping my cock in and out of his mouth. He slurped and sucked. Wetly. Hotly. Then, I felt my balls tighten and my cum rise up my shaft. He gagged a little as I filled his mouth over and over with hot sweet cum. He sucked and swallowed. It seemed he could not get enough. He was possessed. Sucking and pumping my cock to get all of my sperm, he moaned loudly. He wanted all of my hot juice. His lips were coated with my cum. Drops hung from his chin. God, he was good. I have not cum that much in a long time.

As my cum subsided, he continued to suck on my cock. Taking it out of his mouth, he licked me clean. Lightly sucking on the head. Licking some of the cum that dripped on my balls. He even pushed my legs up to get some that ran under my balls and also to my asshole. I reached down and pulled him up to the couch. I pulled his face to mine and kissed him. Tasting my own cum on his sweet lips and tongue. I held him, and loved him. I kissed him softly. I wanted him to know how wonderful it was, he was. I wanted him to know it was all right. I wanted him to feel as good as me. "That was so wonderful," I said holding him. "You look so beautiful and you were so hot."

"Let's go to your room." I said standing up and pulling my pants closed. I took his hand and we walked downstairs. I walked him over to the bed and had him sit down. I sat down beside him and kissed him. He let my tongue invade his mouth and caress his tongue. "I am going to love you now." I said. I continued to kiss him and slid my hand down his leg and up under his skirt. He moved his legs apart as my hand moved up his leg. I felt the silkiness of the stocking and then the warm dampness of his bare thigh. He shuttered as my hand crossed his thigh and touched his panty covered cock. He was hot and hard. I could feel a damp spot on his panties from his pre-cum. I stroked his cock through his panties as he moaned into my mouth. I broke our kiss and pushed him back on the bed. I pushed his skirt up, pulled his ass to the edge of the bed and pushed his legs apart. Oh god he looked good. Lying there in the black stockings and panties, legs spread apart and his cock pushing against the black silk. I kissed his stocking leg and up to his thigh. I licked and sucked on his soft moist skin. I drew my tongue over his damp flesh and up to his panties. I sucked the head of his cock through his panties. I could smell him and Jan on the silk. His hips rose to press his cock against my lips. I sat back on my legs and pulled his panties down. His raised his hips to help me pull them over his ass cheeks. Once down his legs, I pulled them off and threw them on the bed.

I looked up his legs to his hard cock. God, I wanted that cock in my mouth. I moved up, kissing his leg until his balls touched my nose. I could smell his sweet musk. I licked his balls and pushing his ball sac up, I pressed my tongue under his balls and slightly into his ass crack. I moved back up to his cock and smothered his shaft with kisses and licks. I don't know how or why, but some movement caught my eye. Not turning or moving my head, I looked up over his thigh into the mirror on his closet door. In the reflection I saw a woman standing slightly against the bedroom door, peering in. Just out of sight. It had to be Jan, his mother. I wonder how long she had been there. What had she seen? What would she do? Her actions told me what she would do, nothing. She had a hand under her skirt while she watched. Well, I was not going to deprive her.

I moved my mouth back to his cock, her son's cock, and slid the head into my mouth. He moaned out loudly and his ass cheeks contracted. I slowly took more and more of him into my mouth. Bathing his cock and shaft with my salvia. I sucked and sucked his hard sweet cock. His balls felt large in my hand and I caressed them as I made love to his cock. He kept raising and lowering his ass to my mouth. Fucking my mouth. I pulled my mouth off his cock and pushed his legs back. His ass spread and I eyed my target; his dark rosebud asshole. I drew my tongue up his crack to his hole. I licked around it, pushing my tongue in the sweet crack.. I pressed the tip of my tongue against his hole and it gave way a little. My tongue was fucking his asshole. He smelled musty and sweet. He tasted like sex, hot sex. I continued licking and tongue fucking his ass until he cried out "Suck my cock, please!"

I dropped his legs back to the bed and gobbled up his cock. I sucked it deep into my mouth and began to mouth fuck him. I pressed my finger to his wet asshole and shoved it in. He groaned as my finger slid into his ass fully. I fingered his ass as I sucked him. Then I put a second finger into him and began to finger fuck him. His hips rose and fell as I sucked and fucked him. "Yes, yes." he moaned. Before the next "yes" came out of his mouth, I felt his hot sperm shoot across my tongue. Spurt after spurt of sweet cum filled my mouth. I swallowed quickly, but could not keep up with the amount of hot juice filling my mouth. I felt it seep over the corners of my mouth and run on my chin. I continued to shove my fingers deep into his ass causing more cum to explode in my mouth. Each time I shoved my fingers deep into his hot asshole, his cock would reward me with another gob of hot cum. God, was I hot. My cock contracted and I began to cum in my pants. I savored his cum and locked my lips around his cock to suck all of his sperm. I loved the feel of the hot sticky sperm coating my tongue and lips. I drank my fill until his cock began to slowly soften. I continued to run my tongue around his cock head and shaft, getting all of his last cum. His cock slipped from my mouth. I licked my lips and some cum off his thigh.