I have been enjoying women’s clothing for about 10 years. I am now 45 and still get excited with the feel of silk against my skin. I am married but when I am alone, I dress as a woman. I have a complete wardrobe which I have hidden in my attic. I have gotten very good at putting on makeup and though I would not pass as a woman, I don’t look that bad.
Recently I have had a strong urge to be dressed with another man. I have been communicating with another man on the internet and have had some very open and hot discussions.
Last week we decided to meet. He planned it out so we would meet at a local mall. We would meet at one of those outdoor coffee spots and if we decided we liked each other, we would proceed from there. I agreed to it and as the day got closer, the more excited I got yet the more cautious I got. I put together my wardrobe and things in a bag and put it in my car. I was still unsure as I drove to the mall.
Once inside I went to the coffee shop and I saw him. He said he would be wearing a red windbreaker. He was also about my age but he looked younger. I walked up to the table and he stood and shook my hand. “Well, it is finally nice to meet you face to face,” he said with a grin. We ordered some coffee and just started talking. I really liked him and we both seemed very comfortable with each other. We talked about work and actually about everything but what we were there for. That sort of made it easy to get to know each other. He had dark hair, blue eyes and a very strong face. He was pretty well built with a little gut. He was actually very handsome. As we talked I was visualizing him under his clothes. I must have been daydreaming when he said, “Hello, are you still here?” I immediately stammered some excuse and he just laughed.
“Should we get out of here?” he said calmly.
“I guess so,” I replied. We got up and walked down the mall.
“I got a room here at the Ritz here in the mall,” he said. “I can write it off to business,” he said with a grin.
“I need to get my bag,” I said. He handed me a second room card and said, “925.” He left for the hotel and I went and got my bag. I was shaking like a tree. I wanted to do this but was still so nervous. I was sweating all during the elevator ride.
I got off on the 9th floor and went to 925. My hand was shaking as I put the card in. The light turned green and I pushed the door open. I walked in. “I was afraid you had changed your mind,” he said. “Almost,” I replied. “Would you like a drink,” he said walking to the small room bar. “Sure, got any scotch?” I asked. “Coming up,” he said pouring a glass. I took the scotch and sat down on the couch. “Good,” I said sipping it. “Why don’t you go change,” he said boldly. “Ok.” I said getting up and grabbing my bag. I walked into the huge bathroom and closed the door. Well, it’s now or never I thought.
I stripped out of my street clothes and decided I better shower too. I took a quick shower and dried off. I looked into the mirror. What am I doing, I thought. But I knew I wanted this to happen. I looked at my body. I had trimmed my leg hairs very short and had actually shaved my ass before coming. I put some light powder on my body and stepped into a pair of black silk panties. I automatically got a hardon. I slipped my garter belt on and then slid my stockings up each leg and hooked them. I put on my bra with the silicon breast inserts.
I sat down at the counter and looking in the mirror, I slowly put on my makeup. Lipstick, eye shadow, penciled my eyebrows and put on a little cover makeup and blush. I stood up and stepped into a short skirt, put on a white blouse and then stepped into my black high heels. Lastly, I put on my blonde wig and my earrings and necklace. All done and very pretty I must say so myself. Now I just had to get up my courage to walk out that damn door. “Hey, what’s keeping you?” he heard him say through the door. Well, here goes.
I opened the door and walked out. He just stood there looking at me. “Wow, you look beautiful. You were not lying when you said you thought you looked ok dressed,” he said He took my hand and walked me to the couch. I sat down very ladylike and he handed me my drink. “A toast to you,” he said raising his glass. We talked a bit, like a man and woman. I noticed he kept looking me over. I crossed my legs a couple of times like a tease. I was really doing it up right.
“Can I kiss you?” he asked. “I ahhhh guess,,” I said unsure about this. He leaned over and lightly kissed my lips. It was nice. He slid over closer and kissed me again. This time longer and then he pushed his tongue between my lips. I liked it and kissed him back. Our tongues moved against each other. He put his arms around me and kissed me very passionately. It felt good. My cock was straining against my panties. “Oh, you are delicious,” he said as he leaned back. My lipstick was all over his mouth.
I put my finger to his lips and wiped a little off. I then leaned forward and ran my tongue over his lips. He opened his mouth and we began kissing again. His hands moved to my blouse and he played with my fake tits. He then moved his hand down and around my back and cupped my ass. It felt good. He took my hand and placed it on his crotch. My heart began to pound as I felt his hard cock against my hand. I squeezed him. He was huge. What had I gotten myself into?, I thought. I continued to stroke his cock and then I knew I wanted to touch it. As he kissed me, I undid his belt, unbuttoned his pants, pulled his zipper down and put my hand inside his pants. His cock throbbed. I wrapped my fingers around it and slowly stroked him. I moved my thumb over the head of his cock. I had to feel it bare.
I broke our kiss and slid to the floor. I untied his shoes and took them off. Then removed his socks. He lifted his hips and I pulled his pants off. He sat there in his shirt and briefs. His cock pressed against his cotton briefs. He parted his legs and I moved up between them. I lay my head against his briefs. My face was touching his cock. His cock, I can’t believe it……..his cock. I turned my face and brought my lips against the material. I kissed his cock through his briefs. I cupped his balls. They were also big. I couldn’t wait.
I reached up and slowly pulled his briefs down and over his cock. His cock popped forward and hit my chin. It was smooth and hard. He had a large mushroom shaped head that was dark purple in color. I wrapped my hand around it and leaned in and kissed the head. I drew my tongue around the head and his shaft. It felt wonderful. Hot, smooth..mmmmmm. I had to have him in my mouth. I opened my mouth and brought his cock to my lips. I surrounded the head with my lips. Oh god, it felt fantastic. Here I was. Dressed as a woman, on my knees in front of a man and sucking his cock. His big wonderful cock. I pushed more into my mouth and sucked on him. He began to move his hips and moan softly.
“Yes, suck me,” he moaned. I pumped his cock in and out of my mouth. I fucked his cock with my mouth. I pulled my mouth off and pushed his cock up. I moved down and licked his big balls. I took one into my mouth and ran my tongue around it. I lifted his ball sack and ran my mouth under it. I could smell the musky odor of his ass. I let my tongue slide into his crack. I could just barely lick his ass. I could not get to his hole, though I wanted to. I moved back up to his cock and stuck him back into my mouth. I sucked and ran my tongue all around his cock. I wrapped my fingers around his shaft and pumped him as I sucked. He groaned and rolled his hips as I sucked on his big, hot, juicy cock.
I wanted him to cum. I wanted his cum. I needed his cum. I sucked and pumped his cock. My spit coated his cock and made it slick. He started raising his hips and shoving more of his cock into my mouth. He was so big and it was hard to take any more of him. Several times his humping shoved his cock deep into my throat and I gagged. He was too big. I wanted all of his cock in my mouth and throat but I could not take it. So I just pumped him faster and faster as I sucked. I felt his cock tighten and swell. He was going to cum. He raised his hips and groaned as hot, sticky cum filled my mouth. I kept sucking and swallowing his thick sperm. He continued to fill my mouth with his cum. I swallowed and some ran down my chin onto my blouse. I couldn’t get enough of it. It was hot and sweet and filled my mouth. I keep pumping his cock and sucking up his cum. My tongue and mouth were coated with his sperm.
Then I felt my own cock leak my cum. I shot my cum into my panties, again and again. I continued to softly suck his softening cock. Getting all of his cum, every last drop. I pulled my mouth off and licked the head of his cock. He told me to stop, it was too sensitive. I did. I sat back on the floor and licked the remaining cum from my lips. “No, wait,” he said as he slid down to the floor and kissed me. He licked my lips, tasting his own cum. He pushed his tongue into my mouth and I shared what remaining cum I held in my mouth. He was hot and passionate as he kissed me.
“That was fantastic,” he said. “I know, I know,” I replied. “My first cock, my first cum, I love it.” I sighed. “Get me a drink,” I asked him. “Sure, sweetheart,” he said getting up. He got me a scotch and I sat back down on the couch.
I crossed my legs and sipped my scotch. I felt like a woman. I loved sucking his cock. I loved being treated as a woman. Though a woman with sticky panties. He sat down in a chair across from me. “You were wonderful,” he said. “I have never cum so much. I loved your mouth and feel.” “I loved your cum,” I said. I recrossed my legs and let my skirt ride up my thigh. I could see he was looking up my dress.
“You like what you see?” I said with a smile. “Yes, yes I do,” he said. “Well, maybe a little later. After I finish my drink.” I promised. “Why don’t you take off your briefs so I can look at your cock,” I directed. He stood and pushed his briefs off. Even soft, his cock was big. He took his shirt off and sat back down naked. “That’s better,” I said.
He moved off his chair and sat on floor at my feet. He drew his hand up my nylon cover calf. “Your really are very pretty,” he said caressing my leg. I uncrossed my leg so he could see up my dress. He moved closer and placed his lips on my leg. He kissed my nylon covered leg. His lips moved higher on my leg. He grabbed my legs and softly pulled my ass to the edge of the couch. He pushed my skirt up and kissed my bare thigh just above my stocking. I was getting hard. He moaned softly as he kissed and lightly licked my thigh.
“Would you like to kiss my pussy?” I asked him. “Oh yes, please,” he replied. I stood up and pulling my skirt up to my waist, I knelt back on the couch with my ass towards him. He brought his lips to my thighs and kissed them. Then he kissed my ass cheeks through my panties. He pressed his mouth and nose against my silky panties and ass crack. I felt his tongue against my panty. He pushed me more forward until I rested my arms on the back of the couch. He pulled my panties to one side and ran his tongue up my ass crack. It felt exciting and erotic. He pulled my ass apart and slid his tongue between my cheeks. He ran his tongue up my crack until he found my asshole. Oh god, it felt wonderful as his tongue invaded my hole. He licked me and pushed his tongue into my ass.
“Yes, tongue fuck me,” I said loudly. “Eat me.” He pushed my cheeks further apart and tongue fucked me. I could feel his hot wet tongue slide into my ass. My cock was straining against my panties. I was in heaven. God, I was so fuck’n hot. He just ate my ass up. He reached around and grasped my cock. He stroked my cock while fucking me with his tongue. I was on fire. I knew then what I wanted. What I needed. What I was going to have. I looked over my shoulder and said, “Darling, take me to the bed and fuck me.” He looked up at me and stood. I slid off the couch and he took my hand and walked me to the bed.
He turned me to him and kissed me. I wrapped my arms around him and pushed my tongue into his mouth. We kissed so passionately. His hands slid down my back and he pulled my skirt up over my ass. He cupped my ass cheeks and pulled me into him. “Now,” I said. “Fuck me now.” He pushed me back onto the bed. I pulled my skirt up and he reached up and pulled my panties off. He climbed up and straddled my chest. I pulled his hard cock to my mouth and sucked on him. I licked him and spit on his cock to get it wet. He moved down the bed and knelt on the floor. I pulled my legs up and he started licking and kissing my ass.
I felt his first finger enter me. “Oh, yes,” I moaned. He fucked me with his finger and then, put a second one in. I felt my asshole stretch. It hurt a little but I was so fucking hot. He pumped his finger in and out of my hole. Then I heard him spit and add a third finger. “AAHH,” I groaned as his fingers went it. My hole stretched and little by little I began getting used to the feeling. And the feeling was wonderful. “Darling, please fuck me. Put your cock in my pussy,” I begged him. He spit one more time and then moved up and put my nylon covered legs on his shoulder. I reached down and found his cock…. It was so hard. I moved it to my ass hole. He reached down and grabbed it from me and pressed it against my hole.
“Oh god,” I cried as I felt the first pain. He pushed the head of his cock just inside my hole. “AAAHHHHHH,” I groaned. “Stop, STOP,” I pleaded. He leaned down and kissed me. “It will hurt a little, my love.” he said softly. “I will go slow.” He waited until I grew accustomed to the size and then slowly pushed a little more in. “Slow, slow,” I panted. Little by little he would push and pull his cock in and out of my ass. Each time a little more of his cock entered me. I was feeling so hot and just the thought of getting fucked as a woman made my cock hard.
“Yes, darling, fuck me. Fuck me,” I encouraged him. He pushed all of his cock into me and then I felt so full and his balls on my ass. “Yes, now fuck me.” I demanded. He began to push in and out of me…….to the hilt. I felt my own cum run out of my dick onto my stomach. I was getting fucked and cumming. He pushed his cock hard in my ass. I reached up and grabbed his ass, wrapped my legs around his waist and pulled him hard into me.
“FUCK ME,” I cried out. He pounded my ass, over and over again. My nylons stuck to mysweat covered legs. My ass rose to meet his cock. Over and over he fucked me. Then, grabbing my ass, he pushed hard into me and came. I felt his cum fill my ass and run down my butt cheeks. He groaned and continued to slide in and out of me, filling me with cum and also pulling cum out with each stroke. My ass was covered in hot sticky cum. And my own cum covered my stomach. I reached down and scooped my cum off my stomach and brought it to his lips. He sucked my cum off my fingers and licked his lips. He then leaned down and kissed me. Pushing his cum coated tongue into my mouth.
“Oh my love. I loved the way you fucked me. I am your woman,” I whispered in his ear. “I want you to fuck me all night.” His cock slid out of me as he pushed my legs off him and lay beside me, panting. He was covered in sweat. I was too, but he was naked. My clothes stuck to me. I lay there in my wet blouse, garter belt and stockings, high heels and cum. Hot sticky sweet wonderful cum. But I was satisfied. Sucked my first cock, ate my first cum and just got fucked as a woman. And there was more to cum… and that’s not just a pun either. Stay tuned.