Ever since I was a little boy I've always loved wearing girl's clothes. I remember going through my mother's lingerie drawer and trying on her panties and bras. I loved the way the silky sheer material felt against my body. As I got older I had less opportunities to indulge in my fetish until I got married. When my wife was away or at work I would wear her panties and bras while I masturbated. Luckily she was as tall as I was so the fit was pretty close. I would encourage her to buy plenty of sexy lingerie knowing that I would be wearing them later.
My wife and I eventually divorced and I moved out. It was not easy being on my own again especially being in my 30's but I was able to rediscover my fetish with the help of internet shopping. I could buy all of the women's panties and bras I wanted and they would arrive at my door without anyone knowing my kinky little secret. I collected all kinds of sexy panties, garter belts and thigh high stockings. I even started to buy dresses and perfume and would spend my day taking a long hot bath, shaving my legs silky smooth and then trying on my sexy clothes. I grew my hair long, wore makeup and could easily pass for a woman. I ordered a big fat dildo with a suction cup base that I would use to fuck my ass with. I love dressing up as a hot slut, wearing makeup, setting up my dildo and fucking myself silly, all the while pretending that I was a sexy girl getting fucked by a big stud.
I would ride the dildo with my eyes closed whispering, "fuck my ass" to my imaginary lover. I like wearing sexy lingerie under my regular clothes and going out in public. The feeling of the sexy panties and bras under my clothes keeps my cock hard as I go about doing my daily errands and I always have to jerk off when I get home. One day, I was walking through the supermarket and I squatted down to look at something on one of the lower shelves not realizing that the sexy pink panties with the ribbon tie up the back that I was wearing were peaking out of the back of my jeans. I stood and walked down the aisle passing a good looking guy who was smiling at me. I smiled back but thought that maybe he was just kind of a weirdo. The guy turned back and walked up behind me and whispered, "I like your panties."
I was so busted. I turned to him and said, "Excuse me?"
"It looks like those panties you're wearing are pretty sexy. Maybe you'd like to show me them."
My face burned with embarrassment. I tried to look away but couldn't.
"It's laundry day. They're my girlfriends," I said.
He laughed loudly. "Bullshit."
"Alright. They're mine. I like to wear women's panties. Big deal."
"Hey it's cool. I think it's hot. I'd really like to see what you're wearing under there."
I smiled and blushed. "Oh yeah?"
"Yeah, my name's Rajeev"
"I'm Jeff. Listen I'm not gay or anything, it's just a little fetish of mine."
"Uh huh. Sure," he wasn't buying it. "Who said anything about being gay? I just want to see what you're wearing under those clothes."
I thought about it for a second. Nobody had ever seen me dressed as a girl and the thought of it was really turning me on. "Why don't you follow me back to my place and I can put on a little fashion show for you," I said.
Rajeev followed me back to my apartment. I made him a drink and told him to make himself at home while I freshened up. Just to tease him a little bit I stripped down to my bra and panties and I walked into the bathroom. I put on some sexy makeup, topping it all off with bright red lipstick. I put on a pair of white thigh high stockings, a white garter belt and a pair of sexy white bikini panties. I then put on a lacy white bra and slipped a pair of falsies into them to make it look like I have tiny tits. I slipped on a pair of red high heel pumps and a flirty white summery sundress. I checked myself in the mirror and had to admit the transformation was quite remarkable. I looked just like a pretty girl. I took a deep breath before leaving the bathroom.
The look on Rajeev's face as I entered the living room was priceless. His eyes were practically falling out of his head and his mouth was on the floor.
"Like what you see?" I asked.
"I-I can't believe it. You look amazing. If I didn't know it was you I'd say you were an incredibly beautiful woman."
"Thank you." I did a little twirl, my sundress lifting up a little exposing my stockings and garter belt.
"Wow," Rajeev replied. "Do that again."
I spun around again, bending over a little so he could see my ass. He grabbed his crotch and shifted in his seat a little.
"What's going on over there?" I asked.
He unzipped his pants and pulled out his cock. It was about seven inches long, really thick and hard as a rock. Now my jaw was on the floor. I've never seen another man's penis before and I couldn't believe how beautiful his was. I stood there hypnotized by it.
"Like what you see?"
"Uh-huh," I stammered.
Rajeev stroked his cock slowly. I held my legs together, feeling my own erection growing in my panties.
"Why don't you take that dress off for me?" Rajeev asked.
There was no hesitation as I slipped the sundress from my shoulders and let it fall to the floor never taking my eyes off of Rajeev's cock.
"Turn around," he demanded. "Show me your ass."
I turned around, cupped my titties and bent over for him. I looked between my long legs and watched as he stroked his cock a little faster. I got on all fours and pulled my panties down a little, exposing my clean-shaven asshole to him. He gasped and stroked his cock harder. I turned around and crawled over to him on my hands and knees. I kneeled before him and took his cock in my hand. It was rock hard and almost hot to the touch. I gently stroked it, marveling at its length and girth. I leaned forward and licked the tip just as a drop of precum appeared. It twitched in my hands and seemed to grow bigger and harder. I put the head of his cock into my mouth and sucked on it gently. I've never been more excited or aroused in my life. My own cock was sticking out from the top of my panties. I reached down, pulled it out and started to stroke it.
Rajeev put his hand on the back of my head and pushed his cock all the way into my mouth. I made my mouth as wet as possible savoring the feeling of his hot, hard cock as it pumped in and out of my mouth.
I couldn't contain my excitement as I jerked my own cock and came hard into my panties. I now concentrated my efforts on Rajeev's cock. I bobbed up and down on his dick trying to milk the sperm from his balls. Rajeev pulled his cock out of my mouth and rubbed it around my lipstick-smeared lips, teasing me. I grabbed it and put it back into my mouth, deep-throating him. Rajeev threw his head back and moaned loudly as a hot load of cum filled my mouth. I jerked his cock and let his sperm slide down my throat. It was the single most erotic experience of my life. I licked every last drop of cum from his cock wishing there was more. Rajeev zipped up his pants and stood up.
"Listen, I have to go but I'd really like to see you again," Rajeev said.
I looked up at him with sad puppy dog eyes.
" I'm not blowing you off, I promise. I'll give you my number and address. Please tell me you'll come over later."
"Okay," I said.
He wrote down his number and address and told me to be there at ten o'clock PM, dressed to the nines. I agreed and kissed him lustily on the mouth as he left.
I spent the rest of the day pampering myself as if I was I woman. I took a long hot bubble bath and shaved every inch of my body. I rubbed a sexy smelling body cream all over my skin making it soft and silky to the touch. I put on my makeup, did my hair and chose my outfit for the night. I decided to wear all black. I slipped a pair of sheer black thigh high stocking up my silky smooth legs fastening them to a sexy lace garter belt. I put on a lacy black bra and matching panties and then slipped into a little black cocktail dress and a pair of black patent leather high heeled pumps. I packed a few things into an overnight bag just in case things went well and left my apartment. I had to be careful that none of my neighbors saw me otherwise I'd have some explaining to do but I made it to my car without anyone seeing me and drove to the address that Rajeev gave me. I walked up to the front door, rang the doorbell and was immediately buzzed in. I walked up the stairs and saw that Rajeev was waiting for me at his door. He kissed me as I entered.
"I wasn't sure you were gonna show."
I reached down and grabbed his cock through his slacks.
"You give me some more of what you gave me earlier today and I'll come over anytime you want."
I felt his cock grow bigger in my hand.
It was then that I realized we weren't alone.
"I hope you don't mind but I invited my friend Deepak over to join us."
Deepak stood up and walked over to us. He was a little taller than Rajeev and had the most piercing blue eyes I have ever seen. He looked lean and muscular and I knew that this was going to be an interesting night.
"Uh, sure." I managed.
"I'm Deepak. It's nice to meet you."
He kissed me on both cheeks.
"Why don't you come over and sit on the couch."
They were being such a gentlemen that it put me totally at ease.
"Okay." I said as I walked over to the couch and sat down.
Rajeev and Deepak sat down on either side of me. There was a bottle of wine and three glasses poured on the table in front of us.
"Would you care for some wine?" Rajeev asked.
"Sure." I said.
He handed me the glass and I sipped from it nervously.
"What about a toast?" Deepak asked.
"Oh, I'm so sorry." I replied.
"Here's to making new friends." Deepak said.
We all clinked our glasses and drank. I couldn't believe I was sitting in between two unbelievably attractive men dressed. I loved every minute of it because they made me feel like a sexy woman. Deepak casually put his hand on my knee sending an electric shock up my leg.
"So...I'm sorry I don't know your name." Deepak said.
I thought for a second. "Priyanka. My name is Priyanka."
"Priyanka. That's a beautiful name."
"Thank you." I felt myself blushing.
"I have to say Priyanka, you look absolutely stunning tonight." Deepak said.
Rajeev put his hand on my other knee, "You look even better than this afternoon."
I batted my eyelashes and soaked up all of the attention that I was getting from these two sexy men.
I took another drink from my glass of wine and noticed that it was starting to have an effect on me as my head began to spin a little. Rajeev leaned in and kissed my lips, which were still wet with wine. I met his kiss and felt him put his tongue in my mouth. Deepak started to run his hand up my leg parting them a little. He slipped his hand up my dress and massaged my inner thigh. I broke my kiss with Rajeev and turned my head and started to kiss Deepak. Rajeev took my hand and put it on his leg as he started to rub my other thigh. My head was really spinning now but not just because of the wine. I moved my hand up Rajeev's leg and found his cock hardening through his pants. I put my other hand on Deepak's leg and slowly moved it up to his lap. When my hand touched his cock I had to break our kiss because I couldn't believe what I was feeling.
"Is that your cock?" I asked, "Or are you just happy to see me."
Deepak just smiled and started to kiss my neck and then stuck his tongue in my ear. This put me over the top. I unzipped his zipper and put my hand inside his pants. I grabbed his cock and pulled it out into the open air. I couldn't believe how enormous it was. It was at least nine inches long and almost as thick as my wrist.
"Oh my God," I whispered. "I can't wait to have this in my mouth."
I held it in my hand and squeezed it causing Deepak to moan loudly in my ear. Meanwhile, Rajeev had freed his own cock and I jerked him with my other hand. I leaned back into the sofa and massaged these two beautiful cocks as Rajeev and Deepak both removed their clothes. I stood up in front of Deepak and leaned over him licking the tip of his cock. I took the tip of his cock into my mouth and wondered if I could possibly take much more. I kneeled between his legs and sucked on the head of his cock. I massaged its thickness, trying to take as much as I could into my mouth.
Rajeev got up from the couch and moved behind me. I felt him push my dress up around my hips exposing my panty-covered ass. He massaged my ass cheeks and started to pull my panties down. I was so enthralled with Deepak's cock that I wasn't paying too much attention to what Rajeev was doing until I felt him lick my pink little asshole. The feeling was indescribable as Rajeev stuck his tongue into my ass. He got my asshole nice and wet and then I felt him put a finger inside me. My asshole clenched around his finger as I sucked Deepak's cock with abandon. When Rajeev unzipped my dress, I leaned up and pulled it over my head and then went back to work on the gorgeous cock in front of me.
Rajeev took his cock and started to rub it in between my ass cheeks. I took Deepak's cock from my mouth and looked back at Rajeev.
"I don't know if I'm ready for that. I've never been fucked before."
"I'll be gentle," he said.
I looked at him with fear in my eyes but the way he was massaging my hips and ass as he rubbed his cock against my asshole felt so good that I didn't care if he was gentle. I took Deepak's cock back into my mouth and bobbed my head up and down. I felt Rajeev put the tip of his cock against my ass and push. He went slow as the tip of his cock entered my ass. It hurt for a minute and I whimpered around Deepak's cock, "Oh God, please go slow."
He slowly pushed his entire cock into my ass and then just as slowly pulled it out. This gave me some time to get used to it and I moaned all over Deepak's cock.
"You like that baby?" Rajeev asked.
All I could do was nod my head as I sucked on Deepak's member. Rajeev slapped me playfully on the ass and pushed his cock into me hard. I winced at the pain and cried out, "Oh, yeah. Fuck me. Fuck my ass."
Rajeev really started to fuck my ass as he grunted and groaned behind me. Suddenly, he stiffened and pushed his cock all the way into me. He came inside me with a loud moan and I felt his sperm soak my insides. He slowly slipped his cock out of my ass and wasn't long before I felt it leak out of me and down my leg. I crawled onto Deepak's lap kissing my way up his stomach and chest and finally deeply on the mouth. He aimed his giant cock at my asshole and I was still so lubricated by Rajeev's juices that I slid down on it almost effortlessly. I say almost because it was so god damned big I felt like it was going to split me in two.
Even with the ass fucking Rajeev just gave me I was having a hard time taking Deepak's entire monster. I started to ride him very slowly as I got used to his size. My own cock was so hard as it pressed between us. Deepak grabbed my cock and started to stroke me. It didn't take long before I was shuddering with an orgasm. My jizz hit his stomach and chest. I totally started to ride his cock now and I could sense that he was nearing an orgasm. I clenched my asshole and pumped his cock by just moving my hips up and down the best I could. Suddenly, he stiffened and I sank down all the way onto his shaft. He came inside me with a loud grunt and I felt his come fill me. I collapsed onto his chest and just let him fill me as much as he wanted. His cock softened and slipped out of my ass slowly. I got off his lap and retreated to the bathroom to clean up.
When I came back out into the living room both Rajeev and Deepak were getting dressed. I found my panties and put them back on along with my dress.
"Well, I should probably be getting back home." I said
"Why? It's the weekend. Why don't you spend the night?" Rajeev asked.
"Really?" I asked.
"Of course," he replied.
"Just don't expect to get much sleep," Deepak added.
I giggled. "Well, okay. Why don't you boys get into bed and I'll slip into something more comfortable."
I was really glad that I packed an overnight bag as I again retreated to the bathroom to change. I slipped into a sheer pink silk and lace babydoll with matching panties and made my way to the bedroom. Both men were in bed waiting for me when I got there. I got in between them and was immediately enveloped in their masculinity. I spooned Rajeev as Deepak spooned me. His hard cock was nestled between my ass cheeks and Rajeev's cock was hardening in my hand as I massaged it. My own cock was hardening and poking into Rajeev's ass. We stayed that way for a few minutes just dry humping each other. I slipped under the covers and started to suck on Deepak's cock and much to my surprise Rajeev slipped under the covers as well and took my cock into his mouth. The feeling was indescribable as Rajeev pulled my panties off and completely engulfed my cock.
I really wanted Deepak's cock back in my ass so I slid back up into our spooning position and Rajeev followed. Deepak rubbed his cock up and down my asshole. I pushed back and felt him slowly enter me. I found Rajeev's cock and pumped him slowly as Deepak fucked my ass. My own hard cock was sliding in between Rajeev's ass cheeks when suddenly Rajeev pushed back and my cock slipped into his ass. He froze for a second and winced in pain even though I wasn't nearly as big as they were. Every time Deepak pushed his cock into my ass, my cock went deeper into Rajeev's. I jerked Rajeev's cock as I fucked his ass and felt him tense and then come all over the bed sheets. Deepak was fucking my ass really hard now when he grabbed my hips and pushed all the way into me with a loud grunt, filling me with his seed. He pulled out of me, which allowed me to concentrate on fucking Rajeev. I slammed my cock into his ass several times and finally unloaded into him. My cock slipped out of his ass and eventually we all fell asleep, completely spent.
When I woke up the next morning I was completely alone in the bed but the smell of coffee and bacon filled the air. I slipped my panties back on and went into the other room to find Rajeev and Deepak cooking breakfast.
"Good Morning," Rajeev said.
I just smiled and said, "Good Morning."