Fantasies of a Crossdresser

All characters are over 18

I let in a sharp inhale as I felt the blunt tip of the dildo enter me. I closed my eyes as I slid down the rubber shaft and imagined myself riding someone, anyone. I picked up speed and rocked my hips, my erection hardening, I began to stroke myself, spearing my ass down on the molded penis. I started to moan, my thoughts showing me as a lithe, well toned woman, chestnut hair in loose curls bouncing on my shoulders as I got fucked by my imaginary man. I shuddered as I came, my sperm spilling from my cock as I lowered myself with the dildo buried deep inside me and I caught my breath.

"Fuck," I thought to myself, "I need to feel that for real. "

I slowly raised myself off the fake cock and looked down at myself, the only thing similar to what I saw when I closed my eyes was the hair. I'm about average height, a little on the heavier side, but I love feeling feminine. I was dressed in a faux leather dress that I had pulled up around my hips, my breast forms were slightly falling out of the bra because I don't glue them on and my softening cock, it was bigger hard but kind of embarassing when it was flacid, what can I say, I'm a grower not a shower.

I got undressed and stared at my naked body in the bathroom mirror; I'm not ashamed of my body, I'm not trans, I just like feeling and looking pretty and sometimes, sometimes I feel like I needed to be fucked like the woman I imagine myself to be. I pull on some sweatpants and a hoodie and walked to my office and sat down infront of my computer and turn it on. I bring up a dating site and log in. I start scrolling through the pages of profiles, men, women, trans; cocks, pussies, assholes, naked bodies scroll by as I glance through the options. I keep absentmindedly scrolling until I see him, he's tan but not dark, chisled cheek bones and a gently sloping jaw, wearing a tight white collared shirt and grey slacks with a subtle outline of his package and I catch myself staring and I click on his profile. I find myself cycling through his photos until I see skin, well toned pecs and a six pack, hair but not too much, his adonis belt disappearing behind the waistband of his boxer briefs, a bulge gracefully stretching the fabric and I feel my mouth start to water and I wonder what it would be like to run my fingers through the hair on his chest as I sit on his bulge rocking my hips as I stare into his eyes. Before I can convince myself not to, I click the message link and compose him a message.

The next thing I know, I'm in a short leather skirt, thigh high stockings, tall fuck me heels and a red slimming body suit and sitting at a booth in a diner looking at a text from Chris and a picture of what I'm waiting for. I look up and see him striding across the floor and I'm at a loss for words.

"Mercy?" His smooth voice was deep and sexual. I stare into his eyes and blink.

"Oh, yes, I'm sorry, you're just so..."

His smile sliced across his face and he sat down.

"... intoxicating. I've never seen a man so breathtaking." I offer him my hand without a thought and my mind whirled as his smooth lips kissed my knuckles. We sat in the diner for a bit just talking before he asked if we should leave. I took his hand and stood.

"I would love to leave."

We got into his car, a tasteful BMW, and drove to my place. I invited him in taking his hand and guiding him upstairs to my bedroom. As I enter I hear the door click close behind me and I felt strong hands caress my shoulders and a shiver down my spine. His hands glide to my arms and I feel his lips on my neck. I turn and lay my hands on his chest, I feel his stiff nipples through the silk and I start unbuttoning his shirt. My breath hitches as one of his hands circles my neck as he kisses me on the lips. I arch my back as he presses against me, his cock hardening against my belly. I open his waistband and run my hand down his length, my other hand lingering on his naked chest. I pull away from his kiss and kneel, staring up at him and I pull his boxers away from his hips and his cock springs free. It's the first time seeing a cock that isn't mine and god, I need it in my mouth. I lick my lips as I open my mouth and take his shaft into my mouth. I slide my tongue along the underside and close my lips around his shaft, creating a little suction. I start pistoning my head around his cock, a little at a time until I feel his balls on my chin. I start to pick up a little speed and I feel his balls tighten.

"Wait" he breathed.

I stop, the tips of his shaft at the back of my mouth. I slide off him and look up into his eyes.

"What, was it something I did?"

"No," he replied lifting me to my feet. "It's just that I don't want to cum in your mouth the first time." He smiled as he pushed me back onto the bed.

"Fuck me," I said as I hit the mattress.

"That is the idea." He taunted as he lowered himself over me to kiss me. He lay on top of me, kissing me, our tongues lapping at each other and I felt a hand unsnap my bodysuit and pull my panties down, then that same hand gently slide along my own cock. He lifted himself off me, looking me in the eyes, I could drown in his dark green eyes but lost them as he spun me over to my belly, so I got on my hands and knees and arched my back, presenting my ass to him. I turned to see him squirting some lube on his bare cock before he positioned himself at my hole. I felt his tip at my ring and gasped as he pushed it inside me. I pushed back and dropped my head to the mattress as I moaned. I kept pushing back as he rocked into me, my face getting pushed into the mattress with each of his thrusts.

"Fuck me, Fuck me, oh my God."

I heard him chuckle as he picked up his pace and couldn't help but to keep moaning until he stopped, deep inside me and I felt his cock twitch and spasm as he shot his load, coating the walls of my ass with his cum. He collasped on top of me, his body pinning me to the bed, my own painfully rigid dick pressed between me and the bed, a painful reminder that I needed to cum too. I felt his softening cock slide from my ass as he rolled over and he fell asleep, in my bed. The least he could have done is give me a reach around for fuck's sake. As I stood to go to the bathroom, I felt something drip from my ass and run down my leg, wow, I didn't relize how much he had shot inside me. I ran a finger up my leg to my ass and stuck it in my mouth, the sweet and salty cum on my finger made me smile as I licked it off. My own cock twtiched painfully as I finished my walk to the bathroom and I stood over the toilet as I began to stroke my cock, as I thought back to what had just happened, I close my eyes and pick up the pace until I orgasm hard, thick ropes of cum stream from my tip into the toilet as I stifle a grunt. I look up and see myself in the mirror, my hair tausled and sticking to sweat on my face, makeup smudged, and a red mark from being pounded into the mattress, I smile, content; fuck, that was amazing, so much better than a dildo, next time I need to ride him so I can see my cock slap his belly and run my fingers through his chest hair as he penetrates me. I change into a lacy black negligee and lay down next to him hoping to wake up wrapped in his arms feeling his rock hard cock nestled in-between my ass cheeks ready for round two. When I woke up I was disappointed to find the pillow next to me empty and my house quiet. I rose and walked around looking for him to no avail. Shit, I was really looking forward to helping myself to some morning wood. Disappointed, I resigned myself to my rubber friend. I lubed it up and sat on it, closing my eyes as I rode it hard and fast imagining Chris between my legs, I felt my cock harden, my balls tighten, the tip of my cock hitting the floor, I started moaning and then, just as the dildo hit my prostate, I shot my load onto the floor and I slump, leaving it pierced in my asshole for a second before standing, leaving it stuck to the floor as I walk to take a shower. I got out and put on my masc clothes and cleaned up the mess I made on the floor. The semen was the most annoying as it had started drying, while I was scrubbing at my cum, I heard a ding from my phone.

Chris: I had fun last night, I'm sorry I had to leave early.

Me: I was disappointed, I was hoping for some playtime. I included a picture of the dildo and cum on the floor.

Me: I was able to make due.

Chris: Would you be willing to go out again? He hearted the picture.

Me: I would, what would we be doing?

Chris: What do you want to do?

My mind flicked to his chest, my hands against his pecs, his cock pistoning in and out, in and out, my hard dick slapping into his stomach, fuck his abs, his cock, his tongue, his hips driving up into me and I felt myself get hard again, my dick straining against the drawstring of my shorts, jesus I've never been this horny before. My phone dinged again.

Chris: Are you there?

Fuck, how long had I been daydreaming?

Me: Sorry, you mean besides you?

Chris: It sounds like you only like me for my body.

Me: I mean, it is a gorgeous body, the personality attached to it is great too.

We made a date for the following day. When he knocked, I answered the door in a lace cut-out body suit, my cock tucked, thigh high tights, the same fuck-me heels. If we made it past a greeting I could throw on a skirt and go out, but I hoped we'd get more then one session in. He stared at me, his mouth gaping and I could see his pants starting to tent. I smiled, that was the reaction I was looking for, before grabbing his collar and pulling him in for a kiss. As our tongues mingled I slid my free hand down his chest to his pants and cupped his junk. The longer we kissed the harder he got and the more I wanted him. I dragged him up to the bed room and pushed him onto the bed.

"My turn," I said grinning wickedly.

I crawled over his body until I was straddling his chest and I turned around so I could take off his pants but presenting my ass and cock to him. As I slid off his pants I felt his hands caress my ass cheeks, I stared at his hard cock and lowered my face onto it, sucking hard and pistoning my head. I felt a finger circle my ass and I moaned onto his dick, the vibration of my moan made him gasp and he bucked his hips driving his dick further into my mouth, I watched his balls tighten has I fellatioed him and I stopped as his breath got ragged. I turned myself around and tore off his shirt before lowering my sphincter down onto his shaft. I bottomed out, my cock hard, laying on his belly as I ran my fingers through his chest hair before lifting myself up and slowly lowering myself back down. As I lowered myself I felt my cock glide along his abs and I quickened my pace, as I moved faster my cock started to slap his belly and the sound of cock on abs, my moans, his moans turned my on even more.

"Fuck, oh God, you feel so good, fill me, fill me." I started screaming as his hips started to match my pace. I could feel sweat on my forehead and I looked down and saw him sweating just the same, his hands reached up and grasped my waist and started to use the extra leverage to fuck me harder and deeper.

"Oh shit, cum inside me, I want to feel you breed me." I whispered, out of breath from our pace and the feeling of his manhood stretching my ass and he slammed me down hard and his cock spasmed. A torrent of seed sprayed up into my intestines which in turn caused my own orgasm, my cum shot from my dick, a rope straight up the center of his chest and I gasped. I sat there, still impaled on his dick, panting, and quivering in the aftershock of our combined orgasm. When I caught my breath I rolled off his softening penis and onto the bed, I stared at the man who was so capable of making me cum and I smiled. I rolled off the bed and stood, I began to swing my hips as I walked to the bathroom and rotated, I raised my hand and signaled for him to follow me by beckoning with my index finger. I entered the bathroom, stripped off my teddy and started running the shower. As I leaned into the shower stall to test the water I felt hands on my hips and a cock nestled between my asscheeks.

"What are you doing to me?" He whispered in my ear.

"Seducing you, is it working?" I answered coyly as I stepped out of his reach and into the shower.

"I think it might be." He replied as he followed me in to the running water. The sight of his naked body, rivulets of waters running down his toned torso ignited my insides again and I felt my dick begin to harden again. I followed a droplet of water make it way down his body and onto his also hardening cock. I reached up to kiss him, our pulsating penises rubbing together between our bodies, we masturbated each other with our stomachs as we kissed under the water and we came again. This was so much better than the last time I thought.

"Do you have a friend who might be willing to join us?" I asked before my mind told me to keep my mouth shut.

"You mean a threesome?" He replied.

"Well, sure."

"Boy friend or girl friend?" Came the reply I wasn't expecting.

"Either, I typically only sleep with women when I'm not dressed, but I'd be up for it either way."

"I think I could work something out."

His answer sent butterflies to my stomach. I wasn't expecting him to go for it. But that's a story for another time.