Taking The Plunge

I'd been waiting for about twenty minutes before the doorbell rang. Earlier that evening I decided I would finally take the plunge and so I rang a local escort agency to arrange for a transsexual visit. This has been a secret fantasy of mine for a long time that I wanted to turn into a reality, but was too afraid to do so. However, as I was currently single and living alone, I thought... why not?

I remembered my first visit to a porn shop when I was a teenager, where I discovered some transsexual magazines in a section at the back of the store. There was something incredibly erotic about the thought of fucking a girl who could fuck you back. I was never caught up on the whole, "Am I gay?" thing that some people seem to subscribe to. I've never found men attractive nor had a desire to have sex with one. A transsexual just happens to be a girl with something extra.

The ring of the bell startled me out of my train of thought and I went to answer the door.

I opened it to a tall, busty, blonde, wearing a black dress, covered by an overcoat. Her dress was split to the thigh, revealing a set of long, slim legs. Her bust was spilling over top of her neckline.

"Hi, I'm Carol," she said.

I nervously introduced myself and ushered her inside. She looked over my shoulder into the bedroom and then asked if she could use the bathroom.

"Sure," I said and pointed her down to the end of the hall.

"You go sit down love and I'll be right there."

I stepped into my room, sat down on the edge of the bed and waited nervously. When she returned, she stood in the doorway and removed her overcoat. Underneath she had on, a black g-string and push up bra. Her breasts spilled over the top and you could see her nipples poking out over the lace edge.

"Are you nervous?" she asked.

"Yes," I replied.

"Good, you should be," she said with a smile.

Carol leaned forward thrusting her breasts into my face. I took her invitation happily and buried my head between them. They were nice and soft, and obviously natural. As I ran my hands over her breasts, I found her nipples and hungrily worked them with my tongue.

As one hand ruffled my hair, the other slid down to my cock and balls. She rubbed my hardness through my pants, but then stepped back from me.

"Now, let's get those pants off," she said.

I slid them down and as I did, my erect cock sprang out. I had been hard most of the day in anticipation of tonight and there was some precum already showing.

"Mmm.. nice," she commented.

With that, she leaned over and took my cock in her mouth. She licked the head of it and her warm, tongue raced over and around my shaft like no girls had ever before. Her tongue worked wonders over my dick and around my balls, but after a few minutes I had to ask her to stop, as I was on the verge of cumming.

"Hmmm," she said and looked at me. "Maybe we need to take your mind off your cock. This should do it."

With that, she stood up and peeled her g-string down and off. A nice shaped cock, bigger than mine, stood up in front of me.

"Suck it for me," she said and guided it towards my mouth.

I opened up and took her cock past my lips. I licked the tip and then the shaft before sliding my mouth up and down her length. She must have liked what I was doing as, after about a minute of this, she grabbed my hair and started fucking my mouth. As she thrust into my mouth, I could taste her salty precum. She pulled her cock out of my mouth and rubbed it across my lips.

"Your first time is it?" she asked.

I nodded yes, as I was too nervous to talk.

"Well how about you lay back for me honey and I'll make you feel good?" she said softly.

I lay back on the bed.

She reached forward, grabbed my ankles and, spreading them wide, pushed them back towards my shoulders. She reached over for the lube in her bag and, squeezing some into her hand, spread it over her cock. She leaned forward and moved her cock towards my exposed hole. She held me steady with one hand as she guided her cock to me with the other.

"This might hurt a bit love, so just try and relax ok?" She spoke soothingly.

She pressed the tip against my asshole and pushed forward. I felt it stop, before it found my hole and then with a further push, the head of her cock slipped inside.

"Ugh," I grunted as the initial pain hit.

"Hmmm," she said. "Let's go slow and try some more eh? Just relax and you'll be ok."

She pushed forward some more and her cock eased in deeper. My ass hurt a bit, but nothing bad now. With the aid of a few extra squirts of lube, she worked her cock in slowly until, inch by inch, she was buried inside me. She then started fucking me with deep, slow strokes; which felt amazing. She shifted her weight, up, down and sideways, stretching my asshole wider with each thrust. Soon, she was thrusting deeper and I could feel her pressing up against my prostate, which made my cock spring up as hard as it ever has. My hand made my way to my cock and I started stroking the shaft in slow movements.

"Oh honey, that looks so nice. Stroke that cock for me."

And with that, she reached down to fondle my balls. I could only take a minute or two of this before I blew my load over my belly. She reached down and rubbed the cum across my belly and chest, before placing her fingers in my mouth for me to lick clean. She continued to slowly slide her cock in and out of my ass, but after a few minutes of this she moved back and I felt her cock slip out of my ass.

"Will you turn over and lie face down please honey?" she asked.

I did as she asked and spread my legs wide.

"Now it's my turn," she said.

She pinned my legs down with hers, holding them apart and I felt her probing for my asshole. When she found it, she pushed her cock in deep with one stroke. I gasped as she stretched me wide.

"Ahhhh," she sighed.

After a few strokes, she started fucking me fast and hard, slamming her cock in and out of me, her balls slapping against me as she went. She would pull out every few strokes and I could feel my asshole staying stretched open. It felt strange as the air rushed in, only to let out obscene farting noises when she plunged her cock back in to fill me again.

She increased the pace and used the full length of her cock from tip to base, to work my hole. I could hear the squelching noises as she pumped my ass hard. I reached back to hold her arms as she fucked me without mercy. I was writhing under her as her cock continually plunged into my ass. My hole had stopped stinging now and I just felt full with each thrust. I was drenched in sweat as she pushed me down hard into the mattress with each thrust.

"Oh yeah," she kept repeating as she fucked me hard, her balls slapping against mine.

Finally, she groaned loudly, pressed hard against me and I felt her shudder repeatedly as the warmth of her cum filled my bowels. She stopped and let out a sigh. As she slid her cock out of me, a stream of cum followed, running down onto my balls.

I looked over my shoulder and she stood there, with her magnificent tits out, wiping her cock off with a towel.

"Now get dressed," she said. "I'll be back here tomorrow night at eight. I have something special in mind for you and this time it's free."

With that, she slipped on her overcoat and waltzed out my front door.

My cock immediately stiffened as I wondered what she had in store.