My journey into Hedonsitc crossdressing, Part 2

My mind was spinning. I'd spend the last 10 minutes or so sucking my first cock. Now, I'm being told to prepare myself for taking my first cock inside me. Do I want to get fucked? The reality of what was happening was almost too much to handle. Vince had guided me back into the bedroom, spun me around and helped me out of my dress. I slipped off my briefs (finally!) and my cock had been oozing precum.

I was highly intimidated now...standing completely nude, in front of Vince, who was also nude. Vince seemed to sense this and began telling me that he looked at me as very feminine, even when not dressed he saw me as I wanted to be viewed, and it would always be so with him. He had led me back into the bathroom, turned on the shower, and when the temperature was suitable, guided me into the shower and stepped in behind me. His cock was hard again, and he stepped in behind me a let his cock rest against my ass.
I was so incredibly aroused and wanted him to just **** me right there!

He reached around me...pressing the tip of his cock into the folds of my soft, smooth round ass. He grabbed the enema bag hanging from the shower and filled it with warm water. His cock rubbing up against me was driving me nuts, I was dying for him to push himself into me. He pulled back and inserted the nipple on the end of the hose, attached to the bag gently inside me, then squeezed the warm water up inside of me. He was instructing me to "hold my water" until he told me to release it.

I stood, almost frozen, as his hands were exploring my body, caressing my swollen cock, rubbing all over my ass, telling me how beautiful I am and how thrilled he is to have me with him. How much he is looking forward to "deflowering" me. He instructed me to turn and squat above the drain and let myself relax and empty the water. At first I was very embarrassed, and extremely uncomfortable having Vince witness what was happening. But, with his reassurance, I became much more at ease and we repeated this process until I rinsed completely clean.

Stepping out of the shower, we both dried off, and Vince e****ted me to the walk in closet. He picked out a dress and asked me if I would do him the honor of wearing this particular dress. It was like an evening dress, just to the knees, but with a full skirt, short sleeves, fully lined, a deep red with a back zip and a rounded neckline. I said certainly and took the hanger from him. Slipped the dress off the hanger, pulled in over my head, smoothed it out over my hips and ass. Vince spun me and did the honors of zipping me up into it. The torso was a tad loose, but the hips and butt fit like a glove, and the way the skirt fell about my thighs felt devine.

Vince pulled me out to the bed, and positioned me face down in a lying position. His hands slid up under the skirt and began massaging my ass. He'd let his fingers trace down the crack of my ass, lingering at my loosened hole, swirling a finger in a circular motion and inserting just the tip of a finger before moving on. He climbed up behind me, lifted the back of my skirt up over my hips, and then leant forward and began to rim me with his tongue.

This made me quiver and practically squirm. Never had I experienced this and it was intensely arousing. That, and knowing he was prepping me to take his thick, hard cock all up inside of me. My own precum was flowing freely at this point, and running all over the front of the dress. I had become so concerned about staining the dress, that I started to rise up and explain to Vince that I would ruin the dress...and he quickly assured me not to worry...he wanted me to stain it! With that, I laid back down and let Vince make me squirm, squeal and moan with delight.

I don't know how long he gave me a rim job for...15 minutes maybe. I wanted him inside of me so bad, but couldn't bring myslef to say it. I'm sure it was obvious to him, and he was deliberatly tantalizing me. He knew all too well what he was doing...and what the end result would be.

He rose up from ass, positioned himself over me so his cock was above my ass. He leaned forward enough to ease the head of his engorged cock into my tight little rosebud. I immediately responded with a fairly loud "Yessss", ohhhhh..... he withdrew the head and then pushed back into me, a little bit deeper, sending waves of the most pleasurable, erotic sensation I think I'd ever experienced. He continued to repeat this motion, each time working his thick cock deeper inside of me. Each thrust, I reacted more intensely to this intrusion deep inside my ass. I instinctively began meeting his thrusts, taking more of his cock until I could feel his groin pressed tightly against my ass cheeks.

I was being fucked...and it was the biggest turn on I'd ever experienced, I LOVED having Vince's thick cock inside of me. And it was obvious, Vince was enjoying me. I could feel that thick cock of his literally throbbing in my ass, his sweat beginning to seep into the back of my dress as he continued his onslaught.

He began to whisper things into my ear as he began to fuck me with harder, more impassioned thrusts. Telling me what a hot, incredible ass I have, and how much he loves the feel of his hard cock inside "HIS", hot little sissy. How I'm his little sissy bitch now, and how I'll crave to be taken by his cock.

All I could do was moan softly in response. I began to feel an orgasm welling up inside of me. I was trying to hold back, but I couldn't control myself. I blurted that I was going to cum...and then it happened. Vince began pumping my ass really hard...his cock thundering up inside me, MAKING me cum...MAKING me spew all over myself, the dress, the bed. This older, overweight, balding man had literally, fucked me to orgasm! As my climax began to subside, Vince suddenly slammed deep inside me, gripped my shoulders incredibly tight, and began to explode, spewing bolt after bolt of his hot cum deep into my abdomen. His body, quaked, bucked and spasmed as he filled me with his very essence. Heavy on top of me, his orgasm subsiding, I'd never felt like this before, ever. We lay together for several minutes, all the while I could feel Vince's cock quiver and pulse inside me. So amazing hot and erotic, and soaked in my cum in the front, full of Vince's cum in my ass!

As Vince's cock began to soften, he slipped it out, and without warning, climbed off of me and pulled up so his cock was near my head. He spun me onto my back, and literally pushed his cock to my lips, held the back of my head, and told me to clean his cock suck him clean. I was a bit repulsed at first, but got past that and did what he asked, tasting both of us on his cock.

This was the first fuck in a long weekend of what would prove to be quite a "coming out party" for me. Vince would make me take a name...which is where Elaine came from. I'd never enjoyed sex this intense...but this was just a glimpse of what was to come for me....
100% (30/0)
Categories: AnalGay MaleShemales
Posted by elainetgrl
3 years ago    Views: 749
Comments (9)
Reply for:
Reply text
Please login or register to post comments.
1 year ago
Mmmm so hot !
You never forget your first fuck
2 years ago
Daddy can't wait to breed this slut
3 years ago
The first fuck is always the best when done right
3 years ago
What a hot and desireable first experience. Very, very sexy!
3 years ago
Well written and very hot
3 years ago
That was fine wopuld love tobe fucked like that
3 years ago
very nice
3 years ago
Nothing can top that 1st time. Good story.
3 years ago
really good stuff Elaine!