A Forgotten Fetish Rediscovered

Getting the head back inside me felt so good with all the new lube. It slid so easily past my hole now and I began rubbing and pinching my nipples to get an all over feeling of pleasure. I pulled back and let the head penetrate me over and over.

My slut clothes felt so good against my skin, especially now that I was being fucked by suck a lifelike toy. Each thrust made the dildo go deeper, and I felt it hit the bottom of my insides, deeper than anything had ever gone.

It hurt, but not enough to stop me from doing it over and over. I cried out "fuck me deeper, please fuck me deeper," and I tried to take even more cock inside me.

The pain was so intense, my own cock started to get soft. It still felt amazing to touch and precum was now constantly dripping out out of me. It was like my body decided to have a true anal experience. I reached for the bowl and put it underneath to catch my precum. As soon as there was enough, I licked it off the bowl so I could taste fresh semen in my mouth.

As the pleasure of fondling my soft penis got more intense the harder I forced the dildo inside me. I reached back and could feel it's balls were only an inch away from mine and I wanted to feel them touch me so badly.

My deepest regions started to ache intensely. I tried shifting up and down so the dildo could find its way further inside me. Arching my back, I found a position that let more of this huge toy penetrate me. It was like I was being split in two, and I called out loudly "You're so deep, Oh my god, it's so deep" almost pleading with myself not to go further.

My cock was completely soft now, but incredibly sensitive. I had never felt anything like this. The dildo was so filling, real cum to leaked out of me. Looking down the bowl it was covered in my pearl colored semen.

I continued to press for that last inch of cock. It ached inside as my body tried to adjust. I was getting tired, almost ready to give up when I relaxed a bit. Then I felt something new.

I must have found the tunnel that lead deeper inside me. The head of the dildo had punched its way its way through it. The rest of the dildo instantly slid inside me and the balls banged firmly against mine. I lowered my head and waited for the pressure inside me to subside before I could continue.

It hurt so much, but I was so turned on by being such a whore I didn't care. I started drilling myself with every inch of the dildo, loudly calling out "fuck me harder, fuck me harder".

I squeezed my balls hard, while frantically rubbing my cock to overcome the discomfort of being used like a silicone fuck doll. Then without any warning it started.

My legs began to shake uncontrollably, and I felt a massive wave of pleasure wash over me from deep in my ass. Cum leaked out of me like a fountain, but it didn't shoot, it just flowed like a tap, filling the bowl under me.

My balls ached as they emptied and it was hard to breathe. Wave 2 hit, and the force of the spasm pushed the dildo out of my ass with its intensity. My body shook all over and I cried out "Oh my god, its just Fucking perfect."

The last wave was much gentler, but the spasm was strong enough to push some warm liquid shortening out of me onto the towel. I thought that's what cum feels when a man breeds you. I fell forward on the bed, unable to move or think as the last of the twitches left my body.

I needed a moment to lie there silently and try to understand what had happened to me. It was at least 15 minutes before I decided to move. I was exhausted.

More warm liquified shortening leaked from my aching anus. I also felt an ache deep inside, where nothing had ever touched me before.

Looking in the mirror I was a mess, my wig was crooked. One stocking had fallen off my thigh, and the front of my Marilyn lingerie had cum on it. I smiled at the whore I became that night, and reached for the bowl of cum.

I watched in the mirror, as I held the edge of the bowl to my mouth and gently tipped it so I could drink it all. There was a lot of it, and I had to swallow 3 or 4 times. I enjoyed every drop, I had earned it. I turned my ass to the mirror and I was still gaping open, my anus bright red, and very raw from the pounding it had taken.

It was by far the most intense orgasm of my life. I couldn't wait to do it again in the coming weeks. I looked at myself in the mirror, and promised my new alter ego "Marilyn" that I would fuck her every time we had the house to ourselves.

My new goal is to hire an escort in the near future who offers strapon services, but I know I'm not gonna be satisfied until I get fucked by a real cock. Maybe I'll find a married crossdresser who likes to "play."

But those stories aren't written... yet

Love, M