A Forgotten Fetish Rediscovered

My boyhood was exactly the same as everyone else's. That is assuming all young men at the age of 18 suddenly can't wait to have the house to themselves, so they can raid their moms closet for her pantyhose, slips, bras and panties. As long as it was feminine, and felt good against my hyperactive penis, I was a fan.

I especially loved pantyhose, they felt so good on my dick. I could cum from just walking around the house wearing them. Anything mom owned that was made of satin I wore, or used to jerk off with. Even her high heels and short silk dresses could make my dick hard whenever I wore them.

With everything imaginable in mom's closet creating a sensory overload for my cock, you would think I would leave my ass alone, but you would be wrong. It started with pens, but they were soon replaced by brush handles, and then my favorite, fancy glass perfume bottles. A couple of them got stuck inside me when I got carried away, but that's another story.

My need for anal play and crossdressing disappeared after I started getting real pussy on a regular basis. I would simply have my woman wear the stockings and heels. Sometimes they would dance around in satin lingerie for me. Then I would sink my now pleasantly big cock, deep inside every hole she offered.

I chased the desire for more intense orgasms most of my life. It was all about pleasure. That's who I wanted to be, straight as a ruler alpha male with a big cock. The crossdressing and anal acrobatics were left far behind.

All that changed 25 years later, during an innocent trip to a thrift store to look at some old records. For some reason this store always hung the women's stockings and pantyhose right beside the old record display. Every time I was there, I remembered how much I enjoyed wearing them when I was younger.

Like most mature couples, my wife and I didn't enjoy the kind of sex that included heels and stockings anymore. That disappeared like blow jobs and anal. It just seemed to fade away. I wasn't bitter about it, we had fucked 5,000 times and there wasn't anything new to try. I still loved her very much, but I was starting to miss the naughty fun I used to enjoy.

Eventually, I saw a pair of black XL stockings on the pantyhose rack, and decided to buy them. It was a bit awkward at check out, but I just remembered the clerk has no idea why I want them. My wife never wore stockings or lingerie anymore, so I needed to be brave and find my own if I wanted to experiment again.

The next time my wife was out of town, I decided to have a couple glasses of wine and wear my new stockings around the house. It felt sexy, slipping them out of the package and rolling them down to the toe so I could slip them on properly. They were the first pair of stockings I ever owned, and I bought all for myself.

I made sure they were straight on my toes, then I pulled each one on. As they rose up my leg, the sensation was immediate and my cock started getting hard. Looking down at my legs, I thought they looked so sexy, other than the hair on my thighs that is. If I was going to keep doing this I would need to fix that, but for now they felt and looked better than I imagined.

I was walking around my bedroom, enjoying the wine and the view in the mirror, when I spotted an empty perfume bottle in the waste basket. I picked it up and examined it. It was glass with a bubble pattern, similar to anal beads I'd seen on the internet, only these bubbles were all the same size.

Holding it in my hand I thought, "you have the whole place to yourself, why not fuck yourself like you used to."

I headed to the kitchen to see if we had any shortening. When I was young shortening was by far my fav lube. Some of mom's hand creams made my ass sting, or got in the tip of my cock. None of them really worked that well for anal, but shortening, it never let me down.

It didn't take long for me to find some, and I brought it back to the bedroom with me. After setting a towel on the bed, (I knew shortening made a mess) I sat down and smeared some on my now semi rigid cock. It felt so good after all these years to be doing something naughty, and not just rubbing one out to get a cheap release.

I started stroking my cock with my left hand, occasionally moving down to smear and squeeze my balls. My right hand was free to hold my wine glass, and I watched myself get harder as I drank my red wine and relaxed.

I was surprised how fast I felt a desire to cum. When I was younger I may have let myself go over the edge, but I was in no hurry tonight. I stopped stroking and let my fingers gently trace the veins around my head and shaft. I hadn't been this hard in a while and it felt good to let my fingers wander.

When my wine was finished, I picked up the perfume bottle and examined it closely. The first ball of the base was as thick as my cock, but it narrowed before the next ball of glass started. I was a bit scared to put any part of a bottle inside me again, but I was too horny to turn back now.

I took a healthy finger full of shortening and began smearing it on the bottle, being sure to cover the bottom half completely. I spread my stocking covered legs, and put the rest on the lips of my anus, gently pushing a little shortening inside me.

The feeling of touching my anus again was very pleasurable, and I ran my fingers around the opening, grinding on them like a slut wanting to be fucked. I brought the bottle between my cheeks, and began rubbing it across my opening. The cold glass felt good, and I started stroking my cock again with my free hand.

As the base of the perfume bottle passed by my anus, I gently pressed it a bit harder each time. I could feel my body yearning for me to push it inside.

After 10 minutes of teasing my ass, my cock was too hard to touch anymore and I let it rest against my stomach while I concentrated on getting the bottle inside me. I laid on the towel and lined the bottle up perfectly with my soft pink anus, slowly pressing it harder and harder. As the lips of that little hole parted, I felt the cold of the first ball as it stretched me open.

I also felt the familiar sting when my anus was pushed to it's limit. I took my cock in my hand again and stroked it so the pleasure would overcame the pain. I remembered that pretending to push something out, sometimes helped it go in. As soon as I tried pushing, I felt the first cold glass ball slide inside me.

It felt so good to have something in there again. I instinctively started grinding my prostate against the cold glass inside me. I felt precum flow down my shaft to the tip, and my body spasmed warmly. I let go of my cock and squeezed my balls hard to keep from cumming.

The feeling of being a bottle slut again turned me on more than I could imagine. I easily pushed the next glass ball inside me. There were 5 glass balls on this bottle and I told myself not to go past 3. The second ball pressed right on my prostate and it felt incredible. All the muscles inside me flexed wildly to grind against it, and I felt more pre cum dribble out of me.

With the bottle firmly in place, I let it go and used one hand to squeeze my balls, while I stroked my cock with the other. There was no turning back now, I felt my prostate load up. I was going to cum.

My legs began to shake, and I felt the whole body orgasm starting that only anal ever gave me. Looking in the mirror, I could see my nylon covered legs up in the air, and the bottle inside me. It was simply too much to resist and the first wave of pleasure washed over me.

I pressed my ass hard into the bed, and intentionally aimed my cock at my face just like I did when I was younger. The first ribbon of cum was thick and heavy. It shot out and landed on the pillow beside my head. The second ribbon landed on my neck and chin. I wished I had tilted my pelvis more to give myself a proper facial.

The pressure remained intense for the next few ribbons of cum that landed on my chest and stomach. I felt the deep leg shaking anal orgasm finish, and the last week spurts of cum dribble out on my thighs and onto the black lace of my stockings.

I stayed there for next 10 minutes, my chest heaving and my body twitching as the warm blood inside me cooled. The pleasing sensations slowly drifted away. I could still feel the bottle deep inside me and reached down to gently pull it out.

I couldn't resist pressing my ass into the bed when I was cumming. It forced the bottle deep inside me and always made the orgasm more intense. I loved the sensation of being fucked by those little bottles.

I was relieved to find one glass ball still on the of my outside my anus. I wiped my hand on the towel, grabbed the ball, and slowly pulled it out of me, enjoying every bump on the bottle as it exited.

I turned my head and the large spot of cum was on the pillow right beside my face. It was a beautiful pool of pearl. I couldn't resist sucking it off the pillow and into my mouth. I always liked the taste of my own cum and it had been way too long since I had enjoyed some.

The salty sweet taste was so familiar, and after I swallowed, the bitter taste that coated the back of my throat. Nothing tastes like fresh warm cum.

I felt like such a whore, all the things I loved about crossdressing and toys came rushing back, making me want to go even farther in my journey this time.

I got up and began the cleaning process, the towel, my body the bottle and the bed all needed attention.

I knew one thing for sure, I loved how toys and crossdressing made me feel. I promised myself to try and make the next experience to be even more intense, and I started to make plans for it.

The first step was deciding not to jerk off anymore. If I wanted to cum, I needed to dress up, and be fucked like a whore. I wanted intense orgasms, not the tiny jerk off in the shower ones.

Next, I needed new lingerie that felt and fit as good as it looked. I also needed to trim any hair off my legs I couldn't easily cover up.

Lastly, I needed a new toy that looked and felt just like a real cock. If I was going to be a whore, I needed to know how it felt when she was being fucked.

The first break came when I returned to the thrift store, and looked thru all the women's clothing. I found a large long sleeve crop top in skin color. Then, in the lingerie section, a long red spandex baby doll with black lace. Looking at the tag it said "Marilyn Monroe collection". I knew I would love wearing it.

The clerk at the store gave me a really funny look when I paid, but I stopped giving a shit what clerks think. I was enjoying my naughty shopping finds and the anticipation of wearing them.

The next bit of luck came on-line. I discovered my feet were larger than standard women's sizes, so I searched some drag queen sites. One of the sites had a "swap shop" section, with seller in my area that had Pleaser shoes she didn't like. I left her place with a stunning pair of black heels that you could strap to your ankle with real padlocks.

It took a few weeks before I got anything else. I found a wig, and some large, thick white stockings with frilly toppers in a Cosplay clearance bin. The wig was purple, long and very feminine. The stockings had a seam in the back that looked very erotic on the lady pictured on the package.

My last need was a lifelike cock. After checking several local sex stores, I headed to a huge warehouse store on the edge of town. I had never purchased a sex toy for myself, and the options were endless. Vibrators, beads, plugs, dildos, I wasn't sure what I wanted when I got in there.

After an hour of looking, and reading a million boxes it hit me. Just get the closest thing they have to a real mans cock, that's what a true whore would want.

Once I thought it, I knew it was right. The ultimate anal experience for anyone is having a real throbbing cock in your ass. I wanted to feel dominated, have a man empty his balls, and fill me with his seed. Anything I bought should be as close to that experience as possible.

It didn't take long before I found what I wanted, a thick 8 inch lifelike dildo with big balls and a large suction cup base.

I held it in my hand for a moment and admired the accuracy of the veins and pink skin. It was soft to the touch, but firm just like a real cock. The head was larger than the shaft so it would be hard to get it in, but I wanted that challenge. It measured 8 inches from the tip of the head to the balls that hung down and even swung a little.

The large suction cup base would hold it steady on the headboard or floor, and it was so large there was no way I could accidentally take it all. It was perfect for my next fantasy and I kissed it on the head before leaving the store with it.

With my new clothes and amazing dildo ready, I started looking forward to the next night by myself. I had been shaving my balls regularly, and slowly trimming the hair above my cock to look like a women's pussy.

Last week I shaved the tops of my legs, so they were hairless. My wife only commented once, and I told her I felt better and cleaner when I kept everything short. She never said anything about it again.

When the day finally came that I would have the house to myself, I was almost crazy with anticipation. It had been 8 weeks and my wife was staying out of town until the next evening. Getting home after work, I decided to slip on my new white stockings and high heels for a walk around the house before dinner.

The stockings looked so sexy with the seam going up the back, and the frilly white toppers. When I put them on, I felt my cock spasm, and when I slipped on the heels and locked the padlocks, I was hard. I stopped and admired my legs in the mirror a few times. Eventually deciding to skip dinner, and put on the rest of my lingerie.

I put the crop top on first, it covered the hair on my upper body perfectly. Its long sleeves and size were perfect for me. Then I slid on my spandex Marilyn lingerie. It was snug but felt so good against my skin, I pulled it down to cover my ass and my hard cock rubbed against it in the front. The sensation made me tingle with every step.

Lastly, I put on my wig. The hair felt so nice on my bare shoulders, very girly. Everything fit and felt great. I was almost afraid to look at myself in the mirror just in case I looked like a joke. I walked into the bedroom with its long mirror and stood there. It was better than expected.

I wasn't quite passible, but I looked slutty enough that I knew if it was me in the bedroom with her, I would fuck her hard. I opened a new bottle of wine and started to look at crossdresser porn on my computer.

My cock was constantly twitching now, and I watched several scenes where the crossdresser took a big cock inside her. I wanted to see how she would behave, and what made her cum the hardest.

I had finished my third glass of wine when I decided no more porn. I need a big cock inside me! It was time to become the slut I fantasized about becoming. I went to the bedroom and picked up my new toy. I told it "I can't wait for you to Fuck me" and stuck it the center of my king sized headboard.

I laid a fresh towel on the bed, I got the shortening out and got ready. I even had a large bowl to catch any cum that leaked out of me.

I dimmed the lights just a bit, laid down on the bed, and started to pretend their was a man with a big cock in my bedroom. He wanted to fuck me.

I began to stroke the dildo and talked out loud "I love how hard your cock is already, do you like it when I touch it?"

I slid my hand around head and down the shaft. I massaged the balls with my fingertips, "Oh my," I said "These feel very full, I hope my tight little anus can take everything you give me."

I leaned in and kissed the dildo. The roleplaying was so hot, I started touching my own balls. I was rubbing them in a circle with my fingers, pretending I had a wet pussy. I kissed and licked the dildo for a long time as I played. Eventually, I licked my lips and took the whole head in my mouth. It felt like it was real.

"Do you like it when I suck it?" I said, sliding off the head momentarily. It was a very taboo feeling to have a cock shaped object in my mouth. I was surprised how hard it made me, especially when I saw myself sucking it in the mirror.

After sucking it for while longer, and stroking it in my hand, I pulled of and said loudly "Fuck my mouth like you fuck a whore".

I opened my mouth more and took about 6 inches of dildo before it hit the back of my throat. I tried forcing the last 2 inches in, but I would gag when I did. I shoved my mouth down that cock over and over. It hurt, and it was hard to breathe.

I had a new appreciation for every woman who sucked my cock well. I was doing my best to ram it down my throat, but I needed more practice. I slid my mouth off the saliva covered dildo and kissed it again. "One day I'll take ALL of you in my throat" I said. The thought made me very horny.

I reached for the shortening, and started smearing it on the dildo. "Are you ready to take the cherry from my ass?" I asked it, as I stroked white lube over the head and shaft. I got on my knees and turned my ass toward the headboard, the dildo touching me between my ass cheeks.

The reflection in the mirror was amazing, my stockings and heels were so slutty, and I pulled up my lingerie in anticipation of being fucked. I leaned down with my shoulders resting on the bed and whispered, "now fuck me like a whore."

Hearing it out loud made me so turned on, I couldn't wait to be a dildo slut. I lubed up the lips of my anus, and slid the dildo up and down the crack of my wanting ass. It felt so good, I started to squeeze my balls with my free hand and prepared to be a fuck doll.

It was too intense to resist when the head of the dildo passed over my opening anymore, so I lined my little hole up with it. I was nervous, the head was much larger than any perfume bottle had fucked before. It would take some time to get this inside me, without it hurting so much that my pleasure would be lost.

I stroked my cock, and pressed my opening against the head of the dildo, feeling the pressure build against my tight little hole. Each time, more of the head would penetrate me, and I knew this would be much different than a little bottle. I pressed harder and harder, trying to get the head inside but I had to be patient so I didn't tear.

I added more shortening to the dildo, and gently but firmly kept pressing the head against my ass. A felt myself stretching more and more. The head was slowly going inside me. I was like a virgin taking her first cock.

I was determined to have this large toy violate me, so I started pressing as hard as I could stand. I stroked my cock while I did it to increase my pleasure, often looking in the mirror to watch myself lose my virginity.

I felt a "pop" when the head finally stretched my anus lips far enough to break through and get inside. It stung, I was stretched farther than anything I had taken before, every move I made was now a mix of pain and pleasure.

I stayed perfectly still, and let my body adjust to its new invader, saying out loud "Just give me a second to relax baby, then you can fuck me harder."

The pressure inside me was enormous and it hurt so much, I briefly considered stopping.

After a few deep breaths, and a serious effort to relax my anal muscles, I began to gently rock against this new huge toy inside me. The sharp pains were subsiding, and now it was more of a nice aching feeling.

It took a few minutes but I found a rhythm and angle that allowed me to start fucking myself. It was so new to feel something so big and firm yet soft inside me. I kept taking a bit more with each thrust.

I lubed up again, this time pressing lots of shortening inside me. It was much easier now that my anus was gaping open. I wanted to see how much of this amazing cock I could take.