Cumming on Mom

I couldn't wait for my mother's car to pull out of the driveway. She was headed for a three-day conference about 200 miles from here. I had just returned home for the summer after my junior year in college and was eager to relive some of the favorite masturbating sessions of my youth. They usually involved some form of crossdressing. Twenty minutes after my mother had left, I began to explore her walk-in closet and her dresser drawers.

As a 45-year old divorced professional woman, my mother's wardrobe and shoe selection were extensive. I soon found what I wanted. I took the silkiest pair of pantyhose I could find and put it on. My cock was beginning to get hard, but I was determined not to let this distract me just yet. Afterwards I looked at my mother's shoes and boots, and decided to try on a sexy pair of knee-high leather boots with three-inch stiletto heels. They were extremely tight but, after several tries, I was able to pull up the zippers on both boots.

I took a look in the full-length mirror that stood in one corner of my mother's bedroom and decided that I needed to find a tight skirt. From previous masturbating adventures I knew that my mother had a sexy knee-length leather skirt that barely fit me. I eventually found it again. I stepped into the skirt and pulled it up to my waist. However, I must have gained a few pounds in college because it took me awhile to pull up the zipper. But the leather skirt was very tight and looked fabulous.

Again, I looked at myself in the full-length mirror. By now my cock was crying out for some serious attention. I rubbed it slowly for about a minute, but I had other items belonging to my mother to retrieve. Among them was a pair of sandals with four-inch heels. My cock knew them all too well because I had fucked the toe holes – large enough to accommodate my cock - numerous times. I also put on a pair of my mother's leather gloves because my cock loves the feel of cold leather.

I attached one of the sandals to the post of my mother's bed. The other I held in my right hand for future use. I pulled up the leather skirt, lowered the pantyhose, and inserted my cock into the toe hole of the sandal on the bedpost. The feeling was fabulous as my pre-cum lubricated the bottom of the sandal, allowing my cock to slide back and forth easily. I lubricated the heel of the other sandal with my saliva and inserted it carefully into my asshole. The feeling of having my anus penetrated almost made me cum, but I didn't want to just yet.

I withdrew my cock from the sandal and decided to lie on the carpet in front of my mother's bed. I brought my knees and feet over my shoulders so that my cock was directly over my face. Having found the right position, I opened my mouth as a target for my cock. After a few more strokes, my cum shot out of my cock's head, hitting me in the face and landing on my tongue. I swallowed my own cum and straightened out on the carpet after my lengthy masturbating session. The boots and the leather skirt were beginning to hurt and I slowly took them off. Afterwards I headed for the shower to clean up my cock and my face. At the time, I thought I heard a car door slam, but I felt secure in the knowledge that my mother had left over an hour ago.

A couple of days later, my mother returned from her conference and asked me to help her carry her work-related materials and several department store bags up to her bedroom. I did as I had been told. Once inside her bedroom, my mother told me that she had returned to the house three days earlier because she had forgotten her cell phone. I was beginning to fear the worst. My mother continued to tell me that she had walked upstairs, seen me fuck her sandal, and making myself cum in my mouth. While I was dying from embarrassment, my mother assured me that she did not object to anything she had seen. Masturbation, she said, is healthy.

She then pulled a fantastic leather mini-skirt out of one of the bags and told me to put it on. She had seen me struggle with her skirt and decided that I needed my own. The skirt fit perfectly. She also produced a pair of red knee-high patent boots with 4-inch heels. The fit was still tight, but they were clearly several sizes bigger than my mother's boots. By now my cock was rock-hard. My mother told me that I could masturbate if I wanted to and should not feel ashamed. I pulled my cock out from under the leather mini-skirt and began to stroke it slowly and deliberately. After a few minutes I realized that I was close to cumming.

Throwing all caution to the wind, I asked my mother if I could cum on her tits. With a smile and without hesitation she opened her white blouse and pulled two beautiful, medium-sized breasts from her bra. She held them up and pushed them in my direction. I came almost immediately, covering my mother's boobs with my hot cum. To clean up the mess I had made, I licked my cum off both tits. "That's horny," she said and made her breasts disappear into her bra. "Now let's have dinner."