My Secret Relationship Part 4

J and I just tried anal sex for the first time. It hurt like hell but I liked it enough to want to try again.

I told J that I wanted to wait a while until we tried anal sex again. He agreed that we should do it safely and as pain free as possible. That came as a big relief.

The next day I had the entire house to myself. When my mom left for work, I was in her room snooping through her drawers before she had even pulled out of the driveway. At this point there wasn’t anything I hadn’t seen already. Usually the first thing I looked for was to see if her dildo was in a different place. If it had moved, maybe she used it. The thought of my mother masturbating made me incredibly hard.

Sure enough, her dildo had been moved. It was now pointed the opposite direction from last time I had seen it. I pulled it out and held it in my hand. Sniffed it but didn’t notice anything but it’s normal smell. Licked it and then put it in my mouth. Tasted normal as well. Not that I needed it but the fee of that 10” dildo in my mouth turned me on even more. I couldn’t resist anymore or think straight so I jacked off while sucking that dildo.

A little more clear headed now, I continued to snoop around. Eventually I pulled out the box of old underwear and lingerie that was now too small for mom. I put on a pair of her nylons and a black lace and mesh babydoll. I added a pair of cotton panties and just laid in her bed. For some reason I decided to look in the drawer next to the bed and saw a magazine I had never noticed before. For the life of me I can’t remember what it was called but it was clearly about sex. I laid in her bed and skimmed through the magazine until I came to a section where readers would write in questions and experts would answer them. One of them was from an older woman in her 40’s whose husband wanted to try anal sex. I read the entire thing and suddenly I was motivated!

I instantly grabbed my mom’s vibrator which was a little smaller than the 10” dildo. This was much more like J’s penis in the 7-8” range. Mom had some KY in the drawer that I grabbed as well which the magazine suggested. J and I had just used saliva and that didn’t go well. The woman expert also recommended a position that was the most comfortable and she had mentioned that doggy style was easiest for her. Fortunately both of mom’s toys had suction cups on them.

The first thing I did was put some lube on my middle finger and I gently slid it in my ass. It felt really good! A few seconds later I slid a second finger in. With my free hand I began to rub my cock. I could feel my sphincter starting to relax a bit. I stuck the 8” vibrator to the wall and got into a doggy style position in front of it. I slowly backed my ass up until it was touching my eager hole. Then I began to push back. Little by little the vibrator went in. I remembered reading that pushing out like you’re pooping can make it go in easier so I did and then the head of the vibrator slipped inside my ass. I let out a gasp and bit my lower lip. It was a bit uncomfortable but felt 10 times better than when J and I tried.

Slowly I started to push back and forth allowing the vibrator to slide in and out of me. Then I decided to turn on the vibration. Wow! As soon as it started vibrating I started moaning uncontrollably. I was being very loud!

Now I was used to it and I began backing further down and deeper into my hole it went. Every time going deeper until it was all the way inside me. I started twerking my ass harder and faster. I was screaming into a pillow to avoid the neighbors hearing me. I had no interest in stopping. It felt so good! All I could think about was J. I pictured his strong hands grabbing my hips. His balls slapping against me as he drove his cock deeper and deeper inside me. His manly patch of chest hair glistening from the sweat. The primal grunts he’d make!

Then just as I thought about J pumping my ass full of semen, I grabbed my cock and stroked it as hard as I could. I shot cum all over my moms bed in less than 5 seconds!

After frantically cleaning up my mess as best I could, I put mom’s toys away, but I grabbed the box of clothes and brought it to my room. There’s no way she’d notice that a box of buried old underwear and lingerie was missing. This was to be my cross dressing starter kit.

I spent the rest of the week repeating the exact same thing every time my mom left for work. I was counting the hours until the weekend hoping J would want to get together. When he called and I answered, I heard his voice and I got instant butterflies in my stomach. My heart was pounding so hard I thought he’d hear it over the phone. When he asked if I wanted to come over that weekend, I excitedly yelled.

“Yes! Yes! Oh my god, yes!”

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