Crossdressing boy

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Crossdressing boy

When I was 14, I was sick and off school for a month. Both my parents worked, so I was left at home alone.
I had seen porn mags and had learned to jerk off from a couple of friends at school. I loved it and would jerk off every time possible.
My mom left for work later than my dad and I saw her often in just panties and bra coming out of the bathroom before she would dress and leave or work. She was about 5'5", just a little chubby with big breasts and big nipples. I had noticed her hard nipples when she was in a bathing suit. My mom was often in my mind when I jerked off. Not only did I think of her but so did my friends, the ones that taught me to jerk off. We all had pics of our moms in bathing suits and when we got together we would put them on a coffee table, cover them with a piece of transparent plastic to protect them and jerk off on them. We would see who would cum the fastest and the most. We even licked off the cum pretending we were licking our moms clean after we fucked them. One time the rule was that the guy who came the last had to lick all of our cum alone off the pics. I lost on purpose just to taste their cum. They laughed as I licked but I did enjoy the taste.
One day she asked me if I could do the laundry to help out. Having little to do I said that I would. After she left, I went to start the laundry and noticed some skimpy panties and bra that I had never seen her wearing.
I picked them up and got a hard-on right away. They felt so nice in my hands that I rubbed myself with the, making me harder than ever. I jerked off into them with my biggest load ever.
Putting the laundry to start, I wondered if my mom had other nice underwear. So I went to my parents room and started looking in her drawers. Wow, I hit the jackpot, all sorts of nice things, even garters and nylons.
I started taking out and touching them, getting a new hardon.
I liked the feeling of them against me as I rubbed them on my chest.
I wondered what they would feel like if I put them on.
Quickly I went and showered and went back to that drawer.
I took out some nylons, garters, panties and top and started putting them on. I had some trouble but managed anyway. Wow was I hard. I jerked off another 2 times and had to wash her stuff before putting them back. I figured that the time I would be home sick would be more fun now.
This went on for the rest of the week, trying all her different lingerie, wondering how she looked in them and how it would be to fuck my mom. The weekend was a bummer because my parents were home.
Sunday night, my mom said that she had Monday and Tuesday off, my heart sank and I looked disappointed.
My mom asked me why I looked disappointed, wasn’t I happy that she would be home to take care of me, she said with a smile.
I smiled meekly back and said yes that it would be great.
Monday morning, I stayed in bed later. My mom came in my room and I was surprised that she was not dressed but just in a bathrobe. She said she had something to ask me, which worried me a little.
She sat on my bed and asked if I had been in her room the week before.
I stuttered that I didn't understand so she said that she noticed that her underwear were moved around everyday. I blushed and tried to hide, my mouth dry realizing that I was caught.
She put her hand on me and said it's ok, she didn't mind. My eyes widened. She asked what I did with them as she slowly undid her bathrobe, showing the lingerie she had under. Not looking at her, I muttered that I played with myself while touching them. Is that all you do she asked as she rubbed my hand. Some of my nylons seemed stretched.
Her next question was if I put them on. I swallowed hard and tried to answer but my mouth was too dry. What she said next floored me, She told me to go to her room and put on what I liked best, helping me get out of bed, I tried to hide my hardon as I passed by her. She slapped my ass and said to hurry.
My heart was beating so fast. Here was my mom wanting me to put her lingerie on. I put on some nylons and a garter, crotchless panties and a see-through top all in black. Slowly I went back to my room. My mom was lying on my bed in her lingerie, smiling at me as I walked in.
She told me that I looked cute and sexy especially with my hardon. She motioned me onto the bed and hugged me. I felt great. She let me grope her all over as she played with my cock. She made me lie back and kneeled between my legs and took my cock into her mouth as she fondled my balls. I came like never before, so fast and so much and she took it all in her mouth and then came up to kiss me and make me taste my cum. I wasn’t sure but figured what the hell and took it as I trusted my mom.
Seeing that my hardon had not subsided, my mom lay back and told me to fuck her.
This time I lasted longer. As I caught my breathe she told me that I had to make her cum with my mouth and told me how to eat her pussy. I was in heaven.
We did this on Tuesday again and in every room of the house. The rest of the week she would leave me her clothes to put on while she was in the bathroom and would let me fuck her before she went to work.
Friday after I fucked her she whispered “Wait til tomorrow. I told your dad about us and he wants in on our games” She kissed me and left for work. I jerked off at least 4 times that day wondering about the 3 of us

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