A Mom and Crossdressing Son Fantasy

The story is about how my passion for wearing women's lingerie helped me to establish a more intimate relationship with my mother.

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I'm a 42-year-old man and I still live at home with my mother. My Father passed away 20 years ago. We live in a suburban bungalow and I have a nice little apartment in the basement. It's not as private as I would like. That's important because four years ago after discovering a number of chat sites where men present themselves in women's underwear, I began to become interested myself. Now, once a month, I dress in very fine sheer black stay up stockings, lace panties and a bustier with cups small enough to fit me. I had thought of getting high heels but it was almost impossible to fit my size 13 feet.

My mother is 62 years old and still quite attractive for that or any age. She's slender and her breasts are nicely large but not ridiculously so. apart from the fact that she drops into my little apartment regularly and without warning, our relationship in the tiny house is very good. One night recently, that changed dramatically and I would say, for the better.

Mom was going Out of town for three days to see a friend providing me with a good opportunity to go a little crazy, dress up, drink some fine wine and maybe toke a bit. An hour or so after she left the house I started my ritual, bringing out my underwear and choosing the set I wanted to put on. I had chilled some wine and found my stash.

I would then go to one of the camrooms where men would masturbate together and some of those men would be in women's underwear. I started broadcasting sure that I would get compliments for my underwear but also for my hardening cock that would eventually burst from the tiny panties. My real goal though was to be asked to Skype with someone who was also online and on cam so that I could check out his goods. Most often, he would cum and I would go back to the chat rooms to show myself off again. I'd do this about two or three times and then I finally (I hoped) find somebody I would cum with.

I had done my first show and skyped with a large man in little girl underwear with a thick uncut cock who came beautifully. Then I returned to the camroom. The sound was on so I didn't hear the door open behind me. What I soon noticed was the reflection of my mother standing in the doorway a look of shock on her face. I covered myself and spun around to face her. "Mom, I am so sorry. You shouldn't be seeing this. It won't happen again." I was so terrified that I could hardly get the words out.

My mother's expression of shock slowly changed to one of wonder. "This is a total surprise. Actually I shouldn't be surprised. You're old enough and I saw a pair of panties in your dresser drawer. Now it's all clear. Please don't worry. I suppose what you do is like a hobby, with benefits. "

"I can explain anything mom, and I'll stop right away. This is just fun and I'm sorry that you had to see it." I said all this while attempting to cover up my rapidly softening hardon. In the background a number of tabs were open with men in panties stroking themselves so my mother was shocked not just by me but by my audience of cocks.

"There has to be a way to make this normal for us." she said. "I've always thought our relationship was very open. This has obviously been a very closed part of your life that you've kept from me. I'd like that to change that right now."

"Turn back to your computer," she demanded "and return to your friends and carry on as if this hadn't happened. I'll be back in about 10 minutes." She turned and went upstairs leaving me only slightly relieved that she hadn't exploded in anger.

It wasn't easy to refocus. I had a bunch of hard cocks being masturbated in front of me. The vision of my mother coming into the room made me tremble, but after about five minutes I was able to divert myself with the cams. I was avoiding the inevitable when my mother came back into the room.

True to her word she was back in exactly 10 minutes. I kept facing the computer trying desperately to avoid turning around. Eventually I had to and it was my turn to be shocked.

Mom was wearing almost the same kind of undergarments as me except that she had perfect high heels on and the cups of her bustier were overflowing with her ample breasts. Her panties barely covered her hairy pussy and she wore a garter belt to hold up her sheer black stockings. She stood in the doorway striking a very sexy pose. My shock turned to arousal as my cock swelled in my own panties.

"I hope this puts us on equal footing", she said. "I'd hate for us to have secrets that we couldn't share. You might have wondered where was I was going on those trips out of town. In some cases it was to meet friends who enjoy it when I dress like this." And then she smiled seductively. "So how do you like it?" she said cupping a tit and pushing it up so that a very hard red nipple stuck out.

"I like it very much but I don't quite know what to do with this" I said surprised at how rational I had become. "I can have my perversions but they were private and now they're public or at least private between us. I'm still uncomfortable with this although I'm also very excited and I find that alarming. After all, you ARE my mother."

"Let me help you with that." she said and walked towards me. "I want you to stand up and let's put some more lights on so we can see how beautiful we look." We stood there, a strange mirror image of each other with one major difference - my cock was very hard, veins looking like they'd burst, the sticking out the side of my panties.

"And let me help you with that too." she said reaching down for my cock. She grasped it firmly in a warm hand and started to stroke. My legs became weak and I almost fell down. She put her arm around me and pulled me closer, putting my face into her bosom. "Let's sit down on your coach and get comfortable." she said. I stumbled and then tumbled onto the coach. She, on the other hand, moved gracefully swinging her hips with each step and making herself look even sexier. She sat beside me and gave me a moment to take in this fabulous view. Then she returned a hand to my painfully stiff cock.

"This is what we should be doing. Is that okay?" she asked. "Let's just relax and enjoy this. You're very beautiful and I'm turned on by you."

Her hand moved up and down my cock slowly then quickly then slowly in unpredictable yet astoundingly pleasurable ways. I was going quite crazy with the sensations and thought I would come at any moment. She pulled out the breast closest to me and placed a nipple in my mouth.

"Suck that like you did many years ago." she hissed. And I eagerly sucked gently chewing her hard nipple.

My mother stroked my cock so that I would become very excited yet I didn't come. As she stroked I would suck harder and then softer and I could have sworn I tasted milk but that was probably wishful thinking. It was at least 30 minutes before my cock and balls became uncontrollable. I moaned as I thrust my hips and sucked even more keenly. And I had the best orgasm I could remember. There was so much cum and it was oozing all over the front of my bustier.

"Son, that was lovely. I'm so pleased that we were adult enough to take this uncomfortable situation and turn it into something beautiful." she said getting up from the couch. "I really must be going now. I only came home because I'd forgotten my wallet." she giggled. "Before I go, let me tell you where you'll find my detergent for delicate fabrics. I know how hard it is to get cum out of lingerie. She stood elegantly. I was seeing her in a whole new light, sexier that I would ever have imagined her. She walked to the door closing it as she left, leaving me to the cocks on the computer who had become stiffer having seen the whole show.