Momma’s Boy Finds His Woman.

This morning, I had been on Live Cam watching a 25-year-old man with an enormous cock who gently stroked himself while receiving encouragement from at least 20 people. I went through the list of watchers and found the usual suspects. There were a few quiet Eastern Europeans, a couple of a teenage men comparing while trying out their gear, two women, suspiciously young with nothing on their profiles - and at three older men.

I'm always compelled to comment on the Live Cam men and their penises and occasionally I get a private message. "Hi," usually starts the conversation followed by an invitation for some camera-to-camera chat at which time my heart begins to race as I reach for my cam and a beer.

Within minutes, I was enjoying a video chat with a very well endowed man from Milwaukee. He was younger than me, as are many nowadays and his erection was enviable. He had been pretty aggressive about getting together and this alone intrigued me. For about 20 minutes, I massaged my malleable cock, sometimes getting hard but mostly just enjoy the feeling, while trying to type short encouraging comments without obstructing the camera.

I didn't come, and I usually don't because I like the idea that I can go back into Live Cam and find another companion. My friend from Wisconsin on the other hand, stroked himself to a lovely, very liquid orgasm. When it seemed to be over, we thanked each other and offered to do it again another day.

It was while I was back in the Live Cam room that I received a remarkable private message, my first from a woman. She jumped right into it, asking questions about my age, my sexual peculiarities and interestingly, things on my profile page. I was taken aback when she asked me if I was a momma's boy. Was she implying that I was a closet homosexual because I masturbated with men online? She explained that she’d read my stories and posts and wondered, if my interests there, meant I was a momma’s boy.

I questioned her more but before I could get any answers she was asking if I wanted to video chat.

An offer like this is rare indeed so my camera was soon showing my jeans, behind which, I prayed, was an interested penis. Seconds later, in the small square above mine, I was seeing flowers. She was wearing a housecoat and the pattern was filling the screen with red flowers, green leaves on a silken yellow background.

"First time with a woman?" she said. I admitted to this and also that I didn’t quite know what to do. "Why don't you pull down your pants and show your cock. Isn't that what you do here?" I obliged, my heart beating even more loudly than usual. When centred in the cam, I tugged at my shy penis to give it a semblance of life and vitality.

"Shy around women, is he?" She said stating the obvious. At which, I tried to calm down, centre myself with the task at hand. I wrapped my hand around my penis, virtually enveloping it and began to massage slowly. "That's a good start," she said " Maybe you should pretend I'm your mummy." Then the red flowers and green leaves moved aside to show the curve of a perfectly rounded breast. I could feel something growing inside my hand and I typed - with my left hand, "Okay."

"You obviously enjoy breasts, I can see that from here. Want to see more? Is that what a mommy does?" The curved breast on my little screen became the pink brownness of an erect nipple. "Does mommy’s boy like my nipple? You're becoming very excited, or at least, more than a number of men I've met - of your age.”

“Oops! Shouldn't have said that. Really, it's a good cock." For this moment of embarrassment, I was rewarded with the camera zooming back to reveal the other breast.

Much to my enjoyment and amazement, I was now stroking a substantially erect cock. My heart was beating quickly and there was even drop of precum on my cockhead - that was turning a beautiful fleshy shade of purple.

My companion was not going to reveal herself fully. Nor would I. There was something special about this secret time which was being made even more special, because she had insinuated herself into my fantasies. I had not been open to this level of trust, which had likely reserved for my mother. Sometimes, I’d get close. In those short moments, chatting and jerking off with older men, circumscribed by our pure, that is, orgasm-focused relationships, I’d feel kinship. Here I was with a woman and it was the same, but different.

"Do you remember your mother's tits? Were they as round and full as these? You realize that these are a younger woman's breasts, don't you?"

She's right again, I thought. If I had any memory of my mother's breasts, they were replaced by these round, firm available breasts - sadly on a little square on my computer. My heartbeat had settled down but I was still excited, filled with a euphoria from my head to my cock.

Her cam drew back further revealing smooth white skin interrupted by a belly button. She had drawn up her legs so that I saw the smooth trim ankles and her pleasantly curved calves. "You enjoy my legs too. Your cock is twitching. I appreciate that kind of - appreciation." she said.

Again, she was correct. Her legs were very appealing, erotic, arranged over her waist revealing just a hint of bum. That's right - bum. Because it’s round and all her curves were well rounded, flowing together like a smooth road between breasts to belly, to thighs and calves to ankles. Momma's boy was on a road-trip.

"Going somewhere big fella? Maybe you should come somewhere instead."

Flattery will get us both everywhere and in fact, I was, if not big, adequately engorged to restore my faith that my hands had not simply grown too large for my cock.

Are erotic thoughts of a mom, a fountain of youth? There's something for future enquiry.

Her legs were moving sensuously, stretching and curling showing those curves in action and flashing a bit of pubic hair. And then - the big REVEAL.

"You're doing very well and I know you pride yourself on being able to stroke that cock all day, watching other men come, but now it's your turn." And with this she spread her legs and zoomed the cam, presenting a perfect delta of tangled dark hair. "Not every momma's boy gets this far. Men joke about wanting to get back into the place where they came from but that's just macho crap. Momma's boys love breasts and milk but a pussy frightens them. Are you frightened?

This woman in the little square on my computer was very good. She pushed buttons I thought I'd hidden away. As she spread her legs and opened her pussy, my cock jumped, sending me back to my thirties - so much pinkness, wetness and warmth. Then I was in my twenties, hard and erect, my cock banging against my belly. Okay, not really that far but the thought was there. My hand on my cock remained slow and firm but I could feel something strong and powerful rising from my loins, from whence had come so much early pleasure and apparently, would come some more - soon.

"Enjoy this! This isn't about me. It's about you and your urge to come and feel all that pleasure. Stroke! - a bit faster. I'm not going away." And with that she opened her vagina. I saw a raggedly round darkness that wasn't frightening. Instantly, my arse was sucked in as my penis leapt forth with the first of exactly three spurts of cum, all strong and all now flowing down my hand to my belly.

"Seems we've come a long way, you and I." And with that, her little square disappeared. I was alone on the screen, represented by a limp cum-drenched dick.

She hadn't gone…just her video. Her note said, "You're all momma's boys. Don’t grow up too fast." This was followed by a second note - a happy face.

87% (11/2)
Categories: MasturbationMature
Posted by smallfurrycreature
1 year ago    Views: 1,222
Comments (9)
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1 month ago
interesting. wouldn't it be exciting if she said she lived in your town?
11 months ago
I do not speak English language and writing traslator use.
I lose the details but I understand that it is an online chat with a woman who takes on the role of mom with her son (◦'⌣'◦)
Thank you very much this morbid and spicy story.
Best regards from Spain.
11 months ago
1 year ago
What a beautifully written encounter ... I really enjoyed it xxx
1 year ago
Wow now thats was a Hot Cam !!
1 year ago
enjoyed very much
1 year ago
Very nice job with this story, I loved how honest it was, Most guys I've talked with just don't understand what a good mama's boy is. The both of you really got it. Hope you keep up the writting you do a great job. Thanks
1 year ago
Your story is lean with just the right amount of texture to move it along. Bad stories go overboard on the sex, a good story always ends with the reader wanting more, well done!
1 year ago