A very odd set of circumstances left me growing up alone and 20, with my Mother, who was 37.
Dad had left her when I turned seven or eight ... I barely remember him any more. Mom was a schoolteacher, thankfully not at my school, and for a while we were doing pretty well.
Our apartment complex raised our monthly rent, so Mom had mentioned to me that she was going to find a second job.
Less than a week later, she was flush with cash, paying our rent and getting groceries — until the following month when the rent was due again. She had left for an evening job of some kind and again she was loaded with cash, this time giving me some, paying the rent and getting some groceries.
This happened about three more times, with Mom always coming up with money, which I never questioned. It was summertime, so I was out of school and she worked a part time summer school shift.
Some older guys came by the house asking if my Mom was 'working' tonight, and I mentioned I thought so — I asked if they'd take me to her because I had never seen her 'work' before. I honestly didn't know what they were talking about, but I was a little bit bored.
They took me to a dive place called Miss Kitty's — they told me to give the guy at the door a twenty to get in, so I did.
The place smelled of cigarettes and alcohol, neither of which I had been around much, Mom occasionally smoked.
A faceless voice said, "And Now Gentlemen, Welcome to the stage Miss Sunny Deelite!"
Recognizing the music from the movie Gypsy, I heard 'Let Me Entertain You' begin and a beautiful woman came onstage and started to dance a little and really bump and grind. It was getting me hard and all she was doing was moving around on stage, bending over and showing off a nice pair of tits.
I hadn't seen Mom yet, thinking she must be serving drinks. She's told me she'd been a waitress in a bar when she was younger. This was probably how she was making all of the extra money.
My eyes gravitated back up to the stage as 'Sunny' had taken off her top showing off a real beautiful pair of tits. She had started to play with them as she danced, actually licking her own nipples. Shit, she was really getting the guys all throwing money at her, as she quickly left the stage — not before picking up all of the money first.
She looked up and saw me and I realized ... THAT was my mother. I left, getting on the bus and getting home.
I got to my room and jacked off, coming in buckets quickly. I cleaned up the bed, and took a shower, finding something to eat while plopping in front of the TV.
The front door slammed and Mom had come in crying, and went to her room and slammed her bedroom door. I felt just as bad, and I went to her room and knocked on her door.
"Mom, let me in please?"
She opened the door a little and said, "I'm sorry Will, you shouldn't have seen any of that — but its real good money."
"Let me in, please?" I asked again.
She had a robe on, and may have been naked under it. We both sat down on her bed.
"Mom, I had no idea that you were so beautiful — of all the girls in that place, you are truly gorgeous compared to the rest of them."
I could see that she was quite nervous.
"Mom," I said, putting my hand on her face. "I understand why you're doing this, for the money and for us. You deserve to be stripping in a nicer place though, and you need more current music."
"You just saw your mother strip herself topless, and the first thing you mention is the music?"
"Mom, I don't mind you stripping, don't be ashamed of it — embrace it, you could be a headliner somewhere. Is there still a circuit like in the old days ... with those breasts — you could make thousands of dollars, give up teaching completely."
"Will, hold it for a minute, so you are OK with my stripping, and want to manage me to strip for a living full time, is that it?"
"Sure, I'm twenty, about to be twenty-one! You need a few nicer outfits, and better music ... but I was completely hard before you took a single thing off, and I hadn't yet realized it was my mother at that point."
"What exactly would you expect from becoming my manager honey?" she said leaning back, her robe opening a bit.
"Ten percent, off the top — I've almost got a marketing degree, I could put it to use letting the world love 'Sunny Delite.' I think you might have a trademark problem with that name Mom? We could brainstorm and make you a star!"
"Oh, Will — I was so worried when I saw you there, actually embarrassed that my own son saw me like that ... especially when you ran out. By the time I was outside you were already gone. You really think I'm any good; I was hired because the owner wanted to see my tits, but he kept letting me come in and work, sometimes as a waitress, but getting on stage was the real money. So I got you hard, Will?"
"Yeah, the minute I got home I wacked off, just thinking about those beautiful breasts of yours Mom, how big are they any way?"
"They are F-Cups honey, the underwear I need is so expensive, I wish I'd had reduction surgery when your dad was still around, but since you — and everybody else — likes them so much, Are you hard right now, honey?"
"Oh, god yes — Can I see them up close, please?"
"I-I don't know Will, that's..."
"Mom, I love you, you're beautiful ... That's it! 'Beautiful' that will be your theme music. Just a second?"
I went and got my IPod and started the song, and Mom got up, moving to the music — it was fantastic as she was rubbing herself all over her body to this. She was shaking her butt, and really dancing well, and at the point the music was Christina trilling Mom tore off her robe, showing me her entire body, F-Cups and all. I stood up as she teased me getting close to me.
As the song ended I grabbed her and gave her a kiss, all the while her body was up against mine, causing me to tingle a bit. She wasn't pulling away, so I pulled off my shirt, dropped my pants as we leaned down together on her bed.
I put my head between her breasts and couldn't stop enjoying myself. I pulled my boxers off, and she said, "Will, instead of 10%, how about we fuck anytime you want?"
I was using my hand to get the rest of the way hard, then, in a single stroke filled up my mother with my hardness.
"Ooooohhh, William — that really feels good, honey — come on now, Cum for Sunny!"
My only other experience in this situation was by watching porn and jerking off.
I remembered what I saw and started to fuck my mother, fast in — slow out, over and over as her F-Cups were shaking a whole bunch. I had been kissing my mother but really wanted to suck on those tits of hers, so I moved my mouth to her left tit and really sucked and licked all over. I moved to the other one, just as I felt myself about to cum.
"Mom, I'm about to cum -- where?" I asked getting almost too close to pull out.
"Pull out honey, I haven't been on the pill in over five years?" she said.
Begrudgingly, I pulled out and came all of over her chest and tummy. She started rubbing her hands through the mess; even bringing a finger to her lips and licking my seed, causing me to jerk one more spurt into her belly button.
"Oh, Will — that was so naughty, and so good, have you ever had a blowjob?"
"N-no Mom, let me clean up first?"
"No way, I want to taste the two of us on this wonderful weapon of yours," she said, getting off the bed and grabbing me by the balls, squeezing me real hard.
"Honey, you are going to love this — until you get condoms or I get back on the pill, we need to be more careful, nobody would want to see a pregnant woman strip?"
She put her mouth on me and started to slurp, getting me hard again and cleaning me.
"Mom, you sure?"
She was still playing and licking on my dick and said, "What honey?"
"Are you sure nobody would want to see a pregnant woman strip? I would!"
"Yeah, that's because the thought of getting your mother pregnant has got you all hot and bothered. I don't think so, Will?" she said getting back to my dick and filling her mouth completely with me."
"How about fucking for a living Mom?"
She sputtered and started to gag, catching her breath and saying, "You mean doing porn?"
"Yeah, you're beautiful — who wouldn't want to fuck you?" I said.
"That's sweet and disturbing honey. Maybe, if I only fucked you, Will?"
"We could make our own video Mom, to see how much interest there would be?"
She stopped sucking on me for a moment and said, "Are you serious about this honey?"
"We do it right, and we never have to worry about money again, Mom," I said.
"That would be nice, so instead of stripping, we fuck on camera together?" she said, putting, my entire dick down her throat.
I was getting close again, which I think she could sense, so she took her hand and started to jack me off, with her mouth on the very end of my dick.
"Ooooh, ughhh - Sunny, take it — take it all, all of my cum."
I was surprised by how much I had cum and in her mouth, she opened her mouth as if to show off, then swallowed it — and smiled at me!
"Mom, I suggest you start stripping more often, and we save up for making our video. When we have enough, we rent some equipment, film you taking it in the pussy and the butt, and cream pie both as well, how's that sound?"
"I need to get back on birth control, don't I?" she asked.
"That or a prescription for those Plan B pills," I suggested.
"You don't think that I'm too to old, Will?"
"Mom, you are so fucking beautiful — We should get you some hot new clothes for stripping?"
"OK, honey — whatever you say!" she said with a very strange smile on her face. "Fuck me again, Will ... please?"