Milf in the Suburbs

*These events are a true story. Names and locations were changed*

Much of this country consists of overall decent but devastatingly boring towns. I lived in one of those as a transplant- nothing wrong with it, in fact it was often placed near the top of lists such as "best place to raise a family." I didn't hate it, but I was 25, working my ass off everyday, and didn't have any strong connections here for a release.

In a world so hard to meet new people, I would try my hand at the assortment of dating apps. Sex was one factor, but even just the spontaneity of meeting someone at a new bar, having an interesting conversation, and calling it a night could be worth it. The last couple years, I had a handful of flings with a variety of girls in their 20s. I wasn't the dreamiest guy in the world, but I was a decent height, kept up with working out, had a good job, and had some very specific qualities like my collarbone that women seemed to like. I was able to meet plenty of women, but none stuck around for very long.

The dating apps became monotonous, so much so you sometimes forget who you even swiped right on. One day I checked out one of the apps to see an intriguing match: Sharon, 50 years old. Sure, I've been with some older women in their 30s, but I was almost intimidated by this, always having had a closet fetish for older women. She appeared a little plump with a stomach and large breasts. A round face, oddly cute for a woman her age. She wasn't a drop-dead bombshell, but appeared fun and flirty; a similar aura to a friend's fun wine aunt you met at their family party.

I don't recall the exact details of the conversation, but initially, we never paid any attention to our age difference. We spoke about our jobs, what we liked to do, and quickly exchanged numbers. We agreed to get drinks and appetizers at a restaurant in between our areas. Somewhere along the way, she sent me a risque photo exposing her cleavage. Despite her forwardness, I still wasn't expecting much to happen, still intimidated by our age difference.

That Thursday night, I sat at the bar waiting for Sharon. There were some doubts and anxieties leading up to this moment. What if I see people I know from work? How will I be able to explain getting food and cocktails with a woman twice my age? I began to think of some potential excuses I could provide. Is she my neighbor? Nah, that doesn't make much sense. Would she be offended if I brought it up?

I turned around from the bar and saw Sharon approaching. I smile and ask, "Sharon?" for clarification.

"Hi, Joey," she said, we hugged as we greeted each other. "I can't believe we're doing this," she said with levity. What I thought was going to be a bit more awkward quickly became more comfortable.

"It is what it is," I say, trying to keep cool. "Who cares?" I do, apparently, but I won't act like that.

"You're half my age," Sharon says, as if we don't already know that.

"Yep," I say with a chuckle. "What of it?"'

Sharon ordered a glass of wine, I got a gin and tonic, and we eventually got a couple of light appetizers. We spent some time just getting to know each other and made the occasional jab at our age difference. She was a white collar professional, a single mother: definitely making deep into the six figures. Somehow, the bartender took notice of our situation. "We're on a Bumble date," Sharon said to the bartender. "He's half my age." Clearly, she was actually a bit proud of it. We loosened up with a couple more drinks as we accepted the weirdness of the situation.

"Oh my God," she suddenly cowered a bit in her seat. "I think I know those people over there," referring to the group of women in their late 30s sitting at the table behind our backs. The exact situation I was worried about for myself was happening to her, to equal embarrassment. Good thing I thought about this possibility for myself.

"Hm... how could we say we know each other?" I asked, trying to be playful.

"Maybe you're my financial advisor?" she asked.

"I don't know anything about that stuff." We began brainstorming a few other possible scenarios where two people with this age difference could meet for drinks in a "normal" scenario. Interior designer? Perhaps.

She continued to let her embarrassment be known about the people behind her, trying her best not to make eye contact. I use the restroom, she's afraid to see the people she knows and holds it in. We debated staying until the party behind us left, but decided to make a run for it with me as her shield. I paid the tab, and we made our way to her car.

I was sitting in the passenger seat of her car, and we continued talking as we were enjoying each other's company. She was flirty through the night, so I decided to make a go for it. I work my mouth towards hers, and we kissed. The feeling of kissing such an aged, mature woman on my mouth excited me. We kissed more, and Sharon quickly became aggressive: she stuck her tongue in my mouth and bit my tongue. I grabbed her hair as we passionately made out in her car. "Would you like to come over?" she asked. I accepted, and she said, "but no sex." I never want to assume that in the first place.

I got in my own car and followed Sharon to her house. It looked to be in an upper-middle class neighborhood in a nice part of town. We quickly made our way to her bedroom upstairs. We plopped ourselves on her bed, continuing to make out. I can't believe I'm in bed with such a woman.

I worked my way down her neck and towards her breasts, removed her shirt, and exposed her breasts tightly pressed against her bra. I kissed and licked the top of her breast as I caressed it with my hand over her bra. "Do you want mommy's milk?" she asked. I was absolutely shocked she went there and initiated talking like that, especially so quickly.

"Yes, mommy," I responded, before I could rationalize what was going on. I removed her bra as I suck on her nipple. I could feel and smell her breath as she moaned while I sucked on her tasty nipple, as I laid upon her chubby, warm body. The fact that I was turning on such a mature woman made me immensely horny, and I wanted to continue to please her. I went back up to kiss her mouth, as my hand made its way down her pants. "I want to please you, mommy." I didn't care how far I was going with this weird role play.

I could feel her wet, warm vagina on my hand. I adjusted myself towards the end of the bed, positioning myself at a better angle to take off her pants and work her pussy. Sharon moaned as I went deeper and deeper in. Her pussy was huge, dripping with fluids as I penetrated her with three fingers and caressed her clit with my thumb. Her moans were louder than I've ever heard a woman, taking zero shame in her sexual pleasure. Her moans grew louder and louder, as fluids seeped through to her legs, feeling her breath as she enjoyed this pleasure.

Eventually, I'm splashed with Sharon's cum, exploding through my fingers and soaking up the sheets. "Oh my fucking God!!" she screamed, louder than I ever thought a woman could genuinely scream during sex. I took my fingers out of her pussy and put them into her mouth, then made out with her as I tasted her fluids.

"I want to fuck you," I begged.

"Not now, baby," she replied. Even still, I wanted to please her more.

I went back down to her pussy, this time with my mouth. I stuck my tongue deep inside her pussy, tasting all the fluids from her orgasm. I began licking her clit as I stuck my fingers in her yet again. Within a couple minutes, she already came again, this time all over my face, and screamed louder than before.

"I want you, mommy," I begged, my cock rock hard.

"No, baby." She insisted. "Jerk off for mommy."

Normally, I would be offended, but I was completely at her will. I laid down next to Sharon as I looked at her naked, sweaty body, stroking my cock. She touched herself as she watched me masturbate. "Are you going to cum for mommy?"

"Yes, mommy." I can't believe I was doing this, but I needed to for her. "Am I being good for you?"

"Yes, baby," she replied. Her affirmation meant a lot to me.

My cum shot up in the air. I so badly wanted to fuck her, but I knew I needed to be good for her.

*More adventures eventually continued with Sharon. Look out for the next chapter.*