My first older woman, PART 1, [mF] | 2016

This is a true story that happened when I was 19. I am now in my 30s.

Disclaimer: This is long and will have two parts. Also, I'm not the greatest writer. It's not the sexiest story out there, but it's 100 percent true, and I thought some might find it interesting.

Edited for: Typos.

Here we go:

I had just dropped out of college with a plan of moving to New York City and attending NYU. First, I needed to save up some cash, so I decided to move back in with my folks for a few months.

My parents had moved to a new state while I was in school, so moving home was not like "home" at all. I stayed in the guest bedroom of their new house and quickly found a job delivering pizza (fast, easy cash). My parents worked during the day and I worked at night, so there was privacy. Still, with no friends around, I got pretty bored during my spare time and started spending a lot of time on the Internet.

ICQ became a favorite time-waster. It is (was? not sure if it's around anymore) instant messaging software that let's you search for friends/strangers who are also using the site by their location. One night, I searched for people in my new town and only one username popped up. The person was online, so I sent a message saying hello. I can't remember what we talked about that night, but I do remember that she was super suspicious of an online stranger suddenly hitting her up.

It got to the point where me and my new ICQ friend would chat for a little while almost every day. We'd talk about politics and our daily lives. She liked my stories about the funny things that happened while delivering pizza. I learned that she was in her late 40s and was a wife and mother of teenagers. Her husband was a dentist in town. They didn't live too far from me -- maybe 5 minutes away. She said she wasn't in love with her husband anymore, but wanted to stay married until her kids were in college. I thought that was so sad. She was, basically, a bored housewife with a lot of money. Shopping was her hobby. She was also religious. Baptist. Went to church a lot.

After a couple of weeks, we decided to upgrade our daily chats from ICQ to the phone. The first time I heard her voice, I was floored. Super feminine, sexy and Southern. She really was a Southern Belle in a lot of ways. The sound of her voice alone made me hard. Up until that point, we had flirted slightly but never talked about anything sexual. I was lying in bed as we spoke and started rubbing myself through my pants. I guess she could hear it in my tone, because she asked what was wrong with me. I decided to just blurt it out:

"Your voice is making my cock hard," I said.

Her tone suddenly got super whispery. "Oh my God, reeeeaaally?" she said.

"I'm going to have to stroke it now," I said, as I unbuttoned my pants to pull out my dick.

"Sounds like you need to get fucked," she said -- and OMG when I heard her say that, I almost lost it. Just something about a woman of her age and with her social status (and who was Baptist!) using words like that.

The rest of the conversation is sort of a blur, but she listened to me jerk off, talked dirty to me a little in that sexy Southern accent (kept asking me if I wanted her to suck on it and told me that her pussy was getting wet).

When we talked the next day, she said "My hubby thanks you, and I thank you." She didn't mean that literally, thankfully. She said she got so horny listening to me stroke it that she had to fuck the hell out of her husband that night, and they hadn't done it in ages. I said I was happy to help, but would much rather it be my dick inside of her pussy, especially if I'm the one making her wet. She said for that to happen we'd have to meet in person. So we decided to arrange a meeting.

Now, keep in mind we hadn't seen each other yet. At this point in Internet history, not many people had photos of themselves online. Hardly anyone had personal scanners at home and there were no cellphone cameras yet. We described ourselves to each other. I was just an average 19-year-old of average height and weight. Wore T-shirts and jeans a lot. She said she was petite with longish blonde hair, which sounded amazing to me, but she also often said that there's no way a young man like me would want to be with an old woman like her, so I worried that she might be super wrinkly or something. Haha.

We decided to meet for the first time in a public place, but she also didn't want to make it obvious that we were together. It was a small town -- a suburb to a larger city, really -- and she grew up there and knew everyone. Her husband was the top dentist in town. Her brother was principal of a school there. Everyone knew her, so it was risky. We chose to meet in the lawn/garden section of a local department store -- just kind of "bump" into each other, say hello for a few minutes "like you are a friend of one of my sons or something" (her words!) and then decide for ourselves later if we wanted to take things further.

She told me she would be wearing a short plaid skirt. That's how I'd know it was her. I told her in a previous conversation that I had a thing for women in plaid skirts, so she must have made a mental note. I showed up in the lawn/garden section. It was November, but there were lots of fake Christmas trees set up for sale. I hung around a big white tree decorated with blue lights, and peeked down the aisle from time to time. Then I saw her coming my way. My first thought was, "OH MY GOD, SHE'S SEXY AS FUCK and cute as can be at the same time." The way she was walking in that skirt with her long blonde hair (it reached more than halfway down her back) swinging back and forth, I wanted to bang her right there in the fake snow by the potted plants.

She spotted me and approached me. Seemed super nervous, but was smiling. We made small talk for about a minute and then she said she had to go, and just walked off. I watched her hurry to her Lexus and then speed away. I was dejected. Was pretty sure she wasn't in to me. She'd probably realized that I was just a kid and came to her senses.

We talked the next day, like always, and she swore she was just really nervous about someone she knew seeing her talk to me and having to answer questions. She had a tendency to let things slip without realizing it. She had already told a church friend about one of my funny pizza delivery stories, and the friend's only reaction was: "You have a friend who delivers pizza????"

I asked when I could see her again, and she said she was was going to do some shopping at the big, fancy mall in the large city we lived near, and that we could meet there and walk around together and not have to worry about someone seeing us together (although that was slightly still possible). So that's what we did. I followed her around the big clothing stores, staring at her ass as she shopped. I tried to hold her hand, but she wouldn't let me do it for long.

When the shopping was over, I walked her to her car. It had gotten dark. She told me to hop in so she could give me a ride to where my car was in a connecting lot. We sat in her car for a while, talking and laughing and stuff. She was wearing black pants made of a stretchy-type material (again, her ass looked amazing in them).

I decided to make a move and put my hand on her knee. I remember seeing her glance down at my hand nervously and take a deep breath, then I slid my hand up the inside of her thigh and onto her pussy. She said, in that cute Southern accent, "You don't waste time do you?" as I played with her pussy through the material. Her windows were tinted, thank God. She sank back in the leather driver's seat and opened her legs wider. I slipped my hand inside her pants (she wasn't wearing panties) and touched her bare pussy. It was soaking wet. Dripping wet. I fingered her, rubbed her clit and played with her pussy (got three fingers inside) until she came, squeezing her legs together, trapping my hand between them. OMG it was fucking hot.

TO BE CONTINUED IN PART 2 (if you're interested)