My first older woman, PART 2, [mF] | 2016

This is PART 2 of a true story that happened when I was 19. I am now in my 30s.

Disclaimer: This is long. 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:

After finger-banging the dentist's wife in the mall parking lot, we both set our sights on actually fucking each other. We still talked via IM and on the phone every day, but the main subject was usually getting my dick inside of her pussy. If we spoke on the phone, we always ended up masturbating together. She'd call me out of the blue sometimes from her laundry room (they NEVER go in there, she said) to do it, sometimes even when her husband or kids were home. Things were getting more daring.

During one IM conversation, we came up with a simple plan. She would drive over to my parents' house one day (while they were at work) park inside the garage so no one could notice her car there (her sister lived just down the street!) and then she could sit on my cock and ride it all afternoon. I told her I wanted her to wear that plaid skirt again, and I wanted that to be the only thing she wore while she fucked me. We had the whole thing planned out in our IM conversation, and we were going to do it the next day.

I went to sleep that night full of anticipation for the next day's encounter, but woke up to a phone call at about 2 a.m. It was from her number. My first thought in my sleepy state was that she was sneaking around, wanting to masturbate on the phone again. I was happy to see that she was calling, regardless of the reason, and answered the phone.

"Hello?"

A man's voice was on the other end. "Is this guy who's been fucking my wife?"

I was stunned. It was her husband. He found out about us somehow. Not knowing what else to say, and also being a kid scared out of my wits, I just hung up the phone. He kept calling back, leaving ranting voice mail messages. I made sure the doors were locked. My parents were sleeping. What should I do? I kept thinking: "Jesus Christ, I fucked up now. Some old dentist is going to kill me Little Shop of Horrors style."

He eventually stopped calling, but I couldn't sleep and signed onto the computer. ICQ fired up and there were messages from the dentist to me, on his wife's account. Basically, what happened was this: He needed to use the computer for something, sat down and saw the IM messages between her and me about planning to meet the next day to fuck at my house. She had been careless and left them open. The dentist flipped his lid, obviously, and when she realized what was happening, ran to the breaker box and cut off the power so he couldn't read anymore of our messages. She just panicked. But the damage had been done.

The next day, while my parents were at work, he started calling our house phone and leaving messages, referring to himself as "Dr. So and So" and asking for them to call him back "concerning your son having an affair with my wife." I erased all of the messages, but came clean with them (somewhat) that evening so they wouldn't be surprised about anything. My parents laughed about it and said not to worry about anything (I told them I didn't know she was married and that all we did was kiss -- even though we never did kiss and all I did was finger her pussy till she came all over me). I lived in fear for the next several weeks, afraid he'd show up at my work with a gun or something, but things were quiet after the first couple of days. Things blew over. I decided I wouldn't contact her and just let it be.

I moved to New York and started classes at NYU that January. One day, my dorm room phone rang. It was the dentist's wife. I asked her how she got my dorm room number, and she said she got it from my mother by posing as someone from financial aid who needed to speak with me right away. Clever.

She apologized for what happened and seemed to think the whole thing was all her fault. It wasn't of course. I was an adult. I knew it was wrong. I worried that they had divorced and that I had helped wreck a family, but they were still together. I was so relieved. We hung up and I thought that would be it, but she called again the next day. And then the next. She always did the calling. Pretty soon, we were masturbating over the phone together again. Every time I spoke to her I implored her to be careful. She said she would be and could handle her situation, that her marriage was her business, etc. I continued on, but felt enormous guilt all the same. Still, it didn't stop me. I still wanted to fuck her totally-shaved little pussy. So bad.

One day we were talking on the phone and I complained that I needed to find a part-time job so I could afford some things I wanted, like a bike to get around the city with, an mp3 player (they were brand new at the time) and things like that.

"If you work and go to school, you won't have time for me," she said.

I told her we could always find time and not to worry. A few days later, I got a card in the mail from her with $500 cash in it. It was for the bike and the mp3 player. I wish I could say I sent the money back, but I didn't. And she kept sending more and more money as weeks went on. Her husband's money, mind you.

I planned to come home for spring break, and she wanted to see me so badly that she sent money for the plane ticket. Her husband was really into baseball and was going to take their kids to see a game about four hours away on one of the days I would be in town. That would be the day we could meet up and finally fuck the shit out of each other.

We discussed how we would do it and where it should happen. Her house seemed logical, since they would be out of town, but we nixed that idea just in case something went wrong. Her idea was to just meet at a hotel, so that's what we decided to do. She wanted me to pay for everything, then call her and tell her the room number so she could meet me there. And she insisted on paying me back for the room because I was just a "broke college kid."

I remember waiting in the room for her, still kind of afraid of getting caught. Part of me was afraid her husband would suddenly appear at the door! Selfishness prevailed over fear, though. She showed up looking almost exactly the way she did in the department store that day. Plaid skirt, sexy legs, long blonde hair flowing behind her. She was thrilled to see me but suddenly shy. We weren't in a dark car this time. I was nervous too, and afraid to make a move.

At one point she turned on the TV -- to the baseball game her husband and kids were attending. Awkward. Seemed like she was having second thoughts.

We talked about how nervous we both were. I said that was funny considering how many times we had masturbated together over the phone. The idea came to me that that's how we should start -- just masturbate in front of each other. She said she was too nervous to do that, so I told her to get under the covers and do it while she watched me.

That's what she did. I sat in a chair near the bed and pulled my cock out. Rock fucking hard. About 7.5 inches long and nice and thick. She just stared at it with the horniest look on her face. I could tell she was slipping off her panties and touching her pussy. No woman has ever looked at my dick like that since then -- she just stared at it, licking her lips a little while touching herself.

I was about to die, I wanted her pussy so bad, so I stood up, ripped the covers off and got on top of her. She kept saying my name is that sweet Southern whisper. She was completely wet. I slid the entire length of my cock inside of her pussy. Balls deep. Soon, we were fucking really hard and fast and she was cumming with me inside of her.

I remember she got on top of me after that, took off her blouse and bra and put her C-cup titties in my face. Huge nipples, OMG. To this day, I dream about those nipples. Slightly puffy. So yummy. I realized the baseball game was still on in the background as I slid my hands under her thighs and pounded her like a jackhammer while she was on top. I wouldn't let her do any of the work. I came in her pussy three times that day, and on her face and tits once. She said she had never let anyone cum on her face before.

After we fucked, we cuddled and talked until it was time for her to go home. When she left, she put a $100 bill on the dresser to cover the hotel room. I thought, "This must be what prostitutes feels like." Haha.

We continued to talk on the phone after I went back to NYC, but one day her husband found out she was talking to me again. Not sure how he caught her, or the details, but I didn't hear from her again for years and years until I got an email from a total stranger congratulating me on a career promotion that had been published on the Internet. I wrote back but didn't get an answer. But it must have been her.

A lot of time has passed since my affair with the dentist's wife. A few years ago, while visiting my parents who still live in that small suburb, I took a quick trip to the grocery store around the corner for something we needed for a barbecue. I got in line behind an older woman who had an amazing ass and a cart full of groceries. The woman turned around and offered to let me go in front of her, but I refused -- wasn't in a hurry. It took me a minute to realize it, but it was her. She didn't recognize me. Like I said, a lot of time had passed. I listened to her talk to the cashier as if they were old friends. That voice hadn't changed a bit. Sexy as ever.

After paying for my stuff, I hurried out to the parking lot and watched her unload groceries into the back of a luxury SUV. I thought about saying something to her, but decided not to in the end. After all, I'm a married man now. :-)

And that's that.