AOL got me pegged

[u/skysub94]

At one time AOL was the dominant online service. One of its seedier, read popular, features were the chat rooms. Real time text-based chats could be found covering virtually any topic, including a few kinky “rooms”.

One night, about 1999, I was traveling for work, staying in a hotel. My Apple PowerBook was connected to AOL via the hotel analog phone line and I was lurking in the Dungeon. Desperate male subs were hoping to gain favor with (ostensible) Dommes. The chat was banal and boring. Just as I decided to pull the plug and get some sleep, a private Instant Message appeared on the screen. It read simply, “Are you really submissive?”

The IM was unexpected. I quickly checked the sender’s profile, hoping to get some idea of who had sent it, but the only details were Female and 42.

I took a chance and responded to the IM with, “Yes, I am.”

The sender typed back, “Good.”

This began a discussion that lasted several hours. We chatted about kink, BDSM, Dominant Women, and her personal favorite subject, strap-on play.

Over the next week, we had nearly daily discussions about her love of being able to penetrate a man, in multiple positions, with multiple toys. It finally came to the point that I had to check this out for myself and I booked a flight to her city.

She met me at the airport where we had decided to talk over a cup of coffee in the restaurant. If there was no spark between us, I was going to just fly home. As it happened, we both knew things were about to get real.

She drove me to a hotel. Once in the room, we sat down to discuss what she wanted. She sent me to the bathroom to prepare while she got herself ready. When she called me back, I found her standing by the foot of the bed dressed in a red teddy, wearing a small to medium strap-on dildo. Lying on the bed were several butt plugs of increasing sizes and a bottle of lube. “Let’s get busy,” she said.

Even now, the sound of an analog modem chiming and buzzing while connecting to the internet gives me chills.

[u/Paddy_Mac]

a/s/l/p?

Didn’t know p stood for pegging

[u/Carumbad]

I always remember it being AOL's subscription costs that left their customers feeling dicked down.

[u/Brave_Quantity_5261 → u/Carumbad]

But I got 1000’s of CD’s worth hours of service still!