During my college graduate program, I met a female classmate who became a FWB. I was a small town guy and only knew about sex play with women in a more "traditional" manner. I did not realize at the time that she was way more adventurous and way more experienced than I was.
I grew up in a small rural town. So when I saw a dildo on her nightstand by her bed, I asked about it. I tried to just seem curious and I asked what things would you be doing with that even though I knew - or I thought I knew. Of course I thought she used it on herself when she jilled-off. Her response was "James uses it on me when he stops by." I thought that would be fun to use it on her. I didn't think anything about her with James since I knew she was busy with others besides me. Then she looked at me and said, "and then I use it on him."
That got my attention and I think she was gauging my reaction. I know I had a little surprised look - I'm sure my eyebrows gave it way - but all I said was "that's interesting." And then we started with our standard, routine play and we both needed to do.
The next time we got together the dildo was still on her nightstand along with a tube of KY jelly. We crawled into her bed and started playing with each other with our tongues and fingers. She was pulling on my cock when I felt her finger circle my butt hole. I know I was breathing different once she started probing but I didn't stop her or say anything. And after a short period, I could feel her finger tip wiggling inside me. I think my cock spasmed a little and got harder.
I think she saw me close my eyes and let out a big breath. My cock head was a little wet at the tip when she whispered in my ear, "feels good doesn't it?". I moaned back, "oh yes. Yes it does". She took my cock head into her hot, wet mouth. i could only mosn as i felt her wet tongue slide apund my cum slit. Then she reached over to the nightstand and picked up the KY jelly. She put a little on her finger that had been inside me and then started to coat my little hole with the jelly. It felt cold at first but it made it easier for her to put her finger deeper in my ass.
When she started massaging my hole open, I heard myself releasing a little moan. I reached down to my cock and started to jack. But she quickly took my hand away and said "Just wait. I can see that you like it. I promise you it will be a wonderful experience."
She started with one finger and I could feel when started with two fingers. And then I could feel her working the third finger in to me. With each additional finger my hole became more relaxed and I started to crave her fingers in me deeper. I didn't touch myself but I could feel cum running down from the tip of my cock. I was on my back and she gently moved my knees up by my chest to give her better access to my butt hole.
When she stopped I released a big breath and she said, "it's gonna get better. Just don't open your eyes and relax." So I did as she directed. Then I could feel the head of her dildo pushing at the entrance of my hole.
She continued slowly working it into me while whispering to me, "I thought you would like it. See how it feels when I rub it around the entrance of your opening and put just the head inside of you. That's how I like it when James uses it on my ass when we start. That's how James likes to start too. "
I nodded my head and said "yes I can see why you like it."
