Our very long journey… still in progress

As much as I’d like to get into the meat of my story, the best way to tell mine is to start from the very beginning – which takes us back about 20 years.
My wife, Samantha, and I are in our late 30s. We met in high school, and being a year older than her, I had dated quite a few girls and even slept with a few of them. Samantha, on the other hand, only had a couple of boyfriends, and they never went to bed together.
We first hooked up when I was 17 and she was 16. She was a virgin, and I was her first. I knew from the moment I met her that she was different, but I didn’t know why. While a lot of the other girls were stick-thin, she was curvy with amazing tits and a round ass. What I didn’t know then was that she was exactly the kind of woman I would grow to love and get horny for. At 16, she was at the point in her life where she was ready to get rowdy and have some fun. The first night we spent together, we went further than she’d ever wanted to with any other guy. We got completely naked and spent the night touching, fingering and jerking each other. We were so hot and turned on that I’d slipped on a condom and started to enter that sweet pussy before I stopped to ask if she’d done it before. I assumed she had because she was all hands with me and really seemed to know what she was doing. I was shocked when she confessed to being a virgin, and I immediately pulled away. As much as I wanted to drill her into the mattress, I didn’t want the start of our relationship to be like that.
We ended up spending a few weeks getting to know each other and each other’s bodies better. About a month into it, we decided to sneak out for the night, each of us telling our parents that we’d be spending the night at a friend’s house. We got a nice hotel room with a big bed and huge bathroom. In the shower, she jerked my cock while I stuck my fingers deep inside her twat. When she leaned in to whisper into my ear, “Make love to me,” I was out of that shower and in the bed with her in no time at all. Our first time was great: I took things slow, and we both had a wonderful time.
After that night, we couldn’t keep our hands off of each other. We screwed like bunnies, anywhere and anytime we could manage. As teenagers, we were even able to do it several times a day sometimes. We took lots of time to learn about what we each liked and disliked, and we did plenty of experimenting. She once told me about how she’d sit in class, looking at the students around her and wondering which ones of them were having sex. She didn’t think it was many of them, and that certainly none of them were getting it as good as she was.
I eventually graduated and went off to college. She was still in high school for another year, but she visited me often, and when it was her time to graduate, she came to my school. We basically lived in each other’s dorms, and of course, we still messed around whenever an opportunity presented itself.
I remember in great detail how one night, I took her fingers and put them over her clit. I moved them in a slow, circular motion, asking her if she ever did that. She shook her head, so I rubbed a little more then let her take over. “How does it feel?” I asked her as I knelt next to her and began fisting my dick. We watched each other closely, and it was the first time we’d witnessed each other masturbating. It was absolutely amazing. When I saw her hips start to stutter, I couldn’t help myself: I crawled up to her face, put my cock at her lips and came when her tongue came out to lick at me.
When we’d cleaned up a bit and were under the covers, I commented to her, “You seemed to know what you were doing down there. Are you sure you’d never done that before?” She laughed and blushed. She told me that she’d been masturbating regularly since she was 12. She told me her favorite way to do it was to get into the tub, spread her legs wide and let the water from the faucet massage her clit until she came. When I went away that first year and she was stuck at home, she said that she’d masturbate in the tub every night. It got to the point that her parents started to yell at her about the high water bills; they couldn’t understand why she was suddenly taking such long baths!
That night turned out to be a huge turning point in our relationship. We were now 21 or 22, and it was the first time we’d ever been so open with one another. It was soon after that night that she started getting daring when we’d have sex. For example, one night she was going down on me. I had my fingers in her hair like usual, and she suddenly reached up, put her hands over mine and pushed down, forcing me deeper into her throat. Another time, I was fucking her doggy style, and I lightly slapped her ass. She moaned loudly, threw back her hips and asked me to do it harder.
Eventually, we started trying out new things in the bedroom. We experimenting with things during foreplay or tried fucking in different positions. We also liked having sex after having a little to drink because any inhibitions we might have left would completely disappear. Unfortunately, it also meant that I came a lot quicker than usual and it would take some time before I could get hard again. I once told her that I felt bad about that, and that’s when she suggested we buy a vibrator. She said she could use it on herself while I sucked her tits or something.
So, the next time I came too early, she suddenly pulls out this vibrator from under the mattress. I watched eagerly as she put it on her clit and rubbed it all around her cunt. I don’t know what made me say it, but I go, “It’s a shame that there isn’t another dick here for you to fool around with.” I bit my lip and looked up at her, sort of hoping that she hadn’t heard me say anything. She didn’t say anything, but she did start pumping the vibrator in and out of her twat. A few minutes later, she says, “Interesting.”
“What’s that?” I asked, my eyes glued to the toy in her pussy.
“Having two guys at one time,” she replied. The moment the words were out of her mouth, her hips started moving faster. I held my breath as I watched her cum harder than I’d seen in a long time.
That was the first time my girl and I had talked about bringing another dick into the relationship, but it certainly wouldn’t be the last time.