My name is James, and back in college, I met a woman named Caitlin. At the time, she was twenty-one, and had a solid c-cup rack. I was twenty-one as well, and I found her to be very attractive. The one sour note was, that I never asked her out. I never got to sleep with her, and I always regretted not doing it. I guess we weren't friends, and more like acquaintances. Anyway, I never heard from her after college. She could have moved far away for all I knew. Unfortunately, I couldn't find her on Facebook, or anything else.
I guess she may have gotten married, and changed her last name. Hell, she could have gotten plastic surgery for all I knew. Although, I knew this, I might be able to try again sixteen years ago. That's right, I have my own time machine. I knew where she was back then, so I went back to when was twenty-one. By then, I was thirty-seven, so I'd still look sixteen years older. I setup the machine, so I could go back to the year 1998, and see the woman I had been obsessed with for all those years. Going back was quite an experience, just how you see it in the Back to the Future
I felt different when I got there, and I was more than ready to find Caitlin. I remembered her schedule for that year by heart. Back then, they didn't have so much security at the schools. I just said I was a substitute teacher, and I was in. I just had to make sure I never let myself see me. That would just be a big problem, and I probably wouldn't be able to accomplish my mission. I did see my other self for a minute, and I couldn't believe I used to dress like that. Skin tight jeans, and everything else. Anyway, I stayed out of sight of myself. I stayed close to Caitlin though, and watched her.
After school, I watched her go shopping. She went looking for some clothes, which included some bras, and panties too. I never knew she went shopping alone for that kind of thing, but I liked it. After a few hours of watching her, I almost forgot what I was doing. I should have been thinking about how to approach her. I had no idea how to do that exactly. I had sex with many women in those years, but this was one special lady, so my confidence was shot a bit. Although, at one point, she started things. She came up to me, and said hi.
"Aren't you a new substitute for the community college not too far from here?" she wondered.
"Yes, that's right," I replied, as I didn't look her in the eye.
We made a little chit chat for a minute, but she had to go. I couldn't let that be it, so I asked her to get some coffee. She accepted, and we set a time and place. The next day, I met her at a small coffee place that was by the mall. I just had to wonder if all that stuff, was still there in there in my time.
"So, you aren't seeing anyone right now?" I wondered.
"No, I like being single in college and have endless possibilities," she replied.
I liked the sound of that. So, it seemed we had some chemistry with each other, so I continued my little charade. It became difficult to not give myself away, because I had to keep up with current references, and avoid other people that may recognize me. After a while, I had gotten closer to her. We maintained a simple friendship, and kept it out of the eyes of the college. I definitely noticed that she was much prettier than I remembered. She got my motor going, and I was afraid I'd make my move to soon. Eventually, I asked her out on a date. After class, I made sure to meet her outside.
"Hey, Caitlin," I said.
"Hello, what's going on with you?" she pondered.
"Well, I just happen to have these two concert tickets to see Green Day, and I thought you might wanna come along," I told her.
I knew she was a fan, and I bought the tickets, but never managed to ask her to go. She was a little reluctant, but she accepted the invitation. I picked her up, with a car I had to rent, and took her out. We had a great time, and she certainly began liking me. As the concert came to a close, she gave me a big hug. I was happy, and it seemed that things were progressing. We went out to the parking lot, and got into the car. She leaned towards me, and gave me a simple kiss. Then she made a suggestion.
"Let's go back to my place, for some drinks," she suggested.
It seemed too good to be true, but I was going along with it. I knew where she lived then, because I found myself just wanting to knock on her door all those years ago. She still told me where she lived, and we went in. She got out a couple beers, and came over to me. We opened them up, and we sat down.
"So, what made you wanna take a substitute teacher job?" she wondered.
I guess I really hadn't thought of my back story, so I had to think something on the spot.
"Nothing really, it just happened," I replied.
We began drinking, and she took the cat out of the bag.
"So, just how badly do you wanna have sex with me?" she wondered.
I had a stunned look, and was speechless.
"You are not even gonna deny it? I like that, I mean why else would a sub wanna spend so much time with a student? Even offer to take them to a concert?" she pondered.
We finished our beers, and she came towards me. She sat down right next to me, and laid another kiss on my lips. My plan was to put the pieces in place, but she seemed to be controlling the board. She laid down on her back, and took me with her. We made out for a few minutes, and she eventually, undid her skirt. I pulled it off her, and she took off her shirt. I never got to see her in her bra and panties, and she was easily a million times hotter than I imagined.
I got onto my knees, on the floor, and I was unsure of what to do exactly. She was my dream lady, and it seemed too good to be true. I was so glad I had the technology then, but that still came with some big responsibility. She pulled me onto her, and undid my pants. She felt my hard cock, which was throbbing. I slowly pulled off her panties, but I didn't look at her pussy though. She pushed my pants down, with my boxers. I stuck my cock right into her, and it was beyond amazing.
"Oh, I love older cocks," she muttered.
I began thrusting my cock, and I was so happy I finally got to fuck her. We kept eye contact, and she kissed me a few times too. A minute later, she took off her bra too. I had no idea what her exact intentions were, but I didn't care. I put my arms underneath her, and held her a little closer to me. I kept my thrusts consistent, and made love to her.
"Come on, James, fuck me a little harder, this maybe the only time this happens," she said.
Well, I obviously couldn't stay there forever, so it would be fine, if it was a one time thing. She kissed me several more times, and put her hands on my head. It seemed more than a fuck session, it was something more. I wanted to pleasure her all I could, and make her remember me.
"Fuck, James, shove that cock in there deep. I want to feel every single inch of it," she moaned.
I gave her what she wanted, and began thrusting my cock harder. My heart was beating, and I felt like I was going to pass out. My emotions were all over the place, and she just wanted more. I couldn't help but give her what she wanted and then a little more after that. I leaned down and took a look at her boobs too. They were real, and spectacular too. I couldn't hit myself enough for not asking her out back then.
I leaned down, and began licking her nipples. She had small nipples, but they were still very sexy. I began sucking on her nipples too, just how I masturbated thinking about doing that many times before. I made her moan, and hearing that made me want to cum right inside her. I did my best to hold off, but it couldn't have been more difficult for me. I was breathing really heavily, and she could tell what was coming.
"Shoot it inside me, I want it in there, right now," she demanded.
I couldn't do that, what if I got her pregnant in the past, that would really screw things up in the future. I made sure to pull out, and shoot it right onto her stomach. It was so great, and I only had to wait sixteen years to feel that feeling. She felt some of the cum, that was on her stomach. Then she leaned over to my cock, and took it right into her mouth.
I still had cum oozing out of my cock, but she still took it right in her mouth. She sucked on it, and made me throw out some more moans. In those years, I could have had countless blow jobs, so then I wanted beat my head against a wall, for not asking her out. She looked up at me, and I looked back at her. She loved pleasuring me it seemed, and she was out for more of my cum. I put my hands onto her head, and made her go down a little further on my cock.
"Oh, Caitlin, you are one dirty student," I moaned.
She knew that, and knew it well. I never got that vibe from her back then, but after that, I already felt like cumming again. I did my best not to, but it was no use. I began moaning again, and she backed away a little bit. I came all over her face, and I felt spent.
I really couldn't comprehend everything properly. Although, when someone knocked on her door, I made sure to hide. She wipe her face, got dressed, and went to the door. She opened it, and to my surprise, it was past me. The past me was standing there, and I had no idea why. I never remembered doing that, but I must have changed things.
I heard myself ask her about the friendship with future me, and she said we were just casual friends. That would be bad if she was dating a sub, so then past me actually asked her out. I obviously couldn't date her in the past, so I grabbed my clothes, got out of there quickly. I guess future me, gave him a conversation starter. I went back to my own time, and things were different. I was married to Caitlin, and we had two kids too. So, I unintentionally changed the future, but it was definitely better. I would definitely not go back, and try to change it back.
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