I had a colleague who worked for another organization in the same neighborhood as my office. Over many years we met occasionally in official capacity. She was of South Asian descent, very thin and always wore very tight jeans, usually brightly colored. We got along well in those interactions, though I could tell she was a bit of a Chatty Kathy, IYKWIM.

One day I ran into her at the bustop. As we chatted, another man of south indian descent joined us. I saw him turn and give her a serious eye fucking from the back. I had to laugh because it was so obvious, but didn’t tell her why until much later. We shared seats and talked on the short ride home. We got along very well and were laughing quickly. To our surprise, we got off at the same stop. We walked to our places and were further surprised to see that we lived across the street from each other - almost literally. Our chit chat was fun and easy and we compared local restaurants. So we decided to grab dinner at one.

The dinner was a great time. She was the most talkative dinner date I ever had. She kept going on and on. But she was smart and interesting with a full life story (immigrant, fun family, a recent divorce after 1 year of marriage, super into music, etc.). And not having to chat much relaxed me and made me more confident. I could just sit back and enjoy the show. At one point I got the spark and wondered if this was turning into a “date”. Other than her nice ass, I hadn’t been attracted to her before. She had a cute face, but it just wasn’t there. But she had a new haircut that suited her very well (shoulder length that curled inward like a 1960s dancer) and our chemistry was unmistakeable.

We walked back and she invited me up “to see her building”. I knew then that this was on. On the way up I checked her out moreso and got hard in the elevator as she stood next to me practically poured into those jeans. I don’t remember what I was wearing, but it probably showed. I do recall it was early fall and we didn’t have jackets or extra layers.

We went into the apartment, which was on a high floor and had a gorgeous view of downtown. She had two cats and lots of plants. She turned on some blues music and poured some sparkling wine. We sat on a couch overlooking the window and talk a long time - mostly about our city, what we loved and hated. She leaned back on an arm and draped her legs across mine.

After maybe a couple of drinks the conversation was slowing down. She leaned forward and faced me. It was awkward because of how we were sitting. She just sat there staring at me. I knew what she wanted because there was no other reason to be doing that. I pulled my legs down, moved over and kissed her gently.

She was pretty aggressive and it quickly evolved into a full makeout session. This was like high school as we made out for maybe 20-30 minutes and I rubbed her jeans and felt her up. She finally took off her sweater and I was surprised to see she wasn’t wearing a bra. It was so hot watching them bounce out of the sweater! Her tiny tits stood straight up at attention. I pushed her down and started aggressively fondling her and kissing her up and down her neck and sucking those tits.

She said “let’s go” and pushed me off and walked me to her bed. Walking behind her with a naked top and that wonderfully cute ass in those tight jeans was sending me to the moon. We rolled onto the bed and started taking off the rest of our clothes. I confirmed she was on BC and resolved to take her raw.

We fucked the evening away as the sun set. Her windows were wide open but we were on a high floor so people didn’t likely see much. We did all the basic positions except doggiestyle. At one point I flipped her over but she immediately rolled fully around onto her back. Maybe she didn’t like doggie or just wanted it missionary. Didn’t matter because we were having a great time. There weren’t too many other awkward moments. She was pretty wet so I could push deep into her and thrust as hard as I wanted. My favorite memory is when she spread her legs completely wide and let me go in super deep. She held them up as I pushed in as hard as possible. I then wrapped my arms around them and put them around my shoulder. That’s what made me finally cum in her pussy.

Afterward, we rested a bit and did that nervous “look at what we did” giggle as we laid naked above the sheets. As normal for her, she immediately started talking. Without skipping a beat, she grabbed my dick and started stroking me while she continued whatever train of thought she was on. However, I still hadn’t recovered and couldn’t get hard. I pulled her hand away and spent some time kissing her nipples and massaging her tits. I was kind of mentally exhausted, so decided to call it a night (it was a weekday) and went home.

This was before smart phones and texting. So we chatted on the phone the next day but her rapid fire chatter turned me off at that point. We did meet again that weekend. The date didn’t go that well, but we did end up fucking once more and it was pretty hot. I’ll probably write about that next.