J was one of the few I did not screen at all - very light/mild to none at all. She simply knew that I found her attractive and I was pretty sure she found me attractive as well.
The next day she txted me and asked if she could call me to talk on the phone. I told her I was eating and I will call her after I am done. J sounded pleasant on the phone. Kind of ditsy, but I liked her voice. I teased her as to whether she did this with all guys and she said she didn't, but she wanted to make sure I was who I was and there was some flow in the conversation. I suppose I passed because she agreed to meet up the next night at a low key bar in her part of town.
Did my standard calling to let her know I was on my way right before meeting up for our first 'date'. I arrived a bit early and waited in my car until she txted me that she was waiting inside. I got out of my car, walked to the bar, entered, then gave her a hug and told her she looked nice - great cleavage on display with nice skin tone and smile.
Conversation was very easy and smooth flowing with J on our first meet. It almost took us too long to glance at the menu to decide what we were going to order because we were already engaging each other with good conversation as the server made the rounds asking us if we knew what we wanted. J got some type of cocktail and I got my standard beer. In all honesty, i'm better at communicating with women sober. It used to feel as it were the opposite just a few years ago. Anyways, our drinks came out fast as we continued to talk about hobbies, work and life, including treading maturely on a sexual topic or two. Once I was done with my drink, she ordered another cocktail - this girl can throw them down. Turns out she had a background in serving at a club in her 20s. Oh, yeah, and our tastes in music were almost the same, which is always nice.
After she was done with her drinks she got her credit card out and payed for them willingly as I threw her some for the tip and my beer. Easy peasy. No expectations that I should pay or anything. Cool. We walked out together towards her car. I kind of felt she'd invite me back to her place, especially since she was a bit boozed up with a couple cocktails in her. As we were walking I got the vibe that she wanted me to grab her hand. I hesitated and didn't, but all was well because I ended up giving her a hug and then went in for a peck on the lips as I was starting to pull away from the hug. She was very responsive and then we started to make out as I spun her around to check her out a bit more. Such a sexy chick, looking more in her late 20s than mid 30s. I wished J well and to let me know when she's free again so we can plan something out. She txted me 10-minutes later telling me she got home safe along with sending me a selfie she had just taken.
In the coming days we would txt around midday about random stuff that was happening in our week. I then told her I was thinking of seeing a DJ I liked midweek and that she was welcome to join. She had plans that night already, but instead told me she was going to go see another group at a well known place on Friday and if I would like to be her +1 - she had a lot of hookups in the city and could get concert tickets for free apparently. I agreed and was actually looking forward to seeing her again. Each day leading up to Friday she would reach out to me with random stuff, mainly music related, still not screening her or her DTF-ness.
Friday had arrived and I was ready for a great night ahead. We touched base around 3PM that day as she told me the time the band was going on at. I responded with a, "Great. Pick you up at 930PM". "Perfect" she said before sending the address.
J was looking sexy again that night. I gave her a hug inside the car as she kissed the side of my neck. We talked about how our days and nights before went. The venue was only a couple miles away, which was nice as we were there entering the parking car garage in no time. This is the venue she worked at some years ago and apparently she knew almost everyone, from the managers, to bouncers and bartenders. Yikes. I knew she was going to introduce me to them, which to me made it seem like I was already dubbed as her bf of some sorts. All good.
As I parked and she began to get out of the car I told her that she had forgotten something and pulled her arm back inside and proceeded to kiss her to more or less continue where we had left off. We walked outside the garage and to the venue together. Surprise surprise she knew the 3 guys standing in front. She introduced me. They were nice to me, but I know they probably hated my guts because they likely never got that there access. She went up to the box office and got our tickets and wrist bands which were comped by some entity. Inside we went, and to greet more people she knew, including the bartender that would get us free drinks. Vodka and soda it was. Two please.
We then made our way to a section that had chairs and tables, where I suppose the wristbands came in handy. We were a tad early, so we sat down next to each other and started talking and enjoying our company, while sipping on our drinks. Smiling, laughing, touching and sneaky kisses away from the people she knew were had throughout the hour long gig. It basically felt like I was her boyfriend as she put her legs on my knees, allowing me to touch and feel all I want. Among the smoothest legs I felt - her exfoliation regimen, as she put it, kept them that way.
It was 11:30PM and the show ended. We said goodbye to her friends, including the guys at the front door, and walked hand and hand back to my car. She said how it was still quite early and how there is a cool, small club a couple blocks from her place that we could go dancing. I said fine, but honestly didn't really want to go and just wanted to go back to her place to 'chill'.
Once back on her street and in front of her car, she said I could park and come in and how she needs to change shoes. In I went. Her place was low key and comfy. She made me a vodka soda and her male roommate, who is in his late 40s, came out. Now, she'd told me about her having a male roommate before, but though this guy was nice and all, he did not come off as the type that could get her - writer/bookworm/articulate type. J made us a drink as her roommate went back into his room. We settled down on the couch as she went in her room to pull out a couple pairs of shoes that she tried on for me to decide which to take out dancing. I chose which ones looked best on her with her dress and she put them on and sat next to me on the couch. We chatted a bit more about the night with our drinks in our hands. She asked if my drink was too strong, and I told her it was just right, but that I thought she tasted better, as I went in to kiss her, this time with more groping. In the back of my mind was the roommate coming out, but it was all in the back of my mind as we proceeded to make out some more. She then said, 'looks like we're not going to go dancing then?' and got on top of me and said 'oh is this what you want?', allowing me to grope her ass and motorboat her tits through the dress.
J then said something along the lines of how we weren't going to have sex, but that we could cuddle. For half a second my rational mind thought "fuck", but then I remembered how it wasn't the first time i'd heard that in that kind of situation and it definitely would not be the last. I led her to her room, where she then turned on some music from her iPad and lit some candles. I pushed her down on the bed and started kissing her heavily with my knee putting pressure towards her pussy. She was not deflecting any of my actions and was quite welcoming in fact to me touching her on her inner thighs and squeezing her ass underneath her dress, until I was able to slide my fingers down and into her pussy. She had a very small vagina that two fingers was pushing it. I put her hand on my pants so she'd feel my rock hard cock through my jeans. She didn't hesitate to unbutton my shirt and pants from there on as I proceeded to continue to finger bang and rub her in every which way as I licked her tits and we nibbled on each others lips. She moaned louder and louder, growing wetter and wetter, that I told her, 'shhh' because of the roommate. "I don't give a fuck", she said in a moaning tone as she stroked my cock.
J's oral skills were quite average as in she wouldn't let me bust in her mouth, but willingly licked my balls and up to the shaft like the good girl she was/is. She told me she wanted me to fuck her, so I did, gladly. Fucking her at first was like fucking a girl in the ass - I could not thrust and she had to go at her own speed/pace. I'm not huge, by the way, in case you were wondering. Anyways, I came rather fast, but knew it was inevitable with all of the four play that we'd been doing. All good. Round 2 (for me) would be coming up fast. As long as I was continuing to work her pussy with my hands and fingers, J was a happy girl.
I don't eat pussy willingly. It has to be clean shaven/smooth and not smell too horrid, for me to want to go near it. Suffice to say, my mouth and tongue was all over her. Tasty. "Put a finger up there", she said. You got it. I then fucked her again, this time her pussy adjusted allowing me to go harder until I finally came. We then got under her covers naked and cuddled with my cock pressed up against the top of her ass. Felt nice. Oh yes it did.
Then she asked about how many women i'd been with that were older than me and how she bet my mom's friends all wanted to fuck me. As well as jokingly saying that she wasn't a bootycall and that next time we'll go on an actual date. Basically jumping two steps ahead. This I suppose was the down fall as I told her I had to go. She wanted me to spend the night and make breakfast when we woke up. It was already nearly 4AM, but I simply told her that I don't do sleep overs on the first time. She understood and told me she wanted me to fuck her again and how horny she is (masturbated every day).
J layed down on her back and I proceeded to fuck her tits until I came, giving her a nice pearl necklace that made its way to parts of her hair. "This is great", I thought, before giving her one last kiss and getting my pants on and out of there.
We've not contacted each other since. Personally I like the woman to engage first after sex no matter if it's a simple 'hello'.
Anyways, it's my birthday tomorrow and she knows it too. I suppose if I don't get a 'happy birthday' from her then it is over.
I'd like to see her again though. If not, I wish her well.
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