Update time

I ended up moving out from my parents house in mid-April of this year, and since then i've just been smashing too much that I didn't feel the need to write about each encounter any more. In short, in the past 13 days i've slept with 5 new women, making it a total of 11 by the midway point of 2015. Not sure when I will tire from it all, but in the meantime i'm enjoying myself and life is meant to be enjoyed. Look good. Live in or just outside a big city. Have your own place. Slay.

M, the 50+ retired nurse/single mom/widow

M had been messaging me for what seemed like months. She'd send me sexy pictures and try and tease me over the weeks and I just went along with it. I flaked on her many a times since she was the furthest of a backup I had.

In short: I was on a 1 week no fap (powerful in lowering ones standards), I picked her up around 10pm on our first meet-up, drove to a dark part of the neighborhood, got in the back, she gave me a bj, she got in the doggy position and I went to town for a little.

"Oh I got my tubes tied 15 years ago, you don't have to worry". I said "Oh okay". As she was on all fours I snuck a non-latex condom on, stuck it in and penetration commenced.

What was funny was how she thought I had not cum since she was unable to see me quickly take the condom off and set it on the car seat floor. She insisted I try again or that she could 'finish me off'' with her mouth. I deflected it and just talked with her instead. I dunno, but it felt kind of good knowing that she thought she couldn't make me cum. After all, a slim woman her age, still has A LOT of power in being able to just go online, tease and reject men, and still get casual sex whenever at the drop of a hat. I suppose that it just felt nice in the sense of putting into perspective how she's way past her prime and not all that at the end of the day since some (most) women tend to get offended when a guy cannot cum/get hard for them. Anyways, we talked for a few minutes more until I dropped her off at her home.


Not particularly proud of this lay, for obvious reasons (age/non youthfulness), but I guess from time to time I can reward girls that chase me. At least it was fast with very low cost/effort and I was wise enough to cover it up. Give to give.

S, the 41 year old Cafe Manager

S and I bantered over the phone and through txt for a good 5 days before meeting. My plan was to invite her straight over without meeting her out, and in order to do so, I knew I had to build some fairly strong rapport with her - I basically told her how I was not into dating and how I would just like to hang out in a casual manner. 

Leading up to the day we had set, S would throw out subtle tests of how I should meet her out instead and how she was not sure about it all. I held my composure and stuck to the initial plan of her coming over to check out the place and drink with me, all while giving her enough space to think about it and not push her into doing it.

The day arrived. That morning she txted 'good morning (my name)' and I responded with the address and time she should be over and left it at that. A few hours before she again tried bluffing and testing to meet her out, but I ignored it until the txt came in: 'on my way'. She took a Lyft and I would see her at last 20-minutes later around 8PM. I greeted her with a hug and told her to follow me inside. 

She looked younger/more youthful than her age - if I were a guessing man and had seen her in the streets i'd have guessed mid 30's. Anyhow, I thought she looked better in person than her pictures and was quite surprised really that a girl of her looks would come to a strangers place without being taken out. I suppose her being that age and fresh off a long term relationship called for somewhat desperate times with a guy who wouldn't talk her out of doing what she was likely in it for in the first place. 

I showed S around the place, kissed her in one of the rooms briefly, then she took a couple shots of tequila. I told her I had taken some before she had arrived, even though I didn't, just to make her feel more at ease and as if I was on her level - simply, did not feel like alcohol that night. We settled down around the kitchen. I sat somewhat far from her and we talked. She then came over closer to me and sat down, touching/patting me here and there, which was obviously an invitation to her warming up to me and being ready to get more physical. I then stood up and grabbed and made out with her and led her to the couch. 

I fingered, rubbed her pussy and banged her doggy style and that was that. She was really tight and my cock felt nice and snug. Me wanting to not fuck her without a condom, however, was the buzz kill and turned her off completely to where she put her clothes on shortly after I had busted. S was not on the pill and still wanted me to cum in her freely which I declined for obvious reasons. She already had a 20 year old daughter, and later told me she would have another baby if she could and that she would like to try within the next two years. She was brutally honest, which isn't a bad thing, in perspective.

S called for her Lyft and we hung out for another 35minutes until it arrived. At points it was awkward because sex had been so fast that it was like wondering what had just happened since we were already back to where we were before, all clothed again. She kept saying how she wished I had not worn a condom and how we can fuck again before the Lyft got there (as long as I don't wear one obviously). We walked outside and I gave her a hug goodbye as she got picked up. It was cold out.

She was cool/nice/sweet/easy going, but I did not like how much she wanted me to fuck her without a condom obviously. Big red flag.

M, the 26 year old talent agent

I met up with M on a Thursday night for a round of drinks around 8PM. I could tell going into it from her actions ahead of time that she had a higher interest level in me than average ie. she was the one putting in more effort by making sure I was free that night and checking up that I was still coming. I arrived 15 minutes after her. She worked fairly close to the venue and as a result was already half way down her first margarita.

M was 5'0" with a clear skin, jet black hair, green eyes, a nice smile and cute face, but unfortunately had fooled me by posing in pictures where she looked thinner than in person. I gave her a hug when I got there and we sat and talked about random stuff. Basically the stuff I always usually talk about on first dates to note how much she is into me, while at the same time checking up on her body language. She was very touchy feely and put her hand on my knee many times, leaving there for seconds at a time. I touched her too sometimes, but clearly this girl definitely dug me.

After she ordered another margarita and I was finishing my beer. She offered to get the bill - we had a running inside joke earlier on how drinks would be on her since she had closed a big deal that day at work. We finished, she got her car from the valet lot and dropped me off at my car a couple blocks away.

As we were nearing, I told M to pull over. We made out, I began to get hard, so I put her hand on my pants to feel. Then I made her reach down further until she unzipped them and began to go down on me. I then started fingering her hard until she eventually squirted all over her car seat. I was pretty surprised. It was too bad we were somewhat far from my place, but she ended up sucking me off some more after until I blew a load in her mouth and she swallowed it. Good girl. We said our goodbyes until next time.

M txted and initiated all the txting from then on until we met up again at the end of the week. She called too and wanted to talk on the phone at least once a day. You would think we were already a couple by how much she liked me already that even I was feeling unsure about the situation and how she would be a stage 5 clinger very soon.

She came over that Sunday. It was straight forward - she sent some nudes and a masturbating clip of her the day before. We went straight to my room, I turned on some music, we took some tequila shots and got straight to it. Banged her in missionary, doggy and she wanted me to cum on her face so I did on the second go after she had sucked me off. She even let me take a picture of it and was hinting at me filming it too if I wanted to. A picture was enough I suppose. Snap. She left just before midnight.

The next morning I woke up to a couple txts about how much fun she had and her wanting to know what my week plans were like and what I was doing for the Super Bowl weekend. I told her and left it at that without sounding too apprehensive.

The next day I told her we needed to talk and she called me and I told her how this was moving too fast and how we should take a break ie. my way of telling her that it was fun, but fucking her once was enough. She got the hint and as a result was mad, but i'd rather it have been done when I did it than down the line when she'd feel even more attached. So instead of wasting each others time with something that would never be, and clearly was her ultimate goal of locking me down to some sort of commitment, I had to do what I had to do.

Hello, 2015.