Sunday, February 22, 2015

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.

Thursday, February 5, 2015

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.