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.

M, the 18 year old college dropout on sui watch (11/2014)

M contacted me with a simple "Hey" around 10pm on a Monday night. Now receiving any type of message at that time and beyond you may think a girl would be up to meet right then (and there and be dtf at that), but that was not the case with M...yet. We really didn't talk too much. Her profile said she liked to blaze and had a past in web cam modeling, which was enough for me to get a sense as to the type of girl she is ie. non prude. I didn't push to meet that night, simply left my number and she didn't txt so thought was a lost cause until a couple days later when she wrote again and I responded simply with a "let's toke".

When I sent that, I had not blazed in close to 6-months, and even then, I rarely did it. I made a call to someone I knew that night that was in the area and picked up $15 worth right after agreeing to meet up with M at her parents house before noon the next day.

Woke up the next day, went to the market and then called M to tell her I was on my way. Going into it I felt a little uncertain. Both of her parents worked and her sister was at school, yet she told me that she doubts her dad would be home, but just in case, I'd be able to hide in certain parts of the house. Gee thanks. Made it to the door, rung it, greeted her with a hug and told her I'd left the weed in the car - my way of cautiously checking out the surroundings before proceeding. Better safe than sorry, I thought. I mean how many 18 year olds will meet a stranger in the middle of the day when there's no one home? This was not your average 18 year old.

After giving me a tour of the house, we went out in her backyard, grabbed a seat and started to smoke and talk about life - we situated ourselves in an area where we could see and hear if anyone was home. She told me how recently in the past week she had moved back home after dropping out of college due to a medical leave. What kind of medical leave? Suicide. She tried just last week, while still attending, to end it all. It wasn't her first time, she told me. Other than that, she also told me that she had a sugar daddy before moving away to college. Right - definitely not your average 18 year old. Or are they more or less like that nowadays? Anyways, trying to space out the rapid amount of details she had just told me, I decided to concentrate more on the hits I was taking and how I was feeling right after each one. I then kissed and made out with her a little bit before taking a couple more hits each, all while having her suicidal tendencies and slight chance of her father coming home lingering in the back of my mind.

I got up after we were done, signaling to go inside. I told her 'let's watch TV' and she said we had to go to the one in her room upstairs because she couldn't figure out how to really work the one downstairs. Upstairs we went. She had some weird series on that she had been watching reruns of on Netflix. We sat on her bed. When she pressed play on her 'favorite' episode, she said how the intro is really long, where I then told her that we could do this meanwhile and pushed her on her back and continued making out until the intro had settled into the storyline. She told me a brief synopsis up to this point in the series and pointed at her favorite character. Within 5 minutes into the episode, my hand was down her pants.

I fingered, choked (told her to tap out if it was too much for her) and rubbed M for a good 10 minutes until I felt she had had a good orgasm. I put her hand for her to feel my hard dong in my pants in which she was quick to unbutton and put into her mouth. While she was giving me head, I kept rubbing her. Had to actually tell her to slow down because she was going quite fast and I did not feel like unloading yet. She then maturely said, "don't you want to fuck?". "Sure," I said, proceeding to put a rain coat on. 

M was really tight and I loved how pink her pussy was and how there was not a hair in sight - was this close to eating her out, but my judgment said I better not. We fucked missionary, doggy and she got on top of me and did the reverse cowgirl - she seemed to really like how I pulled her hair and slapped her ass while fucking her in doggy. I blew my load and then rubbed her some more for 5 minutes. Round 2 I decided not to wear protection - call it risky with a girl like this - I blame the weed. We fucked some more until I finally pulled out and came on her stomach. Being the sly gentleman that I am, I went to the bathroom and grabbed some Kleenex to wipe her down. She appreciated that.

We then got our clothes semi-on and talked a bit more about what we're doing the rest of the day. She was going to some job fair and then seeing her psychiatrist. I told her what I was doing, before walking downstairs to the entrance, giving her a hug and telling her to let me know how the job hunting went.

She didn't do that, but she did send a "hey" again that night using the same service we had met on some days before.

J, the 35 year old movie studio interior designer (10/2014)

I sent J a simple, "You look great. (my name)" on a Friday night. She responded quite fast with a "Thank you. What are you up to tonight?" I responded with what I was up to and she said she was going out with a couple friends that were in town and that I should join them with a couple of my buddies. It was a bit late notice and she lived on the other side of town. No go that night, but we did make plans for a couple nights later.

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.

P, the 30-something techy (10/2014)

I found P from the popular app as well a couple days before my nite with Y. I semi screened her more than others and in the process found out she was on there looking for a 'new boy toy'. We exchanged numbers and made plans to grab drinks at the end of the week. She seemed really busy with work, yet on the odd night before meeting up, she'd reach out wondering what I was up to, sending me light sexual innuendo. I then proceeded to send a cock picture (not mine, but looks like it could be mine) that she responded well to - just another part of my arsenal that I use in the screening process sometimes.

As Sunday came around, we agreed to meet at at a bar a walk from where she lives. I stopped by the market before to do my weekly grocery shopping and then called her that I was on my way and was running a few minutes late. She was appreciative of me letting her know and sounded very sweet. This was two days after my nite with Y and I was feeling good going into it.

P was waiting for me at the bar. I greeted her with a hug and told her that she looked great. She was really silly and laughed at almost anything I said - weird, but cute. We ordered some beers and talked about travels and she told me a bit about her unique tech job. P was smart and quirky. She had a degree from one of the top colleges in the state and then returned later to get her masters. Now smart girls can sometimes be a drag and be ball busting, but P did not seem that way - for now.

We finished up our drinks and I told her I had to go. We walked outside and towards her apartment and my car. The vibe was weird. Could not read whether she was into me or what was going on. There we were on the sidewalk right as I was going to cross the street to get in my car. I asked her what she thought. She just laughed and said, 'well if you want to walk me home...'

I grabbed her hand and walked her to her apartment a few blocks away. At the lobby, she thanked me and was still acting strange, without hinting that she would like me to come in. It's basically as if she was dismissing me there and sending mixed signals. Somehow I was able to deflect some of these "well I think i'm too old for you" and "don't think i'm your type" responses and slid past the main door with her and headed in the elevator with her apartment shortly in sight. I felt like i'd just gotten away with something, as I passed her shit tests right and left.

Once inside. I complimented her place and even asked her how much she paid for it. She offered me a drink - which I obliged and felt I deserved at that point. She was on one of the top floors of the apartment complex overlooking a series of palm trees and the city brightly lit in sight. She grabbed me a beer and made her self a vodka redbull. I perched myself outside on the patio deck, where she would meet me and I planted my first kiss on her. P was a great kisser. She loved to make out and use her tongue to the maximum.

We drank our drinks outside and found out more about each other and how we shared a few commonalities in tastes in music. When I finished my drink and she hers, I headed inside to look around more and she followed close behind. We then settled down on her couch and I started to grope her as we made out more, this time harder - something she said she didn't really like and thought I was too aggressive. Okay, if I wasn't persistent and aggressive, I would have never made it up here. Could this girl be more of a tease/sender of mixed signals?

The last minute resistance was strong with P. One of the strongest i've had. She was fine with making out and all, but when it came to me trying to squeeze her ass, put my hands on her inner thighs and getting her on top of me, she would deflect and push them aside, telling me to not squeeze her so tight and to be more compassionate and slow. I tried how she said she liked to be held and began kissing slower. Still the cockblocking was happening.

It was around 11PM and I got up then and there and told her that's all I had and it was obvious she was not into me. Not in a bad way, kind of in a smirky kind of way as I told her it was nice to meet her and I was leaving. She walked me to the door and opened it for me. At the end of the hallway was a blond girl in her 20s walking towards us. I told P, "well I guess i'm going to try and get laid from her then".

Right then and there she grabbed my hand and brought me back inside saying, "i'm not going to let her see you do the walk of shame just like that. I feel bad". I closed the door and we made out again with my back against the door this time, focusing on being more 'soft' and 'passionate'. Before relocating to the same couch, she brought up whether the cock picture I had sent was really of me and whether it was just an angle. I told her it was me and then put her hand inside my pants so she could feel how hard she made me. I then unzipped them and she began giving me a hand job, not saying anything about whether it was not me in the picture or not. I, too, began to put my hand on her pussy, finally getting my hands down there, rubbing her good. She was ultra sensitive and it did not take much for her to orgasm and quiver while shaking her legs together in a moan.

At that point I sat up as she was continuing to stroke me. I then hinted for her to give me oral and pushed her head in a down motion in which she responded, "i'm not going to suck your cock". She did ask whether I had a condom or not however. I said I did. She laughed. I told her, "hey I carry it in my wallet just in case". I took her hand and relocated us to her bedroom where I strapped on and went to town slowly. She was really tight and I even had to apologize for going in too fast at first. It was at that moment that I could see her in her natural, submissive state, looking up at me - I was very turned on to say the least. We dirty talked a little bit as I licked her tits and thrusted deeper and deeper before I came.

It was a really hot night and I was sweating like crazy. She became irritated at me standing up next to the open window trying to get a breather, instead of laying down with her to cuddle. We talked briefly as I got on my clothes, cracking little jokes here and there.

I knew I wasn't going to see P again, and I wish her well.