A Classic Pick-up Story from My Archives

I’ve been getting a bunch of requests for some pickup stories lately. I used to write a lot more back on my first Myspace profile- before it got deleted. I had a bunch of good field reports and stories there. I was looking through my second Myspace profile and came across a good one that I never posted on here so I thought that I would post it…

This story was called “The Return of a Pickup Artist” as it occurred during a point in my life I was going through a minor slump socially and professionally. The story was original written in two parts. For sake of space I’m only going to copy part 2 here as that is where the majority of the action takes place. But part 1 contains the buildup, and is a fun read…to fully appreciate the following story I recommend you read it. You can read Part 1 here.

Return of a Pick-Up Artist (Part 2) by Bobby Rio

11:45 am

The day began with a Powerbar, vitamins, water and a cool shower. I contemplate putting in a few hours at the office. I quickly scratch that idea. I throw a pair of jeans on and head to The Saloon for a beer.

12:30 pm

I am not the only one in the bar. Apparently there are other people who use Memorial Day weekend as a way to justify drinking in the afternoon. I make a friend with a guy next to me. He enjoys the hot tub story. He tells me if it was him he would have fucked her. He is almost 70. Now he wants to tell stories. Here is some advice; never show even the slightest sign of interest with old people. They will take it as an opportunity to spend the next two hours spilling their guts about a life gone by. He is approximately the 600th old man in a bar who tells me not to get married. I am afraid that these old men have subliminally installed that in my brain.

12:50 pm

I decide that I do not want to spend my Memorial Day weekend with the kind of people who drink alone at the town pub. I call Gloria. Yes, I can hear the people out there saying, But you only got her number last night Bobby. Dont call so soon. These people have watched Swingers too many times. It is a great movie, but if you wait six days to call a girl after you get her number chances are she forgot you, buddy. The truth is when you get good at this shit you start writing your own rules.

12:51 pm

Gloria answers. She knew it was me. An indicator that she already put my number in her phone. We chat for a few minutes. I hang up the phone and smile. I wonder how she is going to be in bed later.

1:15 pm

I call Phil. He is finally back from Vegas. He tells me he thinks one of the hookers out there gave him the clap. I tell him he should give it to Penelope. Tell her you brought her a gift back. I get directions for some land up in Warren County that he wants me to do an appraisal on.

2:30 pm

I pick up Gloria. Here is a hint. For your first date with a girl don’t go the standard coffee, dinner, drinks route. She has been on that date a hundred times with a hundred guys. No, if you want to fuck her the first night, unless shes a complete slut, you’ll have to be a little more creative. Gloria is taking the ride with me up to Warren to help me assess Phils uncles land. She had a little bit of the hippy chick thing going on and I though this would be a good way to get her juices flowing. Who knows, maybe even fuck her in the woods.

3:00 pm

I have been in the car with her for thirty minutes and I have to say its been a pretty pleasant experience. I had put quite a few down at Bobs party and was a little scared I might get a surprise when she answered the door. But she is actually even hotter than I imagined. Shes got long wavy brown hair. Just kind of has that natural no make-up kind of beauty. Shes got to be in her late twenties. Maybe even thirty. There is a slight hint of age twinkling in her eyes. Its sexy though.

3:35 pm

I have been doing a good job juggling the conversation between PG and R. Every time I guide the conversation to edgier topics she bites right away. Then I steer it back to neutral topics: work, friends, family, pop culture gossip and just when the conversation hits a lull I throw out things like: coworkers who fuck, the first guy she kissed, when we lost our virginity, what celebrities wed like to screw and just when I sense the conversation has gotten too racy I bring it back to PG. Every time I bring it back to R, I test her out and see if I can elevate it even further. Each time I test her she bites and brings the conversation even racier. Soon she is describing the first time she gave a guy road head. I started seeing this conversation going in a very good direction. Unfortunately we were about a minute from the land. I did not fret, if I blew my load this early the rest of the day would be a waste. Here is another hint. The older the girl the more willing she is too elevate the conversation. Younger girl tend to be more naive when it comes to talking about this kind of stuff. The older ones eat this shit up. They are just as horny as you are, and have very little tolerance for banal talk.

4:00 pm

Phils uncles land is really beautiful. It is pretty barren, actually. There is a tiny lake. There are only a handful of trees scattered around. There is a small abandoned barn looking house. I walk around taking pictures. I jot things down, although this is only to make this trip seem a little more important. Like Im a real professional under my bad boy exterior. She sees through my bullshit and calls me out again. “Oh look how cute and professional you look.” Which was actually the look I was going for, but she said it with the slightest hint of sarcasm. I put my clip board down. I pulled out the camera. I told her to pose. That way all these boring pictures of barren land will have something interesting to look at. I had her posing all over the place in all kinds of positions. Fully clothed unfortunately. I contemplated going for a naturalgirls.com photo shoot, but ultimately decided against it. As cool as she seems, suggesting something like that could freak a girl out if the rapport isn’t as strong as you imagined. This early in the day I was not going to take that chance. There will be a time for that later.

4:15 pm

A pack of wild sheep stroll in from the field in the back of the property. The look in Glorias eyes when we see the sheep let me know that the juices are officially flowing. I start snapping some pictures of them. Some girls just get so damn turned on by nature. The kino has begun. All day hands were always brushing against each other, I was not shy about touching her but now the touching was turning flirty. Hands were getting left places longer. Rising higher lower. All the signs of an adventurous afternoon were there. She suggests that we check out the inside of the barn/house. I wonder if there is an abandoned bed in there. Boards are over a door. Here is a hint. Use random opportunities like this to display some alpha male characteristics. I dont mean be a meathead, you just have to do those certain things women like to see men do. Caveman type shit. Displaying raw power. So instead of giving up when I saw the bars over the door, I made it a point to bust the fucking door in. It took a few times and knocked quite a bit of wind out of me, but we got in that house/barn. I grabbed her hand and we walked around for awhile. There was a bed but it was decrepit looking and Id have preferred the floor.

I saw a room in the back that I decided would be the room. I got behind her and guided her toward the door. I joked with her saying that someone was behind the door waiting for us. She grabbed a hold of me, as planned. Once you are at this stage use any excuse you can to get her touching you. I kept nudging her toward the room chatting her up about the crazy ax man behind the door. She kept getting closer and closer to me until I could feel the warmth from under her jeans. We finally pushed the door open basically falling into it. To our surprise though three hawk like birds came flying at our heads. It was definitely a buzz kill. My racing heart and freaked out gestures definitely subtracted from some of that alpha male I had displayed earlier. Oh well, I have a fucking fear of birds. What can I tell you? Luckily she was even more freaked. She quickly pulled me out of the room and out of the barn. I ask her if she left because of the birds. She says sort of. She left because if the birds hadn’t of come she was about to do something I probably wouldn’t respect her for tomorrow. Shes right, I probably wouldn’t have. I don’t say anything though. Another hint, when a girl throws out a comment like; shes not going to sleep with you tonight because she likes you or because you wont respect her in the morning. Ignore it. Dont respond with anything. A lot of times girls are just saying this shit to make themselves feel better about what they are about to do. Let them rid themselves of the guilt, but dont make the mistake of joining in the conversation because it wont lead anywhere good.

4:45 pm

We are in the car on our way home. There is less talking then on the way up. The silence is not uncomfortable. Dont always feel the need to keep the conversation going. If the rapport is good enough you can enjoy the silence together. Give her time to think about how cool you are and a whole bunch of other reasons to justify fucking you later.

5:30 pm

We grab a quick bite to eat at a small Italian cafe near her house. Our hands are in the middle of the table intertwined. She has gone googly eyed on me. Normally this look scares me, but she just has this confidence about her, such a sexy at ease way, that I found myself a little flattered by the adulation. She is looking at me hard. She runs her hand through my hair. She tells me I should let her cut my hair. I ask her if she doesn’t like my hair. She gives thumbs down. Then she laughs and says, Just kidding. But she would like to cut my hair. I am genuinely enjoying her company. Just thought Id throw that in there so that you don’t think the only thing on my mind is sex. Yes, Bobby is all around pleased with this one and gives her the Bobby Rio seal of approval.

5:50 pm

We are in the car on the way to her salon for a haircut. The place is closed but she has a key, and is basically manager of the place, so no one will mind. While Im perfectly happy with my present haircut, when I was a little kid I used to get so turned on when the shampoo girls breast would brush against me during the wash that I couldn’t resist the idea of sitting in a chair watching her in the mirror. In the car ride I bring the conversation back into R territory. I ask her if she gets turned on by the toe polish scene in Bull Durham. She asks me if I want a pedicure at the salon. I tell her I have a foot fetish. I cant tell if she realized I was kidding. But the bait worked and she telling me about a scene in another movie that turned her on.

6:15 pm

I am sitting in a chair at her salon. I have towel choked around my neck and a restricting smock on. This is not as sexual as I imagined it would be. She leans my head back into the sink and I wince when my neck touches the cold stone of the sink. I look up and she is soaping up her hands. She runs water over my head. She keeps touching the water and asking me if its warm enough. Finally her fingers start running through my hair. I want to open my eyes and look up at her. She is sexually massaging my scalp. She leaned into me and a titty brushed against me. I am aroused. I wonder if I should try to hide this fact or leave it out in the open and see if she catches it. I decide fuck it; and dont adjust. This rates up there with a scalp massage I got from a pro in a termas in Rio a few years back. No joke. I came from that scalp massage. Now Glorias massage was not going to make me cum, but it did make me pitch a tent with my smock as I got up to walk over the other chair for the haircut.

6:17 pm

The hair cut has begun. I watch hair falling off my head. I wonder if it will make things awkward if I hate my hair cut. I mean how am I supposed to act if she really fucks it up? My attention is quickly diverted from my haircut to the mirror where I watch as all of her attention is focused on my head. I appreciate the enthusiasm in which she is doing her job. Which makes me wonder if I should tip her when shes done? I decide she will get a tip. And then the whole thing.

6:19 pm

You are so fucking sexy, I tell her and really mean it. When you say something like that to a girl; say it with all the confidence you can muster up. Make her feel like the luckiest girl in the world to hear it. One good compliment can melt away any defense she might have still had up. As soon as I say this she drops the scissors. I spin myself around on the chair so that Im facing her midsection. We stare at each other for a second, and then I pull her towards me. I smell her neck for a second and then turn her face toward me and start kissing her. We are making out hard.

I have no fucking clue what time it is pm

I stand up and push Gloria down into the chair. I get on top of her and am kind of grinding into her. She is extremely turned on. I am extremely turned on. She says we cant do it here, people can see in. Just when I think Im going to have to overcome another obstacle, she suggests we go into the back room.

At this point I am about to indulge myself in the details, as they are fond memories. If you are uncomfortable reading about my sexual exploits you probably shouldn’t continue.

In the back room there is a recliner chair where they do waxing and stuff. I lay her down on the chair. She cant pause for a minute. She pulls me into her. My mouth goes back in forth from her mouth to her neck. My hands are running up and down her legs. I tease with crotch rubs. The unbuckling begins. My mouth goes down to her belly button area. I help her with her pants. I watch her wiggle out of them. No panties!!!! God I love hippi girls. Shes got the trademark hippi girl patch. Just enough muff to keep with the natural girl image, but trimmed up enough to still look edible. So I eat. She goes crazy.

I sense that she has come from the oral. She turns me over and is practically ripping my jeans off of me. I do the lean back please me lean and await my reward. She goes down on me and I am enjoying it way too much. I pull her head up and tell her again how fucking sexy she is. Another hint: That was only the second time I complimented her all night. Use compliments sparingly so that when you finally give them they will be regarded higher.

I wiggle my boxer briefs from around my ankles stand up and push her down on the chair. I am inside of her now.

This is truly some of the best sex Ive had in awhile. There is a glorious finale with an extremely satisfying cum. We are both breathless. Hint: Guys even if shes the fuck off the century dont get all gushy telling her how good it was or how much you like her. Lay there, put your arm around, cuddle like youre really into (it helps when you are) and be fucking silent. Trust me words are not necessary.

8:30 pm

I drop Gloria off. I know some guys would have asked her to spend the night. I easily could have spent the rest of the night with her. I was really enjoying the time with her. But you really have to wait to see where you want to go with this before you start getting so close. If in a week you decide youre not into them it is easier to start blowing them off. As much as I am into Gloria shes a little old for daddy and probably wont make the cut. But well see…

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About Bobby Rio I'm Bobby Rio, one of the founders of TSB. I tend to write about what is on my mind so you'll find a mix of self development, social dynamics and dating articles/experiences.  For a collection of some of my favorite articles check them out.