First I want to thank everyone for the upvotes and comments on [Volume 1](https://www.reddit.com/r/gonewildstories/comments/4aon75/paying_for_it_volume_1_helping_a_friend_mf/). I needed a few days to get the next one written up best to my recollection and with typos and grammar addressed.
So I decided to chronicle a series of adventures in my life that I’ve had that had something in common, I paid for them. Yes look at the loser who paid to get laid. Well I didn’t set out looking to hire a woman for companionship. The first time fell into my lap if you’ll forgive the pun and from there it progressed.
**Now a few things to get out of the way.: yes I know this is dangerous: stds, arrests, getting robbed or worse are all potential liabilities. I have always worked to minimize these risks so please let’s leave the lectures out of the comments and PM’s.**
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So onto the next story…
It had been a few months since my encounter with my online friend from another college. I’d had some dating successes and some failures. In that time though I had started a habit, out of curiosity. When driving from one side of town to the other for work or to see friends, etc. I would detour so I could drive the local “stroll”. For those who don’t know the lingo and couldn’t guess, the stroll is the area of town that street walkers congregate so that gentleman looking to hire one can “drive through” to pick one up.
I started it kind of curious to see what types of women were walking in my area. I lived in a smaller town at the time but there was still a stroll in fact it had moved after the local media did a big story on it. Took some time but eventually the walkers and drivers figured out the street 2 blocks over worked well. So I’d veer off the path a few blocks and drive through to take a gander.
Now no idiot drives through opening their door for the hottest woman their first time through. That’s how one ends up on the 6 o clock news. I kept an eye out for girls I saw repeatedly over that time. There were some rough ones in not going to lie. I didn’t really have an interest in most but a few ones looked interesting. I kept going about my business of just window shopping over time and went about my life. Then I had a situation with a woman I’d been trying to go out with. She had been putting me off politely and not being direct. But was polite to a fault that it looked like she had interest and it just wasn’t a good time or she wanted pursued harder. Then a mutual friend told me the real score and I took it hard. Then all the feelings of what money had done to bypass rejection kicked in and the detours became more purposeful. I went looking for who would be my first truly “paid for” experience.
There had been one woman I had noticed a few times. She looked to be my age or younger, she has medium length curly hair, and she seemed to have nice sized “hanging” breasts judging by the tops she wore. I was a huge Christie Canyon fan. *Again I’m older.* I kept an eye on her seeing if she was walking in the more secluded spots to make a “pick up” easy as I was very nervous and not wanting to expose myself to legal or rumor trouble.
Finally one evening I was driving through and saw her in the perfect spot and it was almost automatic. I made the decision this was the time. I turned through an alley to loop back and stopped with the front of my vehicle just in view. She saw me stop but not get out and started approaching me. My heart raced. I reached over and rolled down the window. *Yes the vehicle was older too.* she walked up to that side. “Hey there” she said.
“Hi.” I said trying to choose words carefully and not make a move to spook her or me. “So what’s your story?” I asked trying to sound like if done this before.
“Looking for a ride.” She said smiling some.
“I’m looking for some fun. Wanna help each other out?” I replied. She smiles wider and opened the door and got in. We pulled away and my heart was a mile a minute.
“Hi I’m Michelle.” She git in with her hand in her purse. We talked as I pulled away and we somehow got laughing about something. I don’t remember what because of what happened next. She fiddled with her hand still in her purse and put her purse down. I looked at her questioningly and she said rather matter of factly. “I was putting my box cutter away, you seem a nice enough guy I feel safe.” This was a weird mix of scary as hell and what have I stepped into and wow this is for real.
“So what are you looking for?” She asked pulling me out of my stunned stupor. “Well, I asked what’s the menu?”
“Well, a Blowjob is 30, half and half is 50…” I showed my naïveté and asked what half and half was. “I blow you for half the way and you fuck me til you nut.” I nodded. “Or 80 I’ll stay for an hour and you can get all you can but I don’t do butt stuff.” I nodded and pulled over to an atm and got out enough funds to go with the little I had in my wallet to reach the 50. “The half and half sounds good. Won’t take long to get to my place.” She seemed surprised I said it. “Do most not do that?” Again showing how green I was. “Most just do me in the car.” She replied.
Not long after we pulled up to my place. It was getting dark now so no one would see and wonder who was visiting me. We went inside and I offered her a drink if she wanted it. She just wanted water. After that she asked if I wanted to do it in the living room or in bed. I led her there and she smiled at me and asked if I liked her. I admitted is driven by a few times. “Hmmm had a crush?” We both laughed and she sending my newness took her too off matter of factly and suggested I get undressed and on the bed. I did and my cock was throbbing as I laid down and watched her finishing undressing. Her body was a bit weathered from mileage but still looked good and her breasts were what I’d hoped for. Since I was staring at then she came over and dragged them over my face and I sucked on them slightly before she made her way down to my cock.
Now I’ve had blowjobs from women I’ve loved and they are special and had an intimacy that can’t be touched, however there is something about a pro that is different. Someone who’s next meal, rent, or fix depended on how well they give head. Someone who’s made a practice out of doing a good job so that her customers will come back again and again and she was one of those pros. She went it with light teasing until she sensed me get comfortable with the situation then the intensity went to 11. She plunged fully down and her tongue worked around inside her mouth before pulling back up and repeating. Then she stroked and went to work licking my balls with special attention. This was a first for me. Guess I had only dated non ball lickers to that point. It was amazing and I told her so. “I’m glad you like it.” She said before returning to her work. She pumped with her fist while swirling her tongue over the head. Then fully thrusting me.
Finally she asked if I wanted to finish in her mouth or grab a cover for the other half. I grabbed a condom and she took it from me. She rolled it down then climbed on top and lowered herself. She ground on my cock while again dangling her breasts in my face. “Feels like you needed this.” She teased as she started a slight bounce. “You need to be doing the driving?” She asked as her breasts bounced more and more and I enjoyed the view. “Sure.” I replied and she rolled over to the side.
Her legs hiked up easily and I rested them on my shoulders and started deep thrusts into this woman who was happy to let me have whatever I wanted so long as I gave her what she wanted. It was about my pleasure but she seemed to be having fun too. “Yeah bend me back and fuck me good. You need to cum don’t you. You need to cum in my pussy?” The condom was fully secure she just really knew how to get me worked up.
After a bit more thrusting I felt my body slipping to the point of no return. I started to breathe harder and harder and thrust faster. And she kept encouraging me. “That’s it. Cum hard!” And I did, gushing into the condom. I collapsed forward then withdrew and disposed of the rubber and we laid there and talked a minute. I asked if she had a number so I could call directly instead of cruising. Her beeper needed replaced. *once again. I’m old* but she told me where I found her was her usual spot. She was saving to get a place for other girls and her to work.
We got dressed and I drive her back to the corner and discreetly dropped her off. It wasn’t the last I saw of her and she certainly was not my last adventure in paying but as I went home and reflected on the fun vs risk considering the comments about the box cutter I figured too much street walker exploration could cause big problems. She’s the only street pick up in my history, but I’ll admit, I still enjoy the occasional window shopping trip up my current cities stroll.
More to come I can’t decide if I will tell of more times with her or other stories with other girls. I’ll see how I’m inspired.
Source: reddit.com/r/gonewildstories/comments/4bh9di/paying_for_it_volume_2_the_pickup_mf