Paying for it: Volume 1- Helping a friend [m/f]

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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Well on to the first instance…

I was in college and the Internet was just getting mainstream. Using telnet to connect to other university computers and chatting with other students there was something only a few people were really doing but it was going on. I got to know a student Anne, from a nearby college and we hit it off well enough to have a meeting for dinner and a drink to see if there was any potential. We hung out for a day and though there was some attraction it wasn’t enough of a spark for either of us to parlay it into a full dating situation. However we remained friends and chatted regularly. Over the months ahead. Even though we didn’t even kiss at our hangout meeting we eventually got to discussing sexual topics, because that’s what you do when you’re in college, especially if you’re going through a dry spell.

Eventually she got to her pride of how well she gave head. How a few people including her guy she’d just started seeing said she was the best they ever had. I said that’s something to be proud of and left it at that.

Cut to a few weeks later and I’m chatting with her online in the library, just checking on how she’s doing and she says not good. I’m trying to be supportive and ask what’s wrong and she tells me that she had some things come up and she’s going to be short on her phone bill and was worried about late fees and the spiral of bounced checks she was worried was about to happen. I asked if her guy could help her and she said he had already helped her and lectured her on being better with her money.

Now a little something about me. I’ve always had a talent for having side businesses and ways to make extra cash through short term contract work or odd jobs etc. Even in college I was attending without loans and had some extra cash. I asked her how much she would need to be in a better spot till all the bills came through. She told me $50. I said I could help her out with $50. I could even drive it up in the next day or so. I asked if she knew when she could pay it back…

Now I was prepared to just give her the money if she just said she wasn’t sure she could. But what she said instead changed everything. “Could it be tomorrow and could I just blow you for it?” I sat stunned staring at the green letters on the black screen, *yes I’m old* , hardly believing it. “Are you serious?” I replied with the hard clicking keys seeming louder than usual. “I am. but it has to be tomorrow. My boyfriend is out of town and my roommate will be gone too. And no one can ever know.” *Guess I’m breaking that now.* I hastily agreed and we picked a time I’d come to see her the next day. I stopped by the atm and got the cash with a little to spare and made ready to drive the next day for this adventure.

That night I couldn’t sleep. I was very excited knowing I had a sure thing tomorrow. I wouldn’t be rejected. I would get what I want on my terms and so would she. My heart raced thinking about it.

The next morning I was on the road having called on the way. She said her room was clear and she was ready and to make sure I had the money. I did and soon I was greeted by her outside her dorm and hurried in so that no one would ask who she was with. We got to her room and she shut the door and it seemed she hadn’t really thought all this through. I complimented her on how good she looked in the top she had on. I asked if she would take it off. She said she hadn’t planned on it. I made a slightly disappointed face and she paused and said 10 more. **Deal!** I got out the 60 and laid it on her desk. In that moment there was a feeling of power in that this woman who thought I was a nice enough guy but not dating material was going to be willing to be sexual with me because of money I had made that I was willing to give. It would short circuit attraction and regular rejection and get me what I wanted from her, something I didn’t think possible until she offered it.

She removed her top and her curvy breasts bounced into view. I reached out and touched them with my hands. Seems that was covered by the 10 without being spoken. Her nipples hardened as I teased them with my fingers. I leaned to try and kiss or lick one and she stopped me. “I’m on the edge here. I know I shouldn’t be doing this. I know it’s wrong. I know I’m risking my boyfriend if he found out. *She never brought up it’s illegal* But I need the money. Could we move this along while I’m still able to do this.” I didn’t want to see her have a breakdown or change her mind so I agreed. Then she asked if I’d place the top she had taken off over my face so she could pretend the situation was something other than what it was.

Now any other situation where a woman is trying to not Think about who they are with would be quite insulting. But in my mind I was going to get my cock sucked by a woman who wouldn’t under normal circumstances so I just agreed and readied myself by placing her top over my face and waiting.

I felt her nervously undoing my belt and removing my shorts. My boxers soon followed. The whole situation was electric for me. My inability to see heightened the sensations. I felt her grip my cock and stroke it a little. There seemed to be a very long pause and I wondered if she was about to back out. Then I felt the warm wetness of her mouth begin to work the tip. I groaned and arched my back slightly.

Tentatively she began to do more. She twisted her head. She began to stroke what wasn’t in her mouth with her hand. She popped off and turned her mouth sideways and worked the underside of my cock up and down. This had me gripping her sheets and bedspread hard. Then she tongued my base just a little before returning to sucking me with her fist pumping underneath. “That’s so good. You weren’t lying” I groaned bringing up her previous bragging. She gave a muffled “fank you” then doubled her efforts trying, I suppose, to speed this event along.

Generally at that time in my life it took a while for me to cum from oral and that day was no different. She worked up and down around and around. She licked and pumped and deep throated working to get me to cum most likely so she could move on from this moment in her life. Finally I felt it beginning. The build up was on. The shivers were going through my body.

At this point I realized we had never discussed spitting, swallowing, etc. I warned her hoping she would sort it out. “Anne I’m about to..,” I began to pant. She stroked hard. She sucked harder. Her tongue was wriggling under the v tip between plunges up and down then my hands moved over her head as I shot one of the biggest loads from that time in my life deep
Into her mouth. She struggled a little and then pulled off of me. In my daze I didn’t pull the top off my face to know if she swallowed it or discreetly spit it in the trash as I was basking in my post orgasm fog. She pulled the top off my face and thanked me for helping her out. I thanked her more.

The goodbye was strained and I had a feeling this would be our last time talking. She would message me back less and less. I never asked for it to happen again and she never did either. Eventually we lost contact but my fuse was lit. I sometimes wonder if she had done that before or ever did again or if I was her only “customer”. I do hope it wasn’t scarring. I hope she’s happy wherever she is. As for me. There are other adventures that are much more intentional in searching for pleasure and being willing to pay but I’ll have to write them later.

Source: reddit.com/r/gonewildstories/comments/4aon75/paying_for_it_volume_1_helping_a_friend_mf