I don't know. She was really pretty uptight. The I first got undressed noticed that she was looking away. I finally said to her, "Look, relax. this is going to be fun and we are going to have a GREAT little secret. I know it's just business for you, but I really love the rush of fucking relative strangers. You're no stranger, but this is a very different kind of exciting. So think of it like this: you get a client who you know won't hurt you and isn't a whack job. And I'm not going to tell a soul."

She said, "I'm OK, it just takes a minute to get used to the idea. But you're right: I just get a client that don't have to worry about." She kind of cocked her head and with a little bit of a laugh fell back on the bed and said, "So do me stud. Fuck my pussy."

We had a good time, but she did take some convincing.

Love this....
 

I’m gonna be following this story. We would all love to hear the play by play if you could be convinced to share it. I’ve never paid for pussy but I for sure wouldn’t be opposed to it. Keep us updated!!

Sorry Dinger67, but I have to disagree with you. If you got pussy, you paid for it in one form or another, dinner, time, flowers, jewelry, gifts, etc.. Sometimes cash is the best way. It's just a contract, I fuck you, and you leave.

ABFRH,
While it is rare one of my first experiences was truly free. I was a Sophomore and was in class when I was propositioned by a gal in class regarding a blowjob. She wanted me to meet her in the mat room in the gym. I told her not likely as I had team tryouts at the end of the day. Well on my way to the tennis courts from the locker room I passed by through the gym when she cornered me by the mat room and pulled me in. Gets my shorts down and gives me a quick 15-20 minute BJ and never misses a drop. Pulled my shorts up with a zip and a clip and off to the courts feeling on top of the world. On my way back to the locker room and showers I run into her and we make out a bit and I slip it in through the leg of her Dolfin shorts with her panties pushed aside and her leaned up against the Universal rack. This did not last long as her underwear was cutting into me. She met me in the lower parking lot after i showered. She took me back to her parents place where we made out a bit more. She was definitely the aggressor in our relation for about a year as we did not make it through two Christmas'. It was great while it lasted and we even hooked up later at Uni.

Carolyn aka Lindsey no longer works at that incall location. A few weeks ago, while I taking a walk, we passed each other and stopped for a brief, discrete chat. I told her I'd like to see her again and asked when she would be at work next. She told me the place closed after back page went out of business. In the course of the conversation I asked her if she was going to continue doing massage. She told me that it's the only way she would do the work, since she could could control how far she went when the premise was massage. But she also said that it was extremely difficult to work with no means to advertise.

I told her I really needed one of her massages and asked if she'd make a house call. She told me there was no way she would come to my house, since she can see hers from mine. "THat's just too close." I asked her if she had ever encountered anyone else from the neighborhood while working, and she said she had never run into anyone she had met in, as she put it, "real life". I told her she was, then, just being paranoid: if she were entering or leaving my house, no one would think a thing of it, any more than they had on the many occasions when she'd stopped by to borrow something, or to ask a question. I told her that id she just came over in dressed as she commonly is -jeans and a t-shirt, it would look perfectly normal. She agreed to come by in an hour with no promises whether she would follow through

-and???-

That request of mine several months ago was not fulfilled: she did not stop over. Since then I have not pressed the issue, and I have run into her several times at around the neighborhood, with the conversation never returning to the subject of her former work.

Last Sunday neighbors had a "garden party" wedding reception for their daughter. Carolyn was there as were many other neighbors and 100 or so people I've never met. The party went on for hours and I paced my drinking carefully since I didn't want a hangover. As things wound down and people were starting to leave, I saw Carolyn walking very unsteadily. As she approached me she asked if I would give her a ride home. I toid her that I had walked and since it was only a matter of a few hundred yard to my house and a few hundred more to hers, I would be happy to walk her home.

She was not sober, but certainly not sloppy drunk either. We chatted as we walked and I finally asked her if she was working again and she replied that she was not. We were near my back gate at the time, and she pulled me over toward it and said, "open this thing". I thought she was confused in her inebriation and said, "Wrong gate. That's my house." She responded by saying, "I'm drunk but not so drunk that I'd fuck you in my yard. I know it's your gate."

I opened the gate and asked if she was sure. The last thing I needed was a sober woman to regret what the drunk woman had done and turn it into a problem. She tugged me over to the side of the gate where the fence line is hidden by a very tall hedge, and said, "I will be after we shower" as she leaned into me and rubbed my cock through my slacks.

I took her into the pool house and left her to shower while I went in the house and grabbed some towels. I came back an stripped to join her in the shower. After a bit of wet play, we stepped out and dried off, and I suggested that no one could see us where were and the gates were locked so we could just stay out on the pool deck. She sat on the edge of a chaise and I got a view of her leaning forward, tits hanging down and legs somewhat splayed, that I will remember for a while.

Because she had been adamant before that we would not see each other away from her work because she really didn't;t want to have an affair, I took the time to mention that to her and to tell her that just to keep things on that basis I would put a donation for her on her chair. She pulled me over and said, "I still don't want to have an affair, but the only donation I need is your dick. I need to get fucked. You're elected."

I don't know if I'll ge too do that again, but it sure was a good way to spend an evening.

Very HOT!!!
 

Enjoying your posts. Have to admit that the thought of fucking the hot neighbor MILF is an absolute turn on.
I do have two questions. Does her husband know about what she did/does? And because she knows you on a personal level does she fuck you bareback and let you cum in her?

Absolutely true, ABFRH. Those who don't pay for it before, pay after!

Her husband certainly doesn't know about me and I don't know if he was aware that she her massage work involved fucking, but I really don't know.

As to condoms, she the first time I saw her she used one for everything at first, but then sucked me off without one. I have never fucked her bareback.