Escort turned out to be someone I knew
 

Well, I just had an unusual experience. I had an appointment for a massage (erotic, not therapy) with a provider who was well reviewed in TER and met several criteria that Seek when I'm looking for sex with an escort.

When I showed up at her incall location, "Lindsey" turned out to be a young woman named Carolyn who lives with her husband and two kids across the street and two doors down from me!

To say we were both surprised is to put it mildly!

I would actually find that fucking horny.

how did it go?

And hilarious at the same time. A very confused boner

Don't stop there! What happened??? :D

YEAH MAN WOW!!! You can't leave us hanging

When “Lindsey” came into the room and shut the door I turned around, we both said the same thing at the same time: “Are you kidding?”

Standing in front of me in a very short, very sheer teddy and a matching thong, was the late 30’s -early 40’s mom who lives across the alley from me! Now, I have always admired her: while she is not classically pretty, her face is very attractive, her voice is perfect, and her body is sexier than all hell: tall, slender with dark gorgeous hair and a moderate chest. I would be lying if I haven’t undressed her with my eyes from time to time.

I was stunned: Michael and Thomas’ mother -Joe’s wife- was standing in a see through outfit, planning to suck and fuck a new client. And I suppose she was having a hard time squaring the man in the wh*r*house with the neighbor who plays catch with her boys, has beer with her husband, and generally is just a decent neighbor. I swear it was a good 60 seconds before either of us moved or spoke.

I finally said, “Well, I won’t ask you what you’re doing here if you won’t ask me.”

She said, “I’m so embarrassed I want to die.”

“All things considered”, I said, “ You don’t have anything to be embarrassed about. If it weren’t finding what I was looking for on TER, this wouldn’t have happened, so there’s nobody here in the position to act like there’s something wrong.”

She said, “I can’t do this and then see you at home and act like it didn’t happen. This is bad enough as it is. But if you want, let me get you someone else.”

Now I will admit to being mortified, but I also wanted to get laid. And now I wanted to fuck Lindsey, whose real name is Carolyn. “Look, Carolyn, I think the genie is pretty much out of the bottle. You know I pay for sex, and I know you have sex for money. Obviously I don’ think that makes you terrible, and just as enviously you don’t really have a problem with men paying for sex. I don’t think we’re going to forget that. On the other hand, I see no reason to think of you any differently that I ever have when I run into you elsewhere. So just relax.”

“OK”, she said. “You’re right, I guess we can’t unring that bell. But there are other girls here: let me get you someone else.”

She was reaching for the door, as I said, “Please don’t. It would have been a fantasy for the hot neighborhood MILF to be a sl*t. Well, here you are. I LOVE that you’re a wh*r*. I want to fuck you a lot more than I wanted to fuck “Lindsey”, if you know what I mean. Stay. Let me see you naked. Suck my cock. Fuck me.”

“Alright. On one condition. We NEVER talk about this anywhere but here. This is the only place and the only way we have sex. This can’t turn into an affair.”

I laid the money on the table, and then had a GREAT time.

Have you been back to see Lindsey/Carolyn?

Ha ha..I think that "alright" from her was there from the start in her mind..she jus wanted it to seem more like your idea..lol

Not yet. Oh, but I will. . .

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.