[M]y [f]irst Craigslist experience

I work about an hour from home, so I have a long drive to work every day in the early dark mornings. Mostly country roads with few other drivers. Many times I have jerked off while driving to keep myself awake and entertained. Usually I’ll cum in an old sock and chuck it out the window. A few times I’ve even brought my fleshlight and fucked it while driving. No better way to start the day than with a powerful orgasm!

Well, I’ve grown tired of doing the work myself, and I make decent money now, so I decided to look at other options. Specifically, I’ve been looking on Craigslist for erotic massages and the like. There’s not much to choose from out in the boonies, but they’re around. Eventually I found a promising listing from a woman servicing guys out of her home. She required a quick meet and greet at a local Mc Donald’s before giving out the exact location of her house. So after emailing her what I’m looking for, we set up a meet.

I was pretty nervous for the next two days before the meet up. The day of, I was sure to clean myself up a bit to look presentable. I arrived at Mc Donald’s about ten minutes early and grabbed a booth in back away from the only other person in the place. I watched every car that pulled in until I saw one park and turn off the engine. My heart was racing as I waited to see her get out. The door opened, and out she came. She had longer dark brown hair, Latino skin color, just slightly thick with nice DD tits and a really tight plump ass. She was probably 5’6″ at most. She wore a black tank top and tight jeans with tall black boots. Normal clothes to bystanders, very sexy outfit to me!

When she came inside, she gave me a big smile and I stood up to get a hug like she asked. I could tell she made a point to squeeze her tits against me, and her hand slipped down to give my cock a little grab. I was rock hard in her hand instantly. She giggled and sat down so we could chat. We discussed what I was looking for, services she offers, schedule availability, and prices. She was very fun, and very professional. We determined that our schedules fit perfectly to allow me to stop in on my drive to work, spend about 30 mins there (more if needed), and get back on the road. She even said I’ll be allowed to use the shower if I need to. She is 43 years old, with kids, but single Mom. Her kids are at school when our appointments are planned. We sorted out the details, and i walked her to her car. Before she left, she gave me one more hug and an even harder grab on my cock. While holding me firmly, she whispered in my ear, “save your cum for me hun. It’s only four days away, and I want every drop.”. Then we got in our separate cars and left.

The next four days were tough. I had an almost constant erection, but I made sure to not jerk off. When the day came I wore my best boxers and headed off to work, planning my pit stop on the way. Her house is only a couple miles out of my way. I pulled in and parked in the garage as requested. Nice privacy. She was there waiting with the door open, and wearing a very revealing teddy. I came in and she led me to her living room couch, motioning for me to have a seat. She has a cup of coffee waiting for me and the news on mute. Blinds drawn. I sipped my coffee nervously as she grabbed some towels from the closet.

“Take your clothes all off please, I don’t want you getting your work clothes messy.”

“Yes ma’am” I said with a smile.

I stripped down completely and sat back down on a big towel she put on the couch. My cock was already at full attention, standing straight up. I’m in decent shape, a little beer gut, but not bad. My cock is 7.25″ long and very thick. She took her place kneeling on the floor between my legs. A big bottle of coconut oil was on the coffee table. Grabbing a small glob of it, she rubbed it all over her hands. Then she stared with my balls, surprisingly. She oiled up my balls really gently, occasionally running her nails across them to make me squirm. This teasing was driving me crazy, it felt so good. I layed my head back and relaxed. She began massaging my perineum too. This felt so good as my prostate was swollen from abstaining from cumming for a while. My cock was dripping clear precum onto my stomache. This massaging continued for almost ten minutes, really getting me worked up. She had milked out a nice puddle of precum on my chest.

Next, she took another glob of coconut oil and rubbed it onto my asshole. I love ass play, so I was in heaven. Even more so when she slowly slipped a finger into my ass. This felt incredible, and I couldn’t help letting out a long moan of pleasure. She has obvious experience with prostate milking. Her finger stretched in deep and found my prostate instantly. My cock was bouncing all over the place, still untouched. Her finger began moving inside me and gently massaging my prostate. My cock was leaking out so much clear precum. She continued this for another ten minutes or so before slowly pulling her finger out. She reached into a drawer and took out an Aneros ass toy. I love these toys!! It went in very easy and she pushed my legs together to keep it in. Then she stood up, took out her huge tits, and pushed them into my face. One of her hands reached behind her to find my cock. She finally rubbed some oil onto my cock, but only around the tip. She just barely rubbed my frenulum with two fingers while I got to suck on her beautiful tits. My asshole began spasming and clenching the toy in my ass. This causes the toy to move in and out a bit on its own which feels amazing.

My cock began spurting out ropes and ropes of cum. My whole body shook from the intense orgasm. Most of the cum shot onto her back and ass. I sucked her tits super hard while I climaxed.

She got up, told me to relax with my coffee while she cleans me up. I sipped my coffee and she used a warm washcloth to wipe me off and even gently removed the Aneros from my ass.

I got dressed, paid her with a big tip, and said I’m looking forward to our next session. That was last week. I’m looking forward to my next appointment!!

Source: reddit.com/r/gonewildstories/comments/5dpetj/my_first_craigslist_experience