(M/F) I hit the Craigslist lottery: Andrea, Part I | 2016

Throwaway account. This is 100% true. It’s a long build up, and some may not like the payoff, but it’s what happened. Hopefully there will be more to tell in the not-too-distant future.

It was something I had fantasized about for years. I would read all the Casual Encounter ads on Craigslist. When I traveled on business, I would check out all the ads in other cities. I responded to a few, and posted a few ads of my own, but nothing ever developed.

Then things did start to develop. While on a trip, I posted an ad and I got a response. Thinking it was spam, I replied with little hope of an intelligent reply, but within a couple of minutes she texted back, with a phone number. Unfortunately, the logistics didn’t work out but I was exhilarated.

A few weeks later, I was traveling back to the same city, and posted a new ad. This one was lengthy, detailed, and laid out specifically what I was looking for. And I got a response within an hour. But this one didn’t pan out either - she inadvertently used an email address that revealed her real name, and when I addressed her with it, she sort of freaked out.

But at about the time she declined, I got a really brief email from Andrea:

“Hi there I'm interested... have you found anyone yet?”

“I've got one nibble. Well, two now. Sound interesting?”

“I'm very interested! I'd love to be your little secret here in town! “

We exchanged a few more emails, a few g-rated photos (hers didn’t show her face), and made tentative plans to meet up when I was coming to town the next week.

Some background - I am a married man. Married over 20 years to a wonderful woman. At one time our sex life was terrific, but she now had health problems that had wreaked havoc on her sex drive. I was frustrated, but I managed. I fantasized about having an affair, but up until Andrea, it had remained a fantasy.

Fast forward a few days, and we had made arrangements to meet. She wanted to talk on the phone first, so she texted me asking if she could call. I replied “Sure”.

The phone rang and my heart rate went up 200%. I answered and was surprised at her voice - it was extremely pleasant, appealing, and sexy. And she sounded younger than what she had told me in email. Andrea was definitely uninhibited, but at the same time she was a little hesitant. She expressed some anxiety that I would be put off by her weight - she said “I’m not a Barbie doll”... But I had seen the photo and I thought she looked very sexy. I reassured her that I was not exactly a Greek god myself. She said she was determined to lose weight this year, and her role model was Raquel Welch, since a lot of people had told her they resembled each other. That sounded REAL good to me. She gave me directions on a meeting place in a public area, and we said we’d meet at 7:00.

Now I was really getting anxious. I had never, ever done anything like this before. I had conflicting emotions racing around my brain at 6,000 rpm. I was thrilled, horny, scared.. the whole gamut. Yes, guilt was there too.

By the time I pulled into the parking lot (10 minutes early), I had just about convinced myself that I could not go through with this, and I would explain it to Andrea, and if she wanted to we could just have a nice dinner and call it a night. I sat there agonizing, and Andrea texted me to say she was running late, but would be there around 7:15. I almost bolted at that point, but I remembered how great her voice sounded on the phone, so I stayed.

A car pulled into the adjacent parking lot, and within a few seconds she texted me that she had arrived. I texted back that I’d see her at the gazebo. I took a deep breath, got out and walked to meet her.

My first impression was that she was taller than I expected, and her hair was much longer. We hugged and she smelled fantastic. She was curvy, but very sexy. She also talked a lot. I decided we’d have dinner and I could still bail out if I felt like it.

We ate on a patio, and the weather was really too cold for outdoor dining. I shivered most of the night, partly due to the cold, and partly due to my nerves. The restaurant only served wine, so I couldn’t have the courage-building elixir of bourbon that I had planned. Andrea was mesmerizing. She was completely uninhibited, and talked comfortable about all sorts of sexual topics, including some that were fairly taboo, and had me glancing around the patio to see if anyone had overheard.

She moved her chair closer to mine. The conversation got more personal, and she commented on my big hands, and big feet.. and asked if that meant anything. I replied that I had never had any complaints. She gazed at my crotch, then looked me straight in the eyes. “Oh, I’m sooo going to rape your ass!”

Okay, well, my decision was made. I was going to fuck this girl. Tonight. Assuming my nerves would allow an erection at all.

I almost tackled the waitress to pay our tab, and we headed for her place. I had suggested my hotel room (neutral ground), but she said she lived nearby. We got inside her apartment, and she went into full seduction mode. She lit candles, put on sexy music, sat me on her couch, had me take off my boots, and poured me more wine.

We continued conversation for a while. She quizzed me about my fantasies, asked me if I preferred pussies to be shaved, and at one point she ran to her bedroom to retrieve her favorite vibrator that she felt like she just had to show me. Eventually we started kissing, but before things heated up too much, she pushed the coffee table aside, and positioned herself on the ground between my legs. She started rubbing the crotch of my jeans.. She showed me some lube that was “the greatest thing in the world”. She started unbuckling my belt, and she gasped as she reached into my shorts and pulled my cock out.

I had truly reached the point of no return now. I was still nervous as hell - it was like I was on my first prom date or something. She took my cock in her hands and started stroking it, all the while telling me how gorgeous it was… or something like that. I was in a stupor at this point. We quickly took my jeans off, and she said she was going to get comfortable. She scampered back to her bedroom, and soon came back wearing nothing but panties and a sort of sweater vest. She apologized, and saying that this was the heaviest she had ever been and she was going to lose weight, but I was slack jawed, staring at her boobs.

For the first time, I was able to fully comprehend the majesty of her tits. They were incredible… at least 38DD, and just unbelievably firm. I was truly awestruck...I reassured her that I thought she was incredibly sexy and her body looked absolutely smoking hot.

Soon she was giving me a blowjob that was the best I had ever experienced… slow, sensual, lots of hand action, and every few strokes she would look me in the eyes and tell me about the sexual adventures we were going to have. She serious about sucking my cock and said more than once that she wanted me to cum in her mouth. How I managed not to shoot off when she said that, I will never know.

She slowed down, and I asked her if she was wet.

“You want to see?”

“Oh, yessss”

She then moved to mount me, with those fabulous tits right before my face. She was very, very tight… She groaned as she lowered her hot wet pussy down on my cock. Very quickly she was riding me and grinding and I was mauling her tits. We went at it like that for a good while, then finally we moved to her bedroom.

I wanted to eat her out, and she obliged, but she wasn’t fully comfortable with it at first. Her pussy was succulent.. she tasted sooo great and I licked her as passionately and tenderly as I could.

We fucked some more, and she was incredible. Unfortunately, I was never able to cum… partly because of nerves, partly because of the wine, I guess. Okay, mostly because of nerves, but she was awesome about it. We talked for a long while, and eventually I told her that I needed to leave so she could get some sleep (she still had to work the next morning).

I’m working to schedule my next “business” trip in a few weeks.

I cannot wait.