[M]y first time with a SSBBW [MF] (long)

Back when Craigslist hookups were still a thing, I used to enjoy a semi-daily peruse through the casual w4m ads. The odd time I’d reply to the ad…and silence. I didn’t think too much of it. I was average looking, and truth be told, a geek.

One day in April, after a break-up I worked up enough courage to post my own ad. I was in search of a curvy/voluptuous/BBW/SSBBW woman, for the upcoming weekend. I’m about 5’10”, brown skin and posted a picture of me smiling in a suit. The next morning I woke up…and over 50 replies! In aroused anticipation I started to go through them all. I quickly noticed a theme…all these ladies were super interested in me, but they needed me to sign up on some website, before being able to talk to me. After going through all the replies, there was one real one.

Her name was Heather…a 48 year old, 5’4″ 390 pound SSBBW, married, with kids. She mentioned that she was very interested in meeting up, but was unavailable to meet that weekend. It was multiple fantasies for me – mom, married and large. Once the blood managed to return back to my brain and fingertips, I responded with a “No worries, I’d be happy to meet in the future.”

After many, many, many conversations back and forth…descriptions/picture exchanges, dirty explicit e-mails, exchanges of fantasies (public sex was a particular turn on of ours, as well as bareback/creampie), I was dying to have her in person. She was a little bit unsure if I would be attracted to her in person, but I sent her some pictures of the effects she was having on me and it seemed to placate her. It was August by then, almost 4 months of lusting after one another. We planned to meet up the next morning, at a public park, with Heather telling her family she was going on a long shopping trip.

We were to meet at the park at about midday. I went a bit early, just to scope an empty place out. It was so hot I was already sweating just driving. The park didn’t have any private areas…but there was a nice shaded bit in the parking lot, which I parked my tinted minivan in. She pulled into the parking lot in her truck and my heart started to race a bit.

She came out of the drivers side, and before we even exchanged any words, we started to make out, leaning against her truck, my hands caressing her ample behind. We stopped to catch our breath a few minutes later…she grabbed my erection and said with a smirk “seems like you’re still interested.” She came close to my ear and asked me if I found any spots…I said there were too many people in the park to find a good spot.

She motioned to get in her truck and we opened both driver/passenger doors out, giving us some privacy. About 5 seconds after that, my shorts flew off and she went down on me. Now, I haven’t had a lot of blowjobs (I’m in single digits) but this was an incredible one. The amount of suction, spit and sloppy noises and I was about ready to erupt less than a minute in. She eased off and gave me a chance to recover my dignity. I suggested we move to the back of my van.

I had prepared my van by removing all the seats, opening a lot of space. She eased herself onto the floor, while I closed the trunk of the van. I stripped down to my birthday suit as fast as I could. She was wearing shorts and a dress that took only marginally longer to take off. I laid on top of her, and we began making out again. She had a certain skill with her tongue that I rather enjoyed. I started to leak too much precum onto her belly, so I got off her. I was ready to fuck, but thought I should do the gentlemanly thing and reciprocate.

I went down and began to lick and suck her extremely wet pussy. I’m not the most skilled…but something I was doing was working for her. After a few minutes, she wanted me inside her. I got up onto her belly again, staring deep into her eyes, and thrust my bare cock inside of her, to the hilt. She wasn’t the tightest (who would be after having two kids) but she was so incredibly wet and warm, the taboo of having sex with a married mom, in a public park…I can truthfully say it was the most aroused I’ve ever been during sex. 

I didn’t want to lean to much on her belly, so I propped myself up a tad, almost like a pushup. Not only did it give me a great angle and thrusting power (her stomach and breasts were jiggling in all different directions), it was a bit painful on my arms…which distracted me, allowing me to extend the wonderful horizontal mamba time. 

It being a hot day, my sweat was literally dripping onto her, which was turning her on even more. A few times people had ventured close by outside my van, so I stopped, with my cock twitching inside of her…which got both of us excited. As soon as the people had moved a sufficient distances away, we slammed our pelvises together, thunderously. Eventually, after what felt like an hour (but was probably only about a half hour) I told Heather I was going to cum…she wrapped her legs tight around me. I coated her insides with a healthy dose of my semen and promptly collapsed on top of her. 

After a few minutes of catching our breath, we got our clothes back on and opened the trunk of the van (airing out the smell of sex) to cool off. After about 5 minutes she asked if I was ready for round two…but with the heat and the sweat, I didn’t think I could get it up again. We made out for a few more minutes and then she left for home.

We stayed in touch for awhile, but could never make another meetup work (work, kids, period, etc.). I still think fondly back to that day.

Source: reddit.com/r/gonewildstories/comments/bcan56/my_first_time_with_a_ssbbw_mf_long