As you might have guessed from my username, I came of age during the era of AOL. By the time Tinder (or even Craig’s List) came around, I was in a committed relationship with the woman who would eventually become my wife. So in 2000, when this experience took place, the online answer for quick sex or sex play was America Online.
I became pretty good at chatting. I was always pretty good at writing and I was willing to put in the time online to hopefully meet a woman in my area in person. Here and there, you might meet a conventionally ‘hot’ woman, but in my experience, you had to be a little flexible in terms of what the female would look like in person. And certainly I met some thin women off of AOL, but, again, in my experience, most of the women who met me from that forum were on the heavier side. I went to school in Wisconsin, and there were women of all shapes and sizes on campus. So in college I had plenty of hook-ups with women who were larger than me. And I can not say that their weight or body type at all interfered or dampened the experience. In fact, I was so skinny in college and I hooked up with so many curvy gals, that the less genteel of my friends called me a “chubby chaser.”
I lay all this groundwork to introduce J.C. to y’all. I met J.C. on AOL one night and we hit it off. I always found that a good segue on AOL was to ask the woman if she ever met any guys off of AOL in person. I did this with J.C. She had, and, yes, she’d hooked up with several of them. I then asked how far she generally goes with a guy the first time she meets him off of AOL. To this she says that she’s not opposed to having sex if it feels right. She asked me basically the same questions, and I tell her truthfully that it hasn’t happened yet that I had intercourse with any women off of AOL, but when I have been fortunate enough to hook up, I’ve usually 69’ed. I also told her that women have liked the taste of my cum which wasn’t necessarily true. I just never had any complaints! She remarked that this all sounded like fun and that it’s been a while since a guy’s gone down on her. I asked her if she was full, trimmed, or completely shaved ‘down there.’ She told me she was full, but that the hair was very light.
At this point I asked to trade jpegs. She took a while to reply and said, “Okay, but I gotta warn you, I’m pretty fat.” I told her I’d been with some fairly large woman and chances are she’s not “fat.” We traded pics. J.C. had red hair and, indeed, was a fat girl. She said, “You’re cute! Very thin, but cute” To put her at ease, and because notwithstanding her build I still wanted to hook up with her, I said, “Thank you, but I’m large in the right place! And I’m looking at your picture and you are not fat.” J.C. replied, “Aww that’s very nice of you, but I’m over 200 lbs.”
Doubling down on my lie, I said, “Well, I must have been with girls over 250 lbs. because I’ve been with bigger women than you. ”
And you 69’ed with these women?” she responded.
“Not all of them, but some of them, and they seemed to enjoy it. And if your pubic hair is the same shade as the red hair on your head, I’m going to enjoy going down on you.”
“Well, it is. Can you come over tonight?”
I drove 45 minutes to her apartment. Usually, I’d meet at a public place (like Denny’s), and if we hit it off, we’d go back to one of our places. But J.C. moved fast, and I was game. I had butterflies in my stomach in anticipation. Here I was, 23 years old, 5’8”, 120 pounds soaking wet, and I was going to hook up with an over 200 pound woman.
When I arrived she looked very much like her photo with the added surprise that she had a dead tooth on the top row. I thought, “Okay, so you won’t kiss her that much.” She was wearing a shapeless gray, jersey cotton dress. Because I did not see a computer in the main room, I said, “I want a tour. I want to see where you were having this intense conversation with me.” She said (knowingly), “That would be the bedroom.” J.C. led me in. I saw her computer on her simple computer desk and said, “Yepp, there it is.” I then put my arms around her (or at least as far around her as they would go) and kissed her. She kissed back, and I guided us to her bed. Because I did not want to kiss her all that much I said, “I hope I’m not moving too fast, but I really want to see that pussy of yours with all that strawberry blond hair.” “Not at all. I want to see your cock.” I was already fully erect, so I was ready for the big unveil.
We undressed. J.C. had large and, no surprise, saggy breasts. Still she had attractive light pink silver dollar aureolas that I knew would be fun to suck. For a while I did just that, licking and sucking her huge mammaries. I asked if I could remove her panties because I always love doing that. She said, “Sure.” J.C. spread her ample thighs and stuck her feet in the air. I took off her panties to reveal an absolutely beautiful vagina. Dense pubic hair that was even lighter than her head hair and gorgeous bright pink labia. When I spread her lips apart she gaped open to the size of a golf ball! It looked like a very well-used pussy.
“Oh my G-d!” I exclaimed, “I was hoping it would look like this!”
“Thank you,” J.C. giggled, “and I was hoping this [stroking my erection] would look like this, but I think you’d hurt.”
“Well, I certainly don’t want to hurt you,” I said smiling, “why don’t we just 69?”
I then got into a version of 69 position I’d never tried before, but based upon J.C.’s size I thought it best for me to be on top! I straddled my knees along each side of her head and angled my dick into her mouth. I spread her labia with my fingers and started licking her clit and hood. J.C. started moaning immediately. Her pussy at this point was fragrant, but not smelly. Just that sweet smell of a pussy that’s itching to orgasm. Meanwhile, she’s giving excellent head, which if I’m being honest, I had come to expect from fat girls. J.C. was no exception. No hands, very measured bobs. No gagging. Lot of nice tonguing of my glans. It got so good that I actually had to say, “Ohhhh, J.C., this feels so good, but could you take a little break. I don’t want to cum too soon.” So now if she has her eyes open (which I hope she does not) she has a great view of my hairy balls and asshole as I traced the great circumference of her vaginal opening with my tongue. Because she had said it had been a long time since a guy had done this (although I could not believe that because it was such a beautiful vagina), I wanted to really get in there and make her cum. To that end, I remember lifting up her clitoral hood and isolating her clitorus. I then flicked her clit with my tongue mercilessly. J.C. was wheezing from this, and I started getting concerned she might be having heart palpitations. I asked her if she was alright. She said, “Yes, keep doing that.” So I did and J.C. had an orgasm from my cunnilingus.
Feeling a little like Superman, I thought, ‘I can eat her out with her on top.’ So I said, “Now you get on top.” Bashful, J.C., said, “Wait a minute. Are you sure? I’m huge; I don’t want to suffocate you.”
“Yeah, I’m sure. Like I told you, I’ve had much bigger women sit on my face. Come on, I want to make you cum again.”
J.C. complied and now I had a clear view of her rear end. It was quite an ass! Big wide cheeks with cellulite on the base and on her upper thighs. But maybe I really was a chubby chaser because I just saw it as a sumptuous treat. I kissed both cheeks of her ass, spread them apart to reveal her anus for the first time. It was the same beautiful, pink color as her labia minora. No foul odor emanated from it. Just the sweet smell of, well, ass. Her upside down pussy gaped open for me. Delegate fingers from both hands went on an exploratory mission of her inner folds. I ate her out again. Same wheezy breathing. And again, she orgasmed.
Mindful of my request not to blow me lest I cum too soon, J.C. had refrained from doing anything to me up to this point. Now I really wanted to cum. I turned J.C. over onto her back and knee-walked over to the side of her face. J.C. knew what was up and opened her mouth for my penis to enter. She bobbed back and forth as I fondled her breasts. Soon I experienced that familiar feeling. Yepp, J.C. was going to get the sperm. But I was concerned for her safety. I knew she would be the kind of girl who would swallow, but I had been building and building a load since we were chatting online. I knew this was going to be a massive ejaculation, and I did not want her to choke accepting it in that position. So as soon as I started orgasming I removed my penis from her mouth. So there I am kneeling over her tits with her looking up at my cum face. The problem was, in my diligence, I pulled out maybe a second too early. I didn’t start jerking my penis. I wanted J.C. to take ownership of bringing me to orgasm, but I was really counting on the inertia to carry me to the peak of my orgasm so the cum would start flowing.
Right before I reached the peak of my orgasm, a tiny spurt of cum or pre-cum emerged. Obviously thinking this was just pre-cum, J.C. said, “Would you like to put it back in my mouth?”
“No, I’m actually cumming,” I reply. And I barely get the sentence out, and BAM, my cock spasms up and down hands-free and out flies a huge rope of semen landing on her more distant breast. My cock heaves again, this time smacking her nearer breast with cum. I then finished in her mouth. J.C. remarked, “Hmmm, that does taste pretty good,” and started gathering gobbs of my semen off her breasts and sucking it off her fingers.
I never saw J.C. again, but that memory is still fresh in my mind. To this day, it’s still part of my ‘spank bank.’
Source: reddit.com/r/gonewildstories/comments/11jvjf7/my_ons_with_f_i_met_off_of_aol_hours_earlier
This is so similar to my late 90s-early 2000s AOL experiences that I could have written it myself. I eventually married one of those AOL girls.
I started using the AOL chat rooms in the mid 90s and had a lot of experiences similar to this one. Not all were big girls. The average were on the slightly chubby side but so I am so that’s fair. I did manage to hook up with a few that were WAY out of my league but I also leaned that even gorgeous women with amazing bodies have low self esteem and any kind of make attention makes them wet
TIL AOL stands for America Online. I have vague snippets of remembering it but never knew what it stood for.
Great, well written story too of course