u/AOLGeneration

The amazing thing about America Online ("AOL") was that if you worked it just a little, you could daisy-chain multiple hook-ups off of it. The culture of AOL lent itself to ask someone new that you'd meet if they had ever met someone else off AOL in person. Invariably, you both had and then it was a sentence of two before you're telling what you did with your past partners. I'm here to tell you - there was no judgment. No one ever thought of the other as a 'slut' or a 'man whore.' Rather, you held each other in esteem; it was erotic to hear what they did in the past and what they, hopefully, will do with you if/when you met.

This phenomenon was best illustrated to me in 1998-99. In the summer of '98, I had a FWB relationship with a girl two years younger than me named Julie. Julie lived in a nearby suburb but attended a different college. A brief description of Julie's charms: She was Italian with a pretty face; large conical breasts; a trimmed yet ample brown bush, a musky - dare I say, stinky, pussy with a shell-like, wide vaginal opening. We hooked up twice in the summer of '98. Each time, I went down on Julie, and she returned the favor with a blow job. Cumming with Julie was interestingly consistent but by no means boring: Each time, after a delightful orgasm with my penis firmly planted in her mouth, the first heave of semen literally sailed down Julie's throat and was met by a guttural swallow on her part. She gamely swallowed all but the last two spurts of cum, which landed in my pubic hair.

When Julie and I were at our respective schools we communicated a lot by this new thing called 'AOL.' At some point in late '98, Julie starts going out exclusively with a guy she met at her school. No big deal; I was happy for her. We were always FWB's, both of us not wanting to do the long distance thing knowing that we'd have plenty of options on our respective college campuses. (Her more so than me!) But we would chat, platonically, when we happened to be on AOL at the same time.

By 1999, beyond using AOL as a means to keep in touch with friends, I had hooked up with a fair amount of women chatting with members in my geographical area. I recounted this to Julie in one of our chats in the fall of 1999.

I tried to be as innocuous as possible and said, "You know, this AOL is actually a pretty good dating tool."

There is a longer delay in Julie's response time than I typically experienced, and I'm beginning to think my attempt at being innocuous wasn't so innocuous.

But eventually she replies, "I know! I have a friend, Natalie, who's met a few guys off of AOL. If you want, I can ask her if she'd like me to give you her screen name so the next time you guys are online at the same time, you could chat."

I tell Julie that I'd love to get Natalie's screen name. Julie asks her, and Natalie was fine with it. I'm pretty sure Natalie and I were both on AOL the very evening Julie gave me her screen name, and we hit it off.

In our second chat I asked Natalie if she ever met any guys off of AOL in person. Correctly sensing that I already knew the answer through Julie, Natalie coyly responded, "I think you already know I have ... "

Upping the ante, I replied, "Alright, alright, Julie did tell me you met some guys in person, but she didn't tell me how far you went with them when you met."

Natalie said, "I should hope not," in mock indignation because shortly thereafter a new message popped up: "Kissing, feeling up and if I'm feeling particularly frisky I might allow some fingering and give him a hand job."

Natalie, in turn, asked me the same question, and I replied that I don't usually have sex on the first meet-up but I'd likely do everything up to that point.

Natalie replied with the then-nascent term "lol," and went on to type, "I'm glad you're being honest."

"What do you mean," I queried (pretending not to know).

Natalie replied that a "little birdie" told her that I like to "go down," and that I was "very thorough."

I thanked Julie in my head for the endorsement, and in response to Natalie I thought it couldn't hurt to give Julie an endorsement of my own, typing, "Ohh, I think I know who this 'little birdie' is and, while not going into details, I will say I really enjoyed going down on her."

Generously, Natalie intimated, "Lol! Yeah, she enjoyed it too."

So now Natalie is intrigued. She knows I went down on her friend, that her friend liked it, and that I enjoyed doing it. Chances are she'd like to have her pussy licked too and tell Julie all about it. I don't mention any of this thought process to Natalie. Instead, with her Thanksgiving Break arriving soon, I tell her that I'd really like to meet her in person over her break from school. She wants to meet me too, but she asks if I can bring a friend and she can bring a friend and make it a double-date.

I agree that it's a great idea, and I had just the wingman in mind, my buddy Brad. So now Brad is likely going to get to hook up, and he hasn't invested one minute of chatting on AOL. But that's part of the magic of AOL, isn't it? My house is vacant for a few days over Natalie and her friend's break. During this time I arrange to have Natalie, her friend (not Julie), and Brad over. After watching a movie, Brad and Natalie's friend go to the guest room and hook up, and I give Natalie 'the tour' of my house. The tour naturally ends in my bedroom. As soon as I shut the door, Natalie and I are kissing. Natalie has a very pretty face with sandy blond hair and a voluptuous figure. I would say Julie had a slightly better body than Natalie, but Natalie's face was prettier. Natalie does not want to take her bra off, but she does let me remove her pants. She's hesitant to let me finger her because she's on her period. I can tell Natalie has a tampon in, so I say what I have in past situations, "We can leave your tampon in, and I can lick your clitorus," (a concept I privately think of as 'eating around the string.') Natalie responds with that erotic mix of embarrassment trumped by horniness, "Uggghhh, I can't believe I'm letting you do this, but, okay, let's leave my underwear on, but if you want to slide them over you can go down on me."

I wasn't sure why she wanted to leave her panties on because when I slid them aside, I really slid them aside, exposing her entire vulva. But I wasn't going to object if keeping them on made her feel more comfortable. She had very close to a shaved pussy, just some very closely shorn dishwater blond hairs above her clit. She has bulbous labia majora, but, using both hands, I spread her outer labia apart to reveal the cutest, tiniest, pink pussy nestled within. Yepp, there's that tell-tale string dangling from her inner folds. I proceed to lick and kiss her clit; it's decidely small but stiffened in arousal. I continue doing this for I'd say 10-12 minutes, and Natalie has an orgasm. Rather than her stated hand job, Natalie returns the favor with a deep throat blow job. My lamp is on so I'm watching this amazing feat. I even said, "Wow, Natalie, deep throat!" She laughed through her nose (my cock fully inhabiting her mouth and throat) and smiles up at me with her pretty eyes. It was a total queen move! She doesn't have to work too hard; about two minutes into it I moan, "Uggggghhhhh, here it comes ..." I thought that, like Julie, Natalie would attempt to swallow my load, but as soon as I announced, Natalie took me out of her mouth and jerked out four 'silly strings' of jism on my abdomen and chest.

Natalie got me toilet paper from my bathroom so I could clean up and said, "Sorry, Julie warned me about that; I didn't think I could swallow all of it."

I responded, "Don't worry, I have absolutely no problem with it, and, yes, both you and Julie made me cum a lot!"

I then I told her that her vagina would look beautiful with her natural blonde hair and that she should grow it out.

Natalie laughed and said, "You know what? I'm going to take you up on that; shaving is so uncomfortable for me."

Natalie goes back to college after Thanksgiving break. December rolls around, and I'm on AOL. I met a woman named Angie. We hit it off. Yes, she has met guys off of AOL in the past. I didn't ask what she did with them, but she asked me when I last met a girl off of AOL and what I did with her. I referred to my tryst with Natalie less than a week earlier and told her that "I went down on her, and she blew me."

Angie responded faux-shocked with, "Woah! On first meeting?"

Now, as I said, Angie was faux-shocked. Even though I was taking a more reserved, gentlemanly approach to my AOL strategy tonight, I knew she had met at least one other guy before me and hooked up if not fucked him. So I said something that always seemed to work when I'd get the faux-shock treatment about Natalie (which also happened to be true):

"Well, we were both attracted to each other, and it just felt right."

Expectedly, Angie was satisfied with my response, and she met me at a local diner that night. Angie and I hooked up, but for purposes of this story, I'll report that I ate Angie out and she gave me a hand job while I did so. (In case there's any interest in reading the complete gonewildstory of Angie and me, here it is:

 https://www.reddit.com/r/gonewildstories/comments/1on54z3/ready_aim_fire/

Meanwhile, I'm still keeping in touch with Natalie over AOL when we both happen to be online. Shortly after my hook-up with Angie, Natalie and I are chatting. I asked if she was still growing out her bush. She said, "yes." I then ask if she's been hooking up at school. She tells me she gave a guy a hand job under a blanket while watching a movie at a friend's apartment. Perhaps concerned that such an admission might spoil a future rendez-vous, she adds for good measure, "Don't worry, he didn't have as big of a cock as you."

I say, "Lol. Thanks for that! And I'll bet that hair didn't stand in the way of this guy fingering you."

Another "lol," from Natalie and "Nope. I wish it did. He tried to put too many fingers in at once."

"Oh no," I typed, "You have a very cute but tight vagina. Even if you weren't on your period when we hooked up I still would have only put one finger inside of you."

"Aww, such a gentleman," she replied, "How about you? Any hook-ups?"

I tell her I met a girl off of AOL earlier that month and went down on her. She replies, "Mmmm, lucky girl. Did she return the favor?"

"Kind of," I reply, "She did the same thing to me that you did to your guy under the blanket while I ate her out."

"Awww, that's no fair" she sympathized, "If a guy's going down on me, I'm going down on him."

"Oh yes, I remember! Trust me, this girl had nothing on you, Natalie."

I then add, "Hey, with Winter Break around the corner, would you like to get together again when you're in town?"

"I'd love to," Natalie sweetly replies.

Winter Break arrives, and Natalie and I see a really slow movie, The Straight Story. I'm playing with her newly grown-in bush the whole time. No fingering because, alas, it's that time of the month again for Natalie. Natalie is fondling my penis inside my pants. Eventually I had to move her hand and whispered, "This feels so good, but I don't want to cum too soon." I tell her this which elicits a grin and eyebrow raise. We hold off until we can get back to my once again vacant home. Once again, Natalie does not remove her bra. She does let me take her panties off. There's that familiar string but this time there are ample dishwater blond hairs above the clitorus and down the sides. Not too long because she's only been growing it out for a month or so, but beautiful. I lick her clit again. Afterwards she gives me the same awesome deep throating blowjob. I announce, "I'm gonna shoot." Natalie giggles, again, removes my penis from her mouth, jerks me off and this time I outdo even last time's watershow. "Yepp," I could never swallow all of that," Natalie says.

My senior year of college I worked as a student fundraiser at a phone bank where we solicited donations to our school from alums and parents of current students. On break, I overheard a 19 year old sophomore girl mention to another coworker that she had to take the bus back to her apartment. I had noticed this girl before. She had a striking face with auburn hair, but the most eye-catching aspect about her was her ass. She had narrow shoulders, probably B-cup, perky looking breasts, thin-to-athletic legs, but a nice, round ass that stuck out nicely whenever she wore pants. I had wanted her sexually since the first time I laid eyes on her, and now I saw my opportunity.

I had a car that year, so later on I went up to her and offered to give her a ride back to her place instead of her having to take the bus. She seemed so appreciative of my offer and relieved not to have to take the bus that I asked her out to dinner before taking her home. She was totally game; I took her to a casual yet quality French bistro near the phone bank where we worked. It was a good call because in getting to know each other I learned of our shared appreciation of foreign cinema, especially French films. She seemed interested in me romantically, but she was formal and seemingly inexperienced. For my three previous years in this college, I typically met experienced gals. Everything they were doing with me, they had done before with plenty of other guys and would do again next weekend with plenty more. In other words, sluts. This girl seemed different. Still, I figured I'd roll the dice and ask her back to my apartment where I had the French classic, The Discreet Charm of the Bourgeoise (1972), rented. Sure enough, she was interested in coming back to my place after dinner to watch it.

We watch the film, and then I make a move on her. It is well-received, and we go to my bedroom. Our shirts come off and pretty soon and I'm sucking her bare breasts. They do look like B-cups bare and have nice pink nipples and aureolas. I start rubbing between her legs; she spreads them and moans a little. Not soon thereafter I take her pants off and see that her panties are already moist. I can tell even with her underwear on that she had a delicious, curvy ass. I had really wanted to get this sophomore naked this first night together, and those moist panties made me think she might be game. Plus, I desperately wanted to see that bubble butt of hers. I took a shot and started to remove her underwear. She actually assists, so now I start taking off my own pants and underwear. Recollecting her formal reserve at dinner, I'm wondering if I'm going to hear an "Ummmm, what are you doing?" But she doesn't react that way and appears to consider my disrobing perfectly normal.

So now we're both completely naked and though I usually would finger a woman's vagina beforehand, I make a dive straight for her pussy. Her legs spread reflexively, and I'm eating what turns out to be a fragrant, vagina with pretty pink lips with a nice triangle of red/auburn bush above it. Even though I'm in heaven licking this sophomore's hairy, musky pussy, I'm also intermittently flipping her legs back in order to kiss those sumptuous ass cheeks. She has no problem with this and is moaning from the ass-kissing the same as she was from the pussy-licking. I return to her pussy, and I use my thumbs to separate her clitoral hood from her clitorus. I then start flicking her clitorus rapidly.

She moans and uttered a really funny line: "Yeah, lick my baby clitty." I got a kick out of that because, while she had a somewhat small clitorus, I would never think of it as a "baby clitty." I mean I'd seen plenty of bigger clits, but I'd also seen smaller ones up to this point. Still, who was I to correct her impression of her sacred rosebud? I continued to flick her "baby clitty" with my tongue, and the next phrase out of her mouth was, "Ohhhh, I'm having an orgasm." Not bad for an impromptu date resulting from a work night.

After she cums, she kneels to the side of me. This would have been the fall of 1998, but I can still recollect smiling in that dopey manner I'm sure every college guy does when he knows what's about to happen next. Yepp, she starts sucking my cock. Her technique was somewhat tentative, licking and sucking on only the tip of my erect penis. But I could empathize with her because I have one of those glans that could look pretty intimidating especially to a woman who is somewhat new to giving head; it's long and thick like a mushroom cap. Still, with all of those nerve endings on my tip alone, had she kept doing what she was doing she would have made me cum nonetheless. However, as she got more acquainted with my penis, she became more confident. She started bobbing up and down on my cock, and while not deep-throating it, she definitely gave it the old 'college try,' taking my penis as deep as she could.

After maybe three minutes of this it was now my turn to reach orgasm. Though it was always my custom to announce before I ejaculate, I felt it particularly appropriate in this situation because - though she gave great head - I still did not think this girl had given many blowjobs in the past. I groaned and said, "Ohhhh, I'm gonna' cum," when I first started orgasming to give her a good 3-4 seconds of lead time to avoid the ejaculation in her mouth. She wasn't taking the cue, however, and kept her mouth firmly locked around my shaft. 'Alright, looks like I'm getting swallowed tonight,' I thought as I savored what turned out to be at least a six second orgasm. When my orgasm finally transitioned into its ejaculatory phase, the first shot of semen was so powerful that it basically sailed down her throat. I heard her gag, she removed my heaving penis from her mouth and my semen flowed down the length of my shaft like lava down the side of an erupting volcano, landing on my hairy balls and bed spread below. It was quite a mess but a mess to be proud of like a 'white badge of courage.'

Thoroughly embarrassed, she said, "Sorry, I'd never done that before. I thought I'd be able to swallow it, but there was just too much."

I reassured her saying, "No, it's totally okay. I only came that much because you gave such a good blow job. I can't believe that was your first time!"

It is possible that she just said that so she wouldn't have to swallow my load, but I still think she was telling the truth. I thoroughly enjoyed the evening as I think she did too.

Recollecting a random hook-up from nearly 25 years ago, it struck me that this woman was remarkably generous with me, a veritable stranger.

It was the summer of 2002 and I was living in downtown Chicago. I had been out at the bars with my buddies, and while we went up to some ladies, nothing materialized that night in terms of any of us hooking up. So when I got back to my apartment, I went on AOL. I wasn't drunk to the point of sleep or illness, but I certainly had a few drinks that night. Lo and behold, when most guys might have called it a night, my night appeared to be just beginning at past 1 in the morning. I had met a nice woman in my general area. She was on AOL for similar reasons - she had been out to some different local bars with friends, had kind of a boring night, and was not ready to go to sleep.

Naturally, I steered the conversation to her AOL experience, asking if she turns to AOL to meet people when the conventional venues (i.e., bars/clubs) prove to be duds. No surprise, she has, and I admit that I have too. Since it was past midnight, I didn't think it would be too bold to ask if she'd ever met any guys off of AOL, and, if so, what she did with them. She said, "Sure, I have. Some it was just coffee, and we never saw each other again. Others, well, let's just say we had a good time."

She directed the same question to me, and I truthfully told her that when I've met women from AOL in person it's usually resulted in a hook-up. I admitted that I hadn't had intercourse with any of them, but I usually gave them oral.

This elicited a ( : emoji, and, as I had hoped, it peaked her interest as she then typed, "So you like going down on girls?"

I wrote back, "Absolutely!"

She replied, "And it isn't weird for you doing that with girls you barely know?"

Fearing I might be losing her I replied, "No, it's so intimate that it works to speed up my getting to know them."

"Good answer," was, to my relief, her reply!

So I made my move. I suggested we meet at an all-night diner pretty much equidistant to our respective places, and if we like what we see, we could go back to one of our apartments. If not, no biggie, it would be just another of those 'coffee only' dates.

She was game, and half an hour later we were sitting at an outdoor table across from each other.

She was Polish and had a very pretty face with strawberry blond hair. She was pale-skinned with a good complexion. She wore cute glasses and dressed in a stylish way. In terms of body type, she was fat, but nothing out of the ordinary for AOL standards. Indeed with her heaving breasts and big, round ass hers was a figure I had come to appreciate - if not relish - and I knew if I were lucky enough to get her back to my apartment (or go to hers) I could have a lot of fun with her curves.

She seemed equally taken with me. We had a delightful time. The weather was so nice that we sat at an outdoor table in front of the actual diner. Not just coffee, but eggs/breakfast food too. That struck me as a good sign because if you want to make a quick get-away, it's easy to finish a cup of coffee and be on your way (as compared to a full meal). When we both finished and I paid the bill, I cut right to the chase and said, "Well, I certainly like what I see, would you like to come back to my apartment?" With a twinkle in her eye, she replied, "Sure."

As if our date wasn't pubic enough, when we got up and before we made our way to our respective cars, I put my arms around her buxom body and open-mouth kissed her in front of the other diners and passers-by. (It was a very popular late-night restaurant especially on the weekends.) She was very receptive, and followed me back to my place.

Once we arrived, I took her to the bedroom where we continued our kissing. Of course, neither one of us wanted to just kiss at 3 or 3:30 in the morning so we started taking off each other's clothes. Five minutes into walking into my apartment, we were both completely naked. Big round titties with pink nipples, a soft belly, and a beautiful pelt of strawberry blond pubic hair. Her legs were fairly big, but I liked them. Wide hips and thighs tapering down to athletic shins and ankles (kind of like a lot of female soccer players I had seen).

I remarked, "I knew I liked what I saw earlier." Then I said, "Especially this," as I stroked her strawberry blond pubic hair.

"Hmmmmm," she quipped, "Does it look good enough to eat?"

"Oh yes," I reply.

"Mmm good," she purred, "I was curious about your skills ever since you told me you've gave oral to other women off of AOL."

I laid her on her back, opened her thick thighs, and took my first delicious lick. She had pretty pink labia minora. Not much of a pussy smell that I can recall, but she was wet with grool, and she moaned enthusiastically as I licked her clitorus and inserted my index and middle fingers into her vaginal opening. On my end, I moaned a little too at the look and taste of her pink pussy and strawberry blond bush and uttered, "Mmmm, beautiful," as I kissed her labia and pubic hair. Her moaning continued and eventually she sighed, "Ohh, you made me cum."

Looking to repay the favor, she got on her knees and started blowing me. I was erect, and her head was good, but I was having a hard time reaching orgasm. After blowing for longer than I think she should have had to, I said, "I'm sorry I'm making this so hard on you. I think it's that I drank a good amount when I was at the bars with my friends earlier."

"That's no problem," this kind stranger replied, "Would you like to have sex instead?"

I knew there would be a first time fucking a woman I met off of AOL, so why not this sweet, buxom redhead, I thought.

"I wasn't lying earlier," I responded, "This would be an 'AOL first' for me, but I'd love to."

I got a Trojan Magnum out of my night table drawer. Now anyone who has read any of my other gonewildstories knows that I had an awful time of it with condoms, even the Magnums. But I figured I'd give it the 'old AOL try.' I managed to put on the condom and stay hard. I stood to the side of my bed and flung her legs wheelbarrow-style over my shoulders. I penetrated her and thrusted back and forth several times. On her end, she seemed be enjoying the fucking from the get-go. She let out a nice moan as soon as I got my penis balls-deep inside of her. Unfortunately, as was often the case, the condom robbed my penis of all sensation, and somewhere after the fourth or fifth plunge I lost my erection.

Unphased, she unrolled the condom from my flaccid penis, discarded it on the floor, and started blowing me again. Very good head, and my erection returned. However, I think that alcohol from earlier was still getting in the way of my cumming. Since she was such a trooper and knowing how much her pussy turned me on, I said, "Would you mind if I went down on you again?"

"Not at all," she replied with a big smile worn by a woman who clearly likes having her pussy eaten. This time she knee-walked over and sat on my face. As she did this I noticed her pink nipples were beautifully stiffened. I quickly stole a pinch one each one with the middle and index fingers of my left and right hands. At this point her pussy had a definite fragrance. Not bad, kind of sweaty as though her vagina was telling me, "Yeah, I came, and I'm gonna' fucking cum again." She expertly hovered her hairy pussy over my lips and tongue so that I had breathing space, gripped the headboard of my bed, and I eagerly performed cunnilingus on her once more. Once again, she announced that she had cum.

She flipped off and kneeled to my side. Having tried her mouth and her pussy on my cock, this magnanimous girl next attempted an old fashioned hand job. Her hand technique was good. In fact, she mirrored the way I happen to masturbate. So it was lamentable that I couldn't give her the cumshot she was so diligently attempting to get out of me. That G-d damned whisky dick of mine!

Still, I was hard, and it was a good hand job. It felt good as though it had the potential of bringing about an orgasm. For encouragement I said, "It's slow tonight, but I feel like you're going to get me there."

"Good," she said with a smile, "Because I really want to make you cum."

It was at this point that I thought, 'Isn't this a lovely person? She really doesn't know me from Adam and yet she genuinely cares about my having an orgasm.'

After another five minutes, she got really creative. "I know what to do," she remarked with a look of certainty.

She had been pumping my cock with her right hand. Before I could ask what she was going to do, she deftly inserted one of her left fingers into my anus. She wiggled it around a little, and I kid you not, no more than five seconds later I had an awesome orgasm. I groaned and said, "Yeah, that's it! Ohhhhhhh, I'm gonna' cum." I started nutting and she both jerked off and kept her finger in my ass until the last drop of semen emerged. Without a trace of sarcasm, she uttered a genuine "Yayyyy," as I provided 'proof' of the orgasm she so diligently worked to elicit. By the time I was through, my abdomen and torso were drenched in thick, white cum.

I thought then, as I think now, 'what a kind stranger.' I mean we knew each other for less than four hours, but like I said over AOL chat, when you go down on a woman early, you get intimate much faster. That was the case for sure with this sweet lady.

When I was in college at the University of Wisconsin in the mid-late '90's, I was single and lucky enough to hook up with some beautiful women with killer bodies. However, at my particular school, there was no shortage of corn-fed, Wisconsin gals with huge breasts and often even bigger asses. It may have been the era or it may have been the extremely cold temperature for most of the school year at the UW, but these women also tended to have full bushes. As I experienced more and more of these Wisconsin beauties, I developed a fetish for gals with huge asses and hairy pussies. I don't know, but for as long as I was single and meeting a whole assortment of women, maybe every two or three months I'd have a real hankering to hook up with a fat chick with a hairy pussy.

By the early 2000's when this story took place, I was in grad. school and still single. Starting in, say, 1998, I began chatting on America Online (AOL), and I quickly learned that it could be an effective way to meet and hook up sexually with women in whichever area I was living at the time. I became pretty good at chatting on AOL (as my username would suggest). I was always pretty good at writing and I was willing to put in the time online to meet a woman in my area in person. The great thing about AOL was you had the freedom to chat about your preferences - indeed fetishes - to find out ahead of time if your potential partner met your specifications. This was perfect for those times I felt that hankering for a fat woman with a hairy pussy.

I lay all this groundwork to detail my experience with a woman I will abbreviate as ‘J.’ I met J 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. 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 (music to any AOL warrior's ears). She asked me basically the same questions, and I tell her that it hasn't happened yet that I had intercourse with any women off of AOL (which was true at the time), 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 it had 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. Alright! I had the hairy pussy half checked!

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." At that I took out my cock and started masturbating in anticipation. I found the very package I was yearning for that night! I certainly wasn't going to tell her that. Instead, I told her - truthfully - that I'd been with some fairly large woman and chances are she's not "fat." We traded pics. J. had red hair and, indeed, was a fat girl. So now I'm stroking myself with reckless abandon. She said, "You're cute! Very thin, but cute" To put her at ease, and because I wanted to cum for her and not alone on my computer screen, 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. 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. 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, and I actually found it refreshing that she owned her looks and body. In the world of cat-fishing, it was nice to see some truth in advertising! 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 replied, "You're just trying to get into my bedroom," but with a knowing smirk, J. led me in forthwith. 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 we both knew why I was there and I was so horny for her pussy I somewhat boldly said, "I hope I'm not moving too fast, but I really want to see your vagina with all of that strawberry blond hair around it"

"Not at all. I want to see that cock you were bragging about an hour ago."

I replied, "Well, you got me so turned on, J., I'm proud to unveil it." With that I took off my shirt, socks, pants, and underwear. I knelt on her bed, my erection impressively displayed like a samurai sword. Even my balls were swelled from all the stroking and delaying I had been doing during our online chat earlier. J. removed her jersey dress and bra, leaving her white, cotton 'grannie panties' on. I was glad she kept her underwear on because I always loved revealing woman's vulva for the first time by peeling off her panties myself.

J. 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 actually said, "I'm happy you left your panties on because I find it really erotic taking them off. May I?" J. replied, "Now why did I get the feeling you'd be the kind of guy who'd be into that.'

With that J. 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. 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, "how 'bout we 69?"

"I think that would be a lovely idea," J. politely agreed.

Based upon J.'s size I thought it best for me to be on top. I then did something I always got a kick out of doing: using language (much like a porn director) to establish the positioning of a sexual act. In addition to the hotness of articulating what we were doing, I had never attempted 69 man-on-top, so this 'oral direction' served the function of getting it right this first time.

To this end, I said, "Okay, let's get you on your back over here."

I then added, " I'm just going to straddle my knees along your head like this," as I got into that position.

"Okay, if you're ready for it, I'm going to put my penis into your mouth."

J. giggled and replied, "Oh yes, I'm ready for it."

I then angled my dick into her mouth and as soon as I felt her tongue lash across my glans I uttered an "Mmmm, that feels nice." I then spread her labia with my fingers and started licking her clit and hood. J. 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. Continuing the trend of open communication we'd been enjoying I echoed my admiration of this by saying, "Ohhhh, your vagina smells and tastes so good."

J., now with a mouth full of cock couldn't exactly formulate a 'thank you,' but she replied graciously with a moan that sounded like an "uh huh."

Meanwhile, she's giving excellent head, which if I'm being honest, I had come to expect from fat girls. J. 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., this feels so good, but could you take a little break. I don't want to cum too soon." J. released her mouth from my penis, and I remember, basically proving my claim, my cock spasmed. Nothing came out, just a subtle twitch to show J. how close I was to cumming. While I wanted J. to see that what I didn't want her to see is this 'great' view of my hairy balls and asshole as I traced the great circumference of her vaginal opening with my tongue. But having always been on the bottom of a 69, I was keenly aware of what J. would be seeing. I decided to put it out of my mind. In doing so, I wondered if all the girls who sat on my face in the past did the same mental thing despite the look of an upside down, hairy vagina being the most beautiful image in the world to men (or at least this man). I couldn't imagine my scrotum was nearly as aesthetically pleasing, but I decided to just focus on giving J. pleasure. 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. 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. 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, 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," I lied, "I really want to make you cum again."

"Well, when you put it that way ..." J. retorted as she flopped over and hovered her ass and pussy strategically over my face.

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 I was a chubby chaser; 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. As I recall, I didn't comment on it, but I intimated my arousal by inhaling through my nose - mere centimeters from her asshole - and softly moaning an "Mmmmmmmm." As I spread her further apart, 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. had refrained from doing anything to me up to this point. Now I really wanted to cum. I turned J. over onto her back and knee-walked over to the side of her face. This time with no verbal communication from me, J. did what came naturally and welcomed my penis into her mouth. She bobbed back and forth as I fondled her breasts. Not surprisingly, that same pleasurable feeling as before took hold in my penis. Yepp, J. 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, as mentioned earlier, I had been building and building a load ever since the edging I was doing during our online chat. 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 that pleasurable feeling crescendoed and I reached that point of no return, 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 because I wanted J. to take complete ownership of bringing me to orgasm. However, I was really counting on 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 semen emerged. Obviously thinking this was just pre-cum, J. kindly offered, "Would you like to put it back in my mouth?"

"No, uggggghhhhh," I moan, my face contorted from the ecstasy I'm experiencing in my penis, "It's okay, you already brought me to orgasm." 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. Still ejaculating, though not as violently as I had just done on her breasts, I directed my penis into her mouth, figuring she might like a taste. J. welcomed my quivering member back into her mouth, allowing me to finish therein. Reflecting on my earlier quip, J. remarked, "Hmmm, I agree with your other women, that does taste pretty good," and started gathering gobbs of my semen off her breasts, sucking it off of her fingers.

From what I learned about J. in our chat, I believe she was just about to travel to Asia on some sort of a teaching/study program at the time of our tryst. It just kind of 'worked' that we were able to share this many-splendored night together before she left the country. So I never saw J. again, but that memory is still fresh in my mind. To this day, it's still part of my 'spank bank.'

In the fall of 2000, I and a couple of mutual friends, visited a buddy in law school. Turned out, I was the friend who 'got lucky,' and I hooked up with one of his classmates, Becky, who came out to the bars with us. Becky was a PAWG (Phat Ass White Girl) with nice, pendulous breasts with big nipples and, though slightly trimmed, a meaty, pinkish-red vagina with ample black pubic hair around it. Our hook-up consisted of my going down on her for a good half hour and her returning the favor with a pretty awesome blowjob. She did not go down on me nearly as long as I went down on her. I think I lasted all of four minutes when she made me cum. She gamely swallowed a sizable load, jerking only the last couple of spurts outside of her mouth. It was a passionate hook-up, but I think we both chalked it up to a one-night-stand. I didn't have any plans to return to my buddy's/her law school, and we lived in different states when school was not in session.

However, Becky visited my hometown the following summer (2001), to visit my buddy and other law school friends who lived here. She came in on a weekend, and stayed at my friend's apartment he was renting. I was not able to hang out with her and our friends on Friday night, but I went downtown the next night Saturday ready to see Becky once more. I took along a Trojan Magnum condom too.

Though we hadn't talked in the 7-8 months since our many-splendored evening in her law school town, we were able to pick right back up where we left off and had a nice time out at the bars. I accompanied her back to my friend's apartment. He had a one bedroom, so he politely went into that bedroom to go to sleep as soon as we got there. We were alone on the living room couch. We both wanted each other again so without any delay, we started kissing and undressing. There were those pendulous breasts again with those big nipples. I recall she had a long jersey cotton or rayon, black skirt on with an elasticized waist band. I took that off and had her in her black panties. I was already naked and erect at this point, so with her chubby legs in the air, I pulled off her underwear. Her vagina was already creamy, and, thankfully, she still had that nice black pubic hair around those meaty red/pink labia.

Her grool was already coating the pubic hair closest to her opening. I actually moaned at the sight and could not resist taking a nice long lick along her labia and moistened pussy hair. Though hard to explain in words, she had that 'good stink' to her vagina. I guess the most scientific way to put it was she was sending me her pheromones. Kind of like, "Damn, this smells, but at the same token I can't take my nose and tongue away."

I thought about her hungry pussy and that gold foil-wrapped condom in my pants pocket and asked Becky if she'd like to have sex. "Yes," she whispers, and gets on all fours with her legs conveniently spread apart. I open the Magnum and manage to get it on without losing my erection. Not often the case with me. So now with my right hand I paint stoke Becky's labia with my penis and insert it into her vagina. I gingerly placed my hands around Becky's waist ready to go to Poundtown on this PAWG. However, I can't feel a thing. From the looks of how her labia minora gripped my erection, it would appear Becky has an awesome love chute, but the condom robbed my penis of all sensation. I managed to give her one pump to which she let out an encouraging grunt. Then I lost my erection and slipped out.

"We could do it without a condom, if you want," Becky gallantly offers.

But I got the impression that I was not the only guy with whom she would have done that ... a wee bit of foreshadowing here. In addition to the disease risk, to give Becky the full credit she deserves, having had my face down there now two times and now having seen the 'perfect fit' our genitals created, it definitely looked like the kind of vagina that would be so pleasurable to be inside of that my sperm might 'sneak up on me,' so there was the pregnancy risk to consider as well. So I apologized and that having been the one condom I brought I said, "How about we 69?" Becky seemed equally happy to do that. So since she was still on all fours, I simply laid on my back on the carpet and positioned my face under her pussy and ass. I spread apart her ample ass cheeks and opened her vagina up displaying its full glory. I kissed and licked her clitorus and inserted my tongue in the hole where my penis had just been. Becky was moaning softly (I'm sure in hopes of our mutual friend not hearing) while she started fondling and licking my no doubt, latex-tasting, penis. It was not long before my previous hard-on returned. Soon Becky was blowing me in earnest, taking deep bobs, hands free, up and down my shaft. I continued to enjoy sniffing and tasting her pussy. I even made a point of licking and kissing the pubic hair growing along her labia majora.

We mutually satisfied one another for probably a good 15 minutes. As good as it felt, I wanted to concentrate on making sure Becky came, and It seemed to me that she had orgasmed twice within this time. So now I did start focusing on my pleasure and just how lovingly Becky sucked my cock. About a minute later I felt like I was going cum. As soon as her mouth put me past the point of no return I intoned, "Oh, there it is. Uggggh, you're gonna' make me cum." I then shoved my tongue back into her vagina pressed my nose against her asshole and ejaculated in her mouth. It was a powerful and copious ejaculation, but, this time, Becky swallowed every shot I fired into her mouth and throat.

I think a week later I found out that a good friend, Jake, who did go out with Becky and the group that Friday got a blow job from Becky on our friend's balcony. She just got on her knees, sucked him off, and spit his load off the balcony. Naturally, he wanted to know how far I got with the same girl the next night, so I regaled him with the above details. He remarked, "So she does swallow?" I replied, "Well, maybe she reserves that for when she's 69-ing." We both laughed. I am still good friends with Jake to this day and we still recollect about our shared experience with Becky.

So I suppose you could say I got 'sloppy seconds.' Now I don't begrudge Becky hooking up with two guys in one weekend. Hell, hooking up with two women in one weekend was always a kink of mine in my single days! It rarely happened, but when it did, it was magnificent. But I was also glad that I didn't cave into my primal temptations and fuck Becky without a condom when my attempt to use one failed. I wasn't worried about Jake having anything, but what about all the other guys we don't know?

In early 1998, I was a second semester junior a the University of Wisconsin, Madison. That semester I studied in London, UK. My study abroad program was of to a slow start: I kissed a girl on my program and took an Englishwoman I met, Vanessa, to dinner and the theater only to engage in fully-clothed, light petting and no second date!

However, I did reasonably well with women on my college campus in Wisconsin. To that end, I reasoned I might have some luck going to the University of London Student Union. University of London was the college that partnered with the University of Wisconsin to allow UW students the opportunity to study in the UK and receive credit toward our undergraduate degree(s). So I suggested to a buddy I had made, Eric, that we head to the pub at the student union. Eric was a nice yet somewhat quiet guy. For better or worse, he was my wingman. However, I was a better wingman to him than he was to me - doing all the heavy lifting. On this night, we spied two British coeds who appeared to be around our age. As was always the case, I was the one who would go up to them. I did and they were receptive. Eric followed, and the four of us hit it off. Their names were Aby and Kate. Covertly, Eric said he would only 'get with' Kate because Aby was too fat. I did not mind at all because while Kate may have had the conventionally better figure, Aby was prettier with beautiful, light blue eyes and pleasant features. As for her figure, I had been with plenty of gals by that time with similar builds. And I always enjoyed myself. She was not fat. She was merely on the short side with thick arms, legs, and a bubble butt. In other words, she might aptly be described as 'chubby.'

To his credit, Eric hit it off with Kate and took her back to his flat. I hit it off with Aby and took her back to mine. Fortunately, I had the room to myself as my roommate (not just 'flatmate' but the guy with whom I shared an actual room in the flat) was away for the weekend. Fortunately, Aby was different than Vanessa in that she was not bashful about getting undressed. We were both nude within 10 minutes of our hook-up. This hook-up was noteworthy to me because Aby was the first female I encountered with a totally shaved pussy. Any novelty, however, was nullified by the horrible job she had done. So many bumps, ingrown hairs, and knicks. It really would have looked better with hair. Aby had raven colored hair and a nice triangle of black pubic hair would have been a lot more enticing than these bumps and cuts. I noticed this because I was (literally) heading to go down on her. Flag on the field. She didn't want to do that on the first date.

No problem. We got under my bed sheets and I fingered her while she gave me a handjob. She had a tight vaginal opening and seemed to like my technique. Her handjob technique was great too. After about five minutes I orgasmed. My penis was aimed at her side and I ejaculated four or five big jets of semen on her side and my bedsheets below.

"That's sorted," was her all-too-British response!