Once upon a time AOL, Google, Craigslist and others were wonderful places to meet kinky folks that enjoyed anonymous sex. These lead to some incredible encounters with some very fun people. A few total strangers have been utterly remarkable, some not so much. I guess it helps that I’m one of those guys that simply loves licking pussy and doesn’t mind hours of nothing more. One of those experiences was in Nashville in the early 2000s. 

I’d been chatting with one young lady in a locally oriented room so I knew she was near. She’d answered someone’s question about whether any of the females liked older guys. She’d offered very credible reasons why we were more fun so I PM’d her. Long story short, I asked if she’d ever fucked a stranger she met on line and she said she hadn’t but wanted too but she knew what she liked and asked a few questions. Not many really but I guess I checked all the boxes. Some what surprising that one of her questions was "Are you married?" I always tried to be honest so told her I was. She just moved on to the next question.

She asked for a picture and I sent her one. I’d felt pretty secure in her answers so I was hoping she’d send one back. She’d told me she was a pale redhead and that she was shaved and instead of sending the picture she sent her phone number. I called her and it was certainly a female voice. It was then that I figured out her full turn on as well. When she’d picked up I said “Hi, is this Tara” Her full reply was “Yes Da--y. My address is ————, The back door is unlocked. My room is the first door on the right in the hallway.” Then hung up. 

It was a risk but I said (meaning it both figuratively and literally), “Fuck it.” I was there in about 20 minutes. The house was as she’d described. There was no car in the driveway. I parked about a half block down and walked back to her house, went around the back and as stated the back door was unlocked. My heart was in my throat as while I had fucked numerous young women I hadn’t known well it was usually as pick-ups and took them to my place or their’s or even fucked in a parking lot a few times. This was different. 

I went in and the door opened directly into a short hallway. I went to that first door on the right and it was ajar. No backing out now. I opened the door and there was “Tara” on the bed, no covering, bare ass naked, fingering herself. She’d told me she was a pale redhead and that she was shaved. All of that was 100% true but the first look at her face made me wonder if she was lying about her age. This far in I wasn’t about to ask for ID. I didn’t say a word nor did she. 

I stripped down and immediately went down on her. I’ll be honest, in a stranger situation, I almost always go there first. I’ll take a good sniff before fucking or at least deciding whether or not to wear a condom. I decided yes to the first question and no to the second. This was one of the tastiest, best smelling kitties I had ever been with. I’ve stated earlier and in other experiences here, I LOVE eating pussy. My favorite thing. This little fuck toy had one I could have spent hours licking. Though the room was dark save for the light of sheer curtains on the windows, it was one of the prettiest I’d ever seen. Who doesn’t like a shaved, inny pussy?

I stayed there down on it for at least a half hour. That time, a bit more later, replacing her fingers with mine and she orgasmed at least 4 or 5 times. On the last one before I entered her I got the “Oh God D—-y!” reaffirming her particular fantasy turn ons. That was enough for me. It also happens to be one of my favorites. I pulled away and before I could enter her she flipped over quicker than a cat and pushed her ass back at me. Perfect alignment I slid into that lovely cunt as much as I had, all at once. I was impressed with that happening so fast and the perfect alignment that let it be so quick.

You all know that doesn’t happen all the time. This time it was the whole cock, one shot, all in. She orgasmed a couple more times and I was getting really close. I’m usually a mix it up kind of guy but this was so hot I was just hammering away. I told her I was about there and she said “not yet.” pulled away, opened her night stand and grabbed a small dildo and a bottle of lube…she applied it to both me and her asshole and said “take it.” I sure as hell did. 

The dildo/vibrator went quickly into that now vacant, dripping cunny. Maybe 3 more minutes and I busted as hard as I had ever before. It had been a couple of days and it was a copious amount. She just made some harder grunting noises and kept pushing back on it. After a few minutes of slower strokes I pulled out and she made a total mess of her sheets. I swear that a full ounce of cum came drooling out of her asshole. Her only utterance was “God I love being ass fucked.” 

We lay there for about 5 minutes, totally silent. Then I said, “That was amazing. We gonna go again sometime?” she laughed and said “whenever you want but it’ll cost you.” Then the hairs went up on the back of my neck. “Oh shit, here comes the other shoe falling. She’s a hooker” 

Nope. I’d told her I was a nonsmoker in our chat. She said, “I don’t want to get up, will you go get me a pack of cigarettes at the store on the corner?” I said I would and she told me the brand. I go to the store to get what she asks for. The clerk was a busty redhead, sort of cute, probably 35 to 40. I tell her I need a pack of “Benson and Hedges Ultra Light 100 menthols.” She gets them and I pay. 

As she’s handing me my change she says, “Nasty habit. Those are what my daughter smokes. I wish she’d quit” I drive back to Tara’s house and go back in. As I’m handing over the cigarettes I tell her about the clerk and she says “Yeah, that’s my mom, she hates that I smoke.” We hooked up probably another 10 times in much the same way with a couple of the encounters being even wilder than that. 

One thing I did find out was that she really was 18, 19 actually. Also that she was bi and liked being fisted. I had her age verified about two weeks after our first play session. We had had another fun rendezvous and almost got caught. We were in a local park in the car and fucking. We had a cop pull up on us and while we had scrambled and got our clothes back on in time, he demanded ID. As young as she looked she was of course carded. After he left I laughed and told her I was glad she hadn’t lied about that because I had always wondered. She just laughed and leaned over and said quietly, "I would have done the very same thing even 4 years ago." I wouldn't have but she knew in my heart she wasn't lying about that eithe.r

That all leads to a question. Have you ever done anything that risky? Is anonymous sex that leads to a pure “fuck buddy” relationships something you’ve done or would do? How many other’s had a great time in the bad old days of AOL and other chat rooms?