(If you want to skip straight to the sex, scroll down to the first break. This is a long one.)
Back in the late 90s, I thought I was a god on the nascent internet. I hung out in all the right AOL chatrooms, visited all the right websites, and sysop’d all the right BBSes in my local area. I was 18, and I’d been reading erotica text files and hosting pornographic pictures on my own BBS for years already. That plus some built-in predilections led me to know that I was into spanking.
I also didn’t have a ton of friends at college. My roommate was cool, and there were some other folks I hung out with, but by and large I spent most of my time online. And, as you did with AOL back in those days, you would see people come into a chatroom, you’d check their profile, and you’d send them a message, hoping to start a conversation.
Even back then I’d learned from other women on my local BBSes that men online were generally assholes who only asked “A/S/L” (kids, ask your parents) and treated women like crap. I tried not to be that way, and I guess it worked, because one October evening I clicked on a profile that interested me, said hello, and struck up a conversation.
I don’t remember her username, but her name was Linda (real name changed). She lived about 1000 miles away and was 28. I had hidden my age because I wanted to come off as older and more worldly. (I wasn’t a virgin, so at least I knew how to pretend like I knew what I was talking about when it came to sex.) Apparently it worked, because we chatted for a few days before I finally revealed that I was only 18.
Linda didn’t seem to mind. She kept talking to me. We’d met in a BDSM-related chatroom, but she didn’t seem too interested in BDSM. I’d already explored that with the girl who took my virginity, and knew I was into it and wanted more, but I also wanted to talk to people and make friends.
As it turned out, Linda was a bit of a dork. She was into sci-fi movies and fantasy novels, she was single, she had a job at a largish firm (I don’t remember what she did, exactly), and she seemed to find me interesting.
And then, two weeks later, she dropped the bomb: she was planning to visit all her online friends in my half of the US, and would I like to meet her?
Look, at this point all I knew was her height (5’6), her hair and eye color (blond and blue), and that she was nice. My girlfriend had dumped me a month ago. Of *course* I wanted to meet Linda. In the back of my mind, I hoped I was going to get laid, but I was pretty sure she wouldn’t want anything to do with me. After all, I was a nerdy 18-year-old college freshman who was about 50 pounds overweight and didn’t have a car, a job, or very much disposable income. What could Linda see in me?
Because this was the late 90s and neither of us had a webcam, a scanner, or a digital camera, we had to trust each other that we weren’t hideous. We made plans for her to arrive on November 22 — we’d go see *Star Trek: First Contact* together (her suggestion) after she picked me up. She described her car, gave me her plate number, and told me she’d beep me (I didn’t have a cell phone) when she was about fifteen minutes away, so I could go downstairs and wait for her.
She was late. Protip: most people you meet from the internet are going to be late. It’s just a thing. But I saw her blue hatchback pull into the parking lot, and my heart leapt into my throat. I quickly stuffed a couple of condoms into my wallet — just in case, and they were my last two because I was too lame to go buy more (a friend had bought my last box for me) — said good-bye to my roommate, and headed down there. (I know, I know, I was supposed to wait downstairs, but I could see the parking lot from my window and I was only on the second floor. I could make it.)
When I saw Linda, I was… well, I was whelmed. She hadn’t lied: she had blond hair (shoulder length) and blue eyes, and she was about 5’6. She had unstylish glasses and was wearing jeans, a flannel over a shirt, and boring flat shoes. Her hair wasn’t styled; it was probably just brushed out of the way. (Once I saw her naked, I discovered that she had a bit of a tummy, but that’s okay, I like that.)
But then she hugged me hello, and I discovered that her breasts were quite substantial. My ex had had C-cups, and Linda’s were *way* bigger than that. At least, that’s how they felt against my chest.
Linda and I went to the movie theater across the street, bought our tickets, and took our seats. The movie was great; we both enjoyed the hell out of it. I’d scrounged up enough money to take her to dinner after, but she claimed she had a headache and asked if we could just get drive-through.
Well, whatever, it saved me some money.
—
I bought us both dinner and we went to her hotel (I think it was a Holiday Inn, but it’s not there anymore). She’d already checked in so we went up to her room to eat.
And then things got awkward. Linda laid down on the bed, on her stomach, her head at the foot of it, and for lack of anywhere else to go I knelt at the foot of the bed and rested my head on the comforter, looking at her. Neither of us really knew what to say, but at some point it became clear that we should kiss. Linda was an okay kisser, neither good nor bad, but I don’t think either of us knew what to do after that. I remember she’d taken off her flannel, and as we kissed I reached over to touch her breasts.
No complaints. And also, without the flannel to hide them, they were *definitely* big. Firm, too; my ex’s had been a little squishy (though I’m not complaining).
Linda and I made out for a while longer, and all the while I knew the moment of truth was coming. I was — and still am — self-conscious of my upper body, and once Linda’s shirt was off, leaving her in just her bra (it was pink, but pretty basic) and jeans, I knew my turn would come soon enough.
But I tried my best to stave it off. I got up on the bed with Linda and, when she took her bra off, I carefully worked my way around her breasts, figuring out what she liked and didn’t like. At that point I’d only been with one other person, but I’d read enough porn to know that not every woman is the same. Linda’s nipples got hard, and they liked being kissed and licked, and when I reached down to cup between her legs she pushed against my hand.
Good news, then. She was into it. Awesome.
At some point my jeans came off, leaving me just in my shirt and briefs (it was the late 90s; leave me alone), and Linda started rubbing my cock through the cotton as I opened her jeans (one-handed) and reached into her panties to touch her. My ex had had 70s bush action, but Linda didn’t seem to have that much hair. When her panties came off, I discovered that she didn’t shave, but her hair was short and blond and barely hid anything.
I approved.
Linda seemed to approve of me as well, because, with the help of one finger inside her and my thumb on her clit, she came shuddering and gasping out little nonsense noises.
She was ready. She was definitely ready. She was on the bed, legs spread, one knee up, nipples hard, cheeks flushed, and she absolutely needed to be fucked.
But, being responsible and lame, after I took off my underwear and knelt between her legs, condom in hand, I asked her: “is there anything I should know about, medically?”
Yeah, I know, I suck and there are a thousand better ways to ask. But Linda just shook her head.
Okay, then. Condom on, take cock in hand, line it up, and push in, slowly but relentlessly, until her clit is pressed hard against the base of my cock. She arched, her breasts shifting only slightly — like I said, pretty damn firm — and put her arms around my shoulders.
I was eighteen, and I was with a 28-year-old woman who had come to town just to see me, and she had amazing boobs and I was buried to the hilt inside of her. My mind went blank. I forgot everything I knew about technique, everything I knew about touching my partner, and just started to have sex. We weren’t making love, but I wasn’t fucking her, either. That was one thing that all the erotica had drilled into my head: you never start out as hard as you can.
Linda didn’t seem to mind. She was slick and soft, hot enough that I could easily feel her through the condom. I leaned down to kiss her and that seemed to work, because she arched again and moaned into my mouth.
My ex used to come silently — we had no choice; we used to fuck in my house while my parents slept. She *could* be loud, but we rarely had that opportunity. So a couple of minutes later, when Linda started making noises that told me she was getting close, my brain went *TILT!* and I sped up, pulling back quickly and thrusting hard into her. Her legs went around my hips, her heels digging into my butt, and there was no possible way I could hold off.
I groaned, shoved into her, and came hard enough that it almost hurt. It had been two months since the last time I’d had sex, and having a roommate in a small dorm room doesn’t afford a ton of opportunities for anything but cursory masturbation. So what I’m saying is, there was a lot.
Almost immediately after, I felt ashamed as hell because Linda had *not* reached orgasm. With my ex I’d always gotten her off first with my hands or my mouth because she took a while, and I hadn’t even thought to do that with Linda.
Quickly, before my erection could fade away, I started to fuck Linda again. This was the first time I’d ever done anything like this, and it wasn’t awesome. It was weird and awkward, and I had to go harder than ever to make up for the lack of hardness between my legs.
But it paid off. Linda moaned, arched, and came, and I pulled out almost the instant she was done. The condom went into the trash, and I got in bed next to Linda and held her in my arms as she gasped for air.
I guess I’d done a good job. At the very least, she didn’t throw me out. And, bonus, I’d kept my shirt on so she hadn’t seen my upper body. Sweet!
I imagine we talked for a little while after that before she told me she was tired from all the driving that day. I asked if I could stay with her, and she agreed. She brushed her teeth, I used some hotel mouthwash, we got back in bed, and she turned off the light.
That’s when I took my shirt off. It was too dark for Linda to see as she curled up beside me, one arm across my chest, and fell asleep.
So did I.
—
Morning came. I had no idea what time it was — my glasses were on the bedside table, and I couldn’t reach them because Linda was still half on top of me. I eased myself out, crept naked to the bathroom, and when I came back Linda was stirring. I snuck under the blanket, pulled it up to my shoulders, and kissed her good morning.
It was one hell of a good-morning kiss. Maybe I’d been better than I thought last night, because Linda’s hand between my legs, wrapped around my quickly-hardening cock, was a pretty big clue that she wanted more sex.
Again, I was a moron about it. I kissed her, worked over her breasts with my lips and my tongue, and slipped my fingers inside her (she was already very wet), but I didn’t go down on her. I was probably distracted because she was doing a very good job of not letting go of my cock.
This time, though, Linda wanted to be on top. She urged me onto my back and then pushed back the blanket. I had a moment of panic, but just the one, because Linda had thrown one leg across my hips and was hovering over my cock.
I ceased to care about my body issues and grabbed the second condom from the bedside table. (Hope springs eternal, right?) I got it on right the first time and then Linda sank down onto my cock until I felt her ass on my thighs.
If I’d thought last night was good, I hadn’t seen anything yet. Linda on top was the best sex I’d ever had (at that age, anyway). She would grind on me; she would rock back and forth; she would move up and down, sometimes while sitting up straight and other times leaning forward far enough for me to catch a nipple in my mouth and suck it or lick it.
But clearly Linda preferred to be sitting up straight, riding me, especially when I reached up and started squeezing her breasts — which, by the way, barely moved as she bounced. She put her hands over mine and squeezed harder, and as lame as I was I could still take a hint.
Linda came.
And came again.
And came *again*.
And to my sheer amazement, *I didn’t*. Oh, I was loving it, and the way her body grabbed at mine each time she cried out an orgasm made my balls tighten, but I was actually managing to hold off. Not gonna lie: I was pretty fucking proud of myself. My record for making my ex come was twice in one session, and here Linda was, working her way up the mountain again for number four.
This time, she was really riding me, grabbing her own breasts and pinching her nipples harder than I’d dared — my hands were on her hips now. Her weight slammed against me each time she came down — she was probably 150-160 pounds, so, not insubstantial. Her face was flushed pink, eyes half-closed, hair a mess and stuck to her forehead, and she was a goddess.
Something gave way at the base of my spine and the next time she came down, I thrust upward and our bodies collided. Linda came loud and long, and I came just as hard, my fingers digging into her soft thighs.
Linda, spent, flopped forward onto me, her breasts so big that it was almost impossible for her to put her head on my chest. But she managed it. My cock twitched, and she shuddered, but I didn’t have anything left. I reached down, and she rolled to one side, and I took the condom off and got up to throw it away.
When I came back to the bed, I noticed a *huge* wet spot right where our bodies had been joined. I was so blown away that I stood there, naked, ignoring my body issues, reaching down to feel the area around my cock. Sure enough, it was slick, but not with sweat.
Linda noticed the enormous puddle and flushed red. She made a break for the bathroom, but I just sat on the edge of the bed and chuckled. Hell, maybe I giggled. I think I might have had the giggles; I don’t really know. But for the first time in my life, a woman had come so hard and so many times just from fucking me that she’d left a wet spot on the sheets.
Awesome.
—
Linda came out of the bathroom and we hugged, but it was clear that she was done with me. She opened her suitcase and found some clothes; I put back on what I’d worn yesterday and combed my hair with my fingers. She said she had to get on the road; she had to meet another friend four hours away, and didn’t want to be late.
I felt an irrational spurt of jealousy. Linda and I had shared a bed and fucked — *twice!* — and she was about to go do the same with someone else? But then I realized I was probably not the first person she’d slept with on this trip, either.
Oh well. Whatever. A 28-year-old woman had come halfway across the country to fuck me — an 18-year-old overweight dork who pretended to be someone else in AOL chatrooms. And judging from the puddle on the bed — seriously, it had to be at least two feet in diameter at its widest point — I’d given her what she wanted.
Linda checked out of the hotel and drove me back to my dorm. She gave me her address and phone number back home and told me to keep in touch. We hugged, and then she headed out of the parking lot.
I went back up to my dorm room, intending to change, but my roommate said his friend had called and asked for help moving, so I figured “fuck it” and we went to help out. My roommate didn’t ask where I’d been, and I didn’t volunteer the information. I even stayed off AOL until I knew Linda would be home again.
We did stay in touch, and a few months later I went to visit her, but the sex wasn’t that great that time so it’s not worth sharing that story. By my 19th birthday, I’d lost track of Linda — she was gone from AOL, her phone was disconnected, and she didn’t reply to my letters.
Oh well. It was fun while it lasted.
Source: reddit.com/r/gonewildstories/comments/5aftu1/mf_first_aol_meeting_first_20something_first