So this is the story of the sluttiest thing I’ve ever done.
I was 22 at the time. I was just out of a 5 year relationship with my first and only high school girlfriend, and i was truly single for the first time since becoming an adult. Our breakup was less than amicable, seeing as how we were both trying to end our first relationship and had no real idea how to go about it. Needless to say, it was a rough patch, and without going too much into detail, suffice to say I was in the mood for some exploration. This led me to OkCupid. And OkCupid led me to, for the purposes of anonymity, Toni.
Toni was an older woman. Well, at least it seemed that way to me at the time. As a 22 year old man, 9 years seemed like a huge gap. However, this just added to her allure. I had never been with someone who wasn’t my own age, and she seemed so confident and sure of herself. Little did i know that this night would be the start of a long and lustful fondness for older women. Toni was my first match on OkCupid, and she sent me my first message. Her agenda was summed up very succinctly in 4 words:
“We should hook up.”
I was taken aback by this at first. How does one respond to something stated so bluntly regarding something so intimate? I thought that there surely had to be more to it than that. I probed, just to be sure:
“Oh we should, should we? Why’s that?” I asked. Trying my best to act coy but still get a human answer from her.
“Because you’re cute, and I’m wet.” She replied. Again displaying her trademark no-nonsense approach to conversation.
“Tell me more.” I said. “What are you wearing?”
A message appeared in my inbox. A phone number and a winking face. I added the contact and said hello. Suddenly a photo appeared, captioned simply, “too much.” And then appeared a photo of the most gorgeous pussy I’d ever seen in any circumstance, be it porn or real life experience. She had her black thong pulled to the side, revealing a gorgeous small labia that opened like a flower with her legs spread. Her pussy was bright pink, trimmed into the shape of a landing strip, clearly cared for with the expectation that she was going to get filled that night. Her fingers spread the lips apart, revealing a glistening clit. A clit sized perfectly for my fingers and my mouth to get around.
At this point I was satisfied that Toni was in fact a real person, whom showed genuine interest in my cock. But that still begged the question of whether i should accept her offer. I had NEVER done anything like this. I’d had plenty of sex by that point in my life, but always with people i knew. People i knew in person, or were in relationships with. Toni was a stranger. An enigma on the internet and I knew the risks that came along with that.
But I liked the risk. The danger made it all the more tempting. Perhaps she was a catfish. Maybe she was there with a group of thugs waiting to rob me as soon as i walked in. All I knew was that I needed some danger. I needed to be reckless. I needed to feel alive, and I needed to know for sure. So I accepted.
On the way to her house I could feel my heart pounding out of my chest. “What am I DOING?” I shouted to myself. This was so unlike me. I had always been the careful one, always the good child. Never drank, never got in trouble, was always careful about who I slept with. But here i was, driving to a womans house at 11pm in Downtown San Francisco (through the Tenderloin, no less!), to meet a complete stranger whom I’d been conversing with for all of an hour. What do I say? What do i do? Is this a date? How does this work? Am I going to die?
All seemed like valid questions at the time. And thankfully it was past 10pm so i didnt have to feed the parking meter when I arrived. The hallway smelled musty and old. I floated into the building elevator on a cloud made of adrenaline. My fight or flight instincts were fully engaged and I wasn’t sure which option to pick. I began to worry that there was so much blood pumping though my heart that there wouldn’t be enough left for my dick. However, what greeted me at Toni’s doorstep put me right at ease.
She was a shorter woman. 5 foot 3 to my 6 foot 2. She wasn’t skinny, but I personally love a bit of softness in the right places. Her thighs were thick and her breasts were massive. Her hair was perfectly curly and done up in thin dreadlocks. She answered the door in a blue spaghetti strap top, no bra, no pants, and the very well advertised black thong. I must have stared at her for longer than i realized because she started giggling and said, “Sooooo….do you want to come inside?”
“Hello”, i replied. In my standard Casanovian fashion. This did not seem to bother her, though, as she giggled again and pulled me inside. We sat down on the sofa in her living room and my mind desperately searched for something to say. Surely i was supposed to say something right? She clearly saw me for what I was: a terrified younger man in the presence of an older experienced woman whom i had no idea what to do with and no clue where to start because she simply whispered “don’t worry”, and leaned in for a kiss.
And it was an amazing kiss. A kiss that set the precedent for the rest of the night.
She slipped her tounge into my mouth and found mine. My hand slipped around her shoulder and pulled her into me. She tasted like mouthwash, which i appreciated. And she smelled amazing. No perfume or anything, just the clean essence of woman. Our tongues danced in each other’s mouths for a few minutes before i felt her fingers begin to slide my zipper down and unbutton my jeans. She opened me up and slid my boxer briefs down, where to my horror i discovered that i was not even hard yet. I’m a grower on top of that, so I thought my cock must have looked so disappointing. She did not miss a beat, however. She kneeled between my legs and slipped my whole flaccid penis into her mouth, and it felt otherworldly. I’d had blowjobs in the past, but they were nothing like this. She swirled her tongue around the head of my cock as she sucked. She slid her mouth up and down and held ger tongue firmly against my frenulum, allowing her taste buds to slide up and down, stopping just short of the tip to give my head another swirl.
It was at this moment that all my fears slipped away. Rob me, give me chlamydia, take a kidney if you have to, i didn’t care anymore. What she was doing to my cock was magical and i was in heaven from the start. There was also no doubt in my ability to get hard, because by now i was fully swollen and barely fitting in her mouth. I could hear her starting to choke a little bit, and just as i began throbbing she asked if I wanted to go into the bedroom.
I nodded. I was no longer preoccupied with finding the right words to say. Instinct had taken over. I felt every animalistic urge begin to take over me; we got to the bedroom and I grabbed her, spun her around, ripped off her shirt and pushed her onto the bed. She was very happy with what she had awoken. I leapt on top of her and started to suck on her nipples. I remember them being smaller than i expected, but her breasts were enormous and natural. I could sink my whole face into them. Apparently she had very sensitive nipples because after hardly a moment of playing with them she was almost screaming with pleasure. She begged me to give her what she wanted, she was emphatic about how wet she was, and she was not lying. I reached between her legs and i could feel her wetness dripping off of my fingers. I i slid one finger into her mouth so she could taste herself and she dutifully began sucking it and moaning. I realized that i still needed a condom, so i slid down and put my head between her legs. There was a condom in my pants pocket and i didn’t want to interrupt her pleasure while i awkwardly slid it on. So i distracted her by putting her clit in my mouth and lightly suckling on it (pro tip, fellas). She started screaming, gasping, and her hips started twitching. It was at this moment that i learned Toni was a squirter.
I’d never experienced it before. Suddenly she let out a screaming moan and tensed her entire body. I felt a warm, salty liguid pass over my tongue and run off of my face. This was obviously not new to her, because she didn’t mention it, but it did not bother me one bit. I laughed, wiped my mouth with my hand, and used her juices to lubricate the condom. I was throbbing and desperate, and jumped onto the bed between her legs. She was so wet already that i wouldnt have needed the extra lubrication. Nevertheless, my cock slid effortlessly into her. She was tighter than i had ever experienced. Or my cock was bigger than id previously thought, because i felt myself slide all the way into her pussy until i could feel her cervix push against my tip, preventing me from going any farther.
Toni’s eyes had rolled back into her head. She was trying to speak but could only get half-words out. I started thrusting, slowly at first. I was just getting an appreciation for how good her pussy felt. How warm and tight she was. Just soaking in the details. She put her legs around me and pulled my completely into her, looked me directly in the eyes and said “fuck me now”.
I obliged.
We fucked for nearly an hour. I started on top and alternated between slow, deliberate thrusts and hard, deep thrusts. The whole time she could only say short phrases like “please don’t stop” and “I’m cumming again”. In total she squirted 32 times that night. She claimed so anyway, though i don’t know how she was able to keep track in the state she was in.
After a while in missionary, she rolled me over and jumped on top. My cock slid so deep into her that i was afraid i might hurt her, but she rolled with the cervix punches and rode me harder than id ever been ridden before. After she wore herself out, i flipped her over and took her from behind. Hard at first, then harder, until she screamed that i could do whatever i wanted to her.
I obliged.
I fucked her with everything i had. I sank my cock as deep as it would go, i spanked her so hard that she yelped each time, but whenever i thought it might be too much she screamed out “harder! Give me what i want!”. And she kept cumming. Every few moments i would hear her moans get louder and louder and cresendo with a rolling scream as i felt something warm shoot onto my lap. Then she would go quiet for a moment and the cycle would start again. Over and over we went until i couldn’t manage another thrust. I let out a near scream myself and stopped, breathing heavily into my stomach.
I had no idea how i hadnt cum yet. It seemed like the nervousness that I’d felt earlier had actually become an advantage. As i caught my breath, Toni collected herself and pushed me back down onto the bed. She kissed me deep, tasting her own juices, and her face was salty from sweat. “You’re a machine”, she said, and slipped the condom off.
She then took her earlier blowjob and dialed it up to 11. She was gagging and diving onto my cock like she was on a deserted island and my cock was a buffet. She spat on it, took it in both her hands and rubbed it, she was filthy. I loved it. Finally i felt it building. I got harder in her hamds and started moaning loudly. She knew what time it was, and took my cock in her hands and pointed it at her amazing breasts. That sight alone did me in, and i unleased a torrent of cum onto her chest. Nearly two hours of built up cum flowed out of me, including the several hours of nervous horniness that preceded my arrival to her house. She couldn’t help herself and took a lick. “Mmmmm” she said. “Its sweeter than i expected”. I’d managed to completely coat her entire chest. Two GGG size breasts. I’m still proud of that.
She went to the bathroom to wash off and i stared at the ceiling. No longer confident that i knew what real life was. I was spent, and in the post orgasm glow, i had my moment of clarity. I regretted nothing. I had just taken a huge step in my sexual maturity. I’d done something totally reckless and had the best sex of my life as a result, and damn it felt good. I’d given my body and my mind something that it truly needed. A life lived without risk is a life you struggle to remember as time goes on, and though this was a simple act in retrospect, i opened up a whole chapter in my life. A chapter where i wasn’t afraid to take risks in order to get what i wanted.
Toni returned, we rolled a joint and basked in our glow. We ended up having sex one more time. She told me i was the best she’d ever had, and my confidence was higher than at any other point in my life. The weed really kicked in then, and i was looking forward to a well earned and restful sleep.
It was then that Toni informed me that her husband was arriving at 6am to drop off her son, so i actually had to leave. I ended up seeing her two more times. I wish i could tell Toni how much that one night affected the rest of my life.
Source: reddit.com/r/sexystories/comments/gqq0b9/the_story_of_my_first_internet_hookup