I’ve been laid up recovering from a cold and going through a bit of a dry spell lately, so figured I’d write up a few memorable sexual experiences I’ve had over the years.
For context: I am not exactly what most consider to be conventionally attractive. Fat, schlubby, bespectacled, and hirsute. Most people assume I work in tech. And yet, over the years I’ve managed to (somehow) have some truly mind-blowing sexual experiences with people who are way out of my league. I chalk it up to generally being kind, unassuming, and actually being able to keep up a conversation.
So this story starts at the beginning of 2020, right before the pandemic hit. I matched with someone on a dating site who definitely caught my eye – think half punk, half Parisian waif in look and style. We started talking and hit it off pretty well. I was initially a little hesitant because she was 7 years younger than me, still in college, but our chemistry was undeniable and frankly, she was gorgeous.
Thin and tall, with short cropped hair, sharp features, striking green eyes and (as I would later learn) beautiful perky b-cup breasts with pierced nipples and an ass that was the perfect blend of toned and shapely.
We started talking about the possibility of meeting when the pandemic hit, and spoiled our plans.
We kept talking though, started arranging virtual dates, and as the conversation progressed it got spicier and dirtier. I learned she was a brat and had a DD/lg fetish that she had me in-mind for. Eventually she started sending me videos and I started giving her instructions on what to do in them or how to dress – this Eventually lead to me picking out an outfit and sending it to her, and as thanks she put on a show for me wearing it. This became a semi-regular occurrence, that I was perfectly happy with.
As the lockdown restrictions were lightened, we again started talking about the possibility of meeting, but the lockdown and some other factors had taken their toll on her, and she ended up going home to California to stay with family before we could make it happen.
I kind of figured that was the end of that. We texted occasionally, but not frequently or regularly. We hadn’t spoken for a couple of months when, in the fall, she suddenly reached out. She asked if I was still interested in meeting up.
I was surprised. I honestly was never quite sure we would ever meet, or what would even happen if we did. I knew this girl was way out of my league so never expected much to come of our little virtual tryst.
She explained to me that, as many people did during the pandemic, she decided to start an Onlyfans to help with income and to help relieve frustration. She was interested in making some kink content for it (spanking, paddling, costumes, etc.) and knew that was my wheelhouse, and also had always felt comfortable with me and like I was a safe person to explore that with.
I of course leapt at the opportunity, though acknowledged in the back of my mind it was unlikely to be a sure thing. We talked about getting a room and me picking her up in the city where she lived and spending the night together.
I put together a bag of toys and treats, dressed in my best cardigan/college professor look, and headed up to her on the day-of, still half-expecting that I’d show up at her apartment and not hear anything.
It wasn’t until I had pulled up and saw her walking out that I started to believe. When she hopped into my car and gave me a massive hug I was slightly dumbstruck.
To back up: I had given her instructions beforehand.
She was to dress in a way that she could get away with in-public, but that “rode the line of appropriate.” Punk schoolgirl, to match my outfit.
Did she ever deliver.
Stockings up to her thighs, a tartan skirt that barely did the job, a white button-up that was nearly see-through, and no bra underneath, made all the more obvious by her pierced nipples. A collar and studded bracelets rounded out the look. An uber eats driver who was looking for an address literally stopped his car as he saw her getting into mine and shouted “damn girl you’re gonna have some fun tonight!”
I had told her to wear something that would make me struggle to keep my hands off of her. It worked. Riding in the car I was all adrenaline. “Is this even really happening right now?” Was coupled with an overpowering weight of more than half a year of unfulfilled desire that we could both feel.
She could tell I was flustered and enjoyed it. She started stroking my shoulder as we drove to the hotel I suggested, and I took it as a sign to do the same with her thigh, which she giggled about.
We got to the hotel, parked, and brought our bags into the lobby. The clerk at the front-desk gave us a look to indicate he had one or two ideas about why we were there (and probably thought either she was an escort, or we were shooting porn honestly. Half-right, I suppose. I did bring my camera and gear after all.)
The only overt indication he gave was asking us whether we wanted the top floor, with a little smile to himself.
We both got a massive kick out of it. There was only one other employee in the lobby and a middle-aged couple, probably visiting their child (we were right off campus). All eyes were glued to us as we made our way to the elevators. It was an electric feeling.
As soon as the doors closed, we looked at eachother, smiled, and kissed. It was incredible. I’m usually somewhat hesitant or restrained but it felt like we were old lovers reuniting. My hands immediately ran all over her, groping her and eliciting little moans and shudders as hers ran across my shoulders. We only broke when the elevator came to a stop at the top floor.
We made our way to the room, dropped our luggage. I took a moment to acknowledge this was all really happening and poured myself a glass of wine to steady my nerves. She sat on the bed and just eyed me.
We must have talked but I don’t remember what was said.
What I do remember is, within five minutes, grabbing her, bending her over the bed, roughly pulling down her thong and fucking her harder than I’ve probably ever fucked someone for the first time.
There was no subtlety, no buildup, nothing but pure need that had to be satiated. I can still picture her perfectly shaped ass bouncing as I slammed into her over and over.
Often I can take a while to cum. It’s rare it happens quickly or even at all my first go around. But this was entirely different. I can’t have lasted more than three minutes. The entire time she was making all sorts of incredible noises, reveling in how she had managed to turn such a sweet gentle figure into one that was roughly, animalistically, pounding her senseless. As she heard my breath quicken and my cock throb, she turned her head to look me in the eyes and gave me an incredible look, half helpless ecstasy and half wicked delight. That pushed me right over the edge. I grabbed her wrists and held her down as I thrust into her with all of my weight and came incredibly hard.
After I had finished, she rolled over and slid down the side of the bed, looked up at me, and said “thank you Daddy.”
We both laughed.
That was the first of many times we fucked that night and the following morning. Let me know if y’all are interested in a part 2. I also have a few other stories to share, including fucking a woman who had been faithfully married for 7 years, living with a retired alt/bdsm model, and a number of threesomes.
Source: reddit.com/r/gonewildstories/comments/t1duma/my_28_night_with_a_punkrock_dreamgirl_21_fm
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