**Myself: Brian, 26 at the time. Her: Betsy, 26 at the time.**
“I know where we can meet.” She said, inside of AOL instant messenger.
“Where?” I replied.
There was no way she was coming to my place. She wasn’t single so her place was out as well.
“I have the keys to my company’s old office space in the Empire State Building.”
I had met Betsy in a random chat room on AIM. It was 2000 and that was a pretty common thing. We quickly relaxed we were both in New York City and had been chatting for a few weeks, random things, some cybersex and trying to figure out if we should actually meet. She had access to a digital camera and had sent me her picture. I wouldn’t say she was unattractive, hut she wasn’t my type. Soft, corn-fed midwestern blond girl is the best way to describe her. More curvy than BBW, very pale skin, giant boobns and as blond hair as you get get. Someone out there would have been totally into her physically but not me. But she was into me, I enjoyed our flirting and she was very good at cybersex. That was enough back then.
However, the idea of getting laid in the Empire State Building was too good to pass up.How many people get to say that? I found the idea way more sexy than I found her.
“Ha, that will work.” Was my reply.
“What are you doing on Tuesday?” She typed almost immediately.
“You. :-P” Was my witty confirmation.
Tuesday came and I waited for her at the Starbucks near the foot of the Empire State Building we had agreed on. I recognized her as soon as she walked in, though she since she hadn’t ever seen a picture of me she was scanning the room. She definitely was more attractive in person that I expected. Maybe this won’t be so bad. I waved at her. She smiled and hurried over to me.
“Hi!” She said overly enthusiastically as she gave me a hug. It is funny how, even back then, the comfort you have with someone you’ve only met online but have talked with extensively.
I got her a coffee and we had random nervous small talk crammed at our table surrounded by tourists from everywhere trying to figure out how to not get ripped off getting tickets to go to the top of the building.
“Are you ready to go up?” She finally asked.
This was my last chance to back out. If I went up with her I knew i would be cumming in her and I couldn’t just be a total dick and disappear one day on her. I looked her over again. She had some cute features. Totally not the girl I was ever attracted too but I’m ok with this. The experience will be something new for sure.
“Let’s go. I’ll follow your lead”.
We walked into the building and up to security. Turns out she was an admin at the company we were there to “visit” and they had just moved about a week before. So everyone at the security desk knew her. She explained me as a new employee that was going to help her clean up a few things before the end of the month. It is crazy to think how relaxed building security was pre-9/11 in NYC. Especially for iconic buildings like the Empire State. They let us up with no ID check on me and only her keycard. How times have changed.
We got up to the space, she opened the door and we walked into the office. There was literally a single desk, two office chairs and a dingy small loveseat that looked as if it was original to the building. I walked to the windows and took in the view of looking south across Manhattan. Definitely impressive from as high up as we were somewhere in the mid fifties. I heard her lock the door.
“No one will bother us here. Though I should get back to the office within the next hour.” She said as she was walking toward me while starting to unzip the olive pencil skirt she had on.
“Where do you want me?” She asked.
I considered my options. I was committed. I wanted to cum. But I really wasn’t feeling her physically, even as I was trying. But here we were. I looked around at the furniture, which was more depressing that exciting, and noticed the windows to the space all had deeply set windows which meant you could sit on the window sill.
“Go stand next to that window.” I commanded. Another thing that threw me about this situation is that it was anything but BDSM related. We had talked about BDSM on AIM and she wasn’t interested at all. My sexual world for the past 5 years was almost exclusively BDSM related. Vanilla sex was something i hadn’t done in a while.
She wrinkled her nose at my tone, a small warning, but went and stood next to the window as I directed. Her skirt now fully unzipped but due to her generous hips it was in no danger of falling to the floor.
“I’m so wet. My pussy is so sweet. I can’t wait to have you inside of me.” She wasn’t wasting anytime. The girl knew what she wanted and was very much the aggressor in this situation. We were the same age but my BDSM super power was not in play and she was a horny girl who knew what she wanted. She wanted to be fucked.
“Take your clothes off.” I said less sternly, with a smile. I knew what I wanted now.
She complied eagerly. Once she was naked all I could think about was “rubenesque”. I had way too much of a art history background to immediately think of anything else. He wide hips, large and soft breasts with giant pink nipples and the little belly she had really hit the look. Even though I wasn’t attracted to her, she was a naked girl in front of me, wanting me to do anything I wanted to her. I was rock hard.
I walked over to her, took her hand and brought her up on the window-sill. We were about a foot and a half from the floor now and fully within the window. Given how high we were there was no chance anyone could see us but I love the idea of being in the window with her.
“Get on your knees and take my cock out.” I said to her. She eagerly obeyed. If I pressed my back against the side of the window bay and she pressed her naked butt against the other side, there was just enough room for the two of us up there on the sill.
Once she had my cock out she looked up at me. Her blue eyes directly looking into my blue eyes.
“It’s all yours. Don’t stop until you make me cum.” I told her.
“But I want you to fuck me too.” She replied with a whine.
“Next time. I want to enjoy this first.” Which was true. I wanted to focus on having my cock sucked while looking out across the city I loved.
“Promise?” She said, still locked on my eyes.
“I promise.” I replied with a smile.
That was all she needed. She was off. As soon as her warm mouth hit the tip of my cock a jolt of pleasure filled my body. I hadn’t realized just how turned on I was. The entire situation, taken together, was amazing.
I will say the girl was very skilled with her mouth. As I looked over the city I heard her the wet suction of her mouth and felt one hand stroking my shaft in synch with her mouth while her other hand was cupping my balled. My jeans and boxers were now around my knees and I could feel her large soft breasts on my thighs, just above the knee. I have to admit that was also turning me on.
She sucked and stroked filling my body with pleasure. More than once she made me gasp, close my eyes and grab her head to slow her down as it felt too good.
“Slow down. I’m getting close.”
She did as told slowing down but sucking harder. Almost like she was trying to suck the cum out of me rather tha stroke it out. Whatever she was doing I was beginning to lose it. It felt amazing and I felt my pelvic muscles begin to tense as I knew my orgasm was approaching.
I realized we had not discussed where I was going to cum. My prefer at the time was to cum on the woman’s chest. With her large and ample breasts it would have been anyone’s preference. However she was too talented with her mouth. I didn’t want her to stop.
“I’m going to cum in your mouth. I want you to swallow every drop.”
She looked up at me and confirmed the request with her eyes. With that she begin to change her rhythm up. SLow, then fast. The tip of my cock never leaving her tightly clasped lips, even with her hand expertly stroked my shaft with a subtle twisting motion.
I reached the point of no return. I tried to hold my orgasm back a little longer. I wanted more of what she was doing. It was the best blowjob I had ever received, possibly still to this day. That lasted for a few seconds though. With a loud gasp I exploded in her mouth while my eyes were fixed on the city hall area. I heard her moan as the first string of cum hit the back of her throat quickly followed by a second and a third. She took each string well. She sucked it all down and didn’t let a drop out of her lips. She also never stopped her sucking or stroking which got her a fourth and fifth smaller string of cum. By this time my hands were on either side of her head, fingers in her hair, holding her to me as a grunted out my face of pleasure. She finished expertly sucking me dry, literally. This girl really knew how to suck a cock.
“How was that? Did I do well?” She asked with a smile.
I leaned back against the side of the window bay. My legs were weak and I was still floating.
“Holy shit… that was amazing. Where did you learn to do that?” I asked, genuinely curious.
“I know I’m not the prettiest girl. So I always had to make up for it with my ability.” She said proudly.
“I can see that. That. Was. Incredible.”
“Thank you. So you’ll come back for more?” She smiled.
“Yes, yes I will.”
We made plans to meet again, in the same place, two days later.
Source: reddit.com/r/gonewildstories/comments/bke3nt/mf_002_betsy_oral_sex_in_the_empire_state