Welcome to one of my stories! My ex-girlfriend said I should share some of these crazy stories with the world. At the time, I never bothered but now with the pandemic I have a lot more time on my hands, so...enjoy! I have changed the names to protect everyones privacy, but the rest of the story is 90% true and 10% filling in the blanks of minor details that I don't remember.
So, this one took place in the Winter of 2015. A friend of mine (let's call him Mike) invited me to a Superbowl party that he was throwing. Of course, by "invited", I mean "practically begged me to come". He had a new girlfriend (let's call her Sarah), who I guess had a lot more friends than he did. The party was at his house, and he was apparently worried that she had a ton of friends coming and he would look like a loser if he didn't have some guy friends show up. I had not met his new girlfriend yet but I figured it would be a decent time even though I didn't care much about the game. My favorite team had already lost and the thought of another New England championship was pretty depressing. Still, it is always fun to meet some new friends, and, one friend in particular would turn out to be especially fun!
I was somewhat of a latecomer to the party. At the time, I lived downtown and my friend had just bought a big house way out into the suburbs. I underestimated how long it would take me to get that far out and I actually planned to stop and buy food or booze rather than make something, which also took longer than I planned. In fact, by the time I found a few good things to grab at the grocery store and a decent bottle of wine it was practically time for kickoff. I parked, gathered my things and walked in. Mike greeted me first, and I figured out pretty quickly why he wanted me to come so badly. There were 10-12 people there, and it looked like it was four or five of Sarah's girlfriends who had each brought a boyfriend/husband but I was the only one of Mike's friends who actually made the trip out. So of course I acted like his best friend to help compensate some however, the lack of single females had me a little bummed out. That is, until I met Amanda. It turned out there was one of Sarah's friends who was there alone, having just broken up with her boyfriend a few weeks before.
Amanda was a little bit older than me, but was totally cute. I was in my early 30's and she had just turned 40 but she had taken very good care of herself. I would later learn that she was a spin and yoga teacher, and it showed. She looked a tad older but still had a smoking hot body. As memory serves, she was average height, maybe 5'6'' or 5'7" and had medium length strawberry blonde hair. She was no more than 120 pounds soaking wet and even though the sweater she wore that night didn't give any hints, I would later learn that she had a spectacular pair of C-cups. However, she did not seem like the flirtatious type. Between her serious demeanor and the age difference I never would have expected for us to hit it off but at the same time I was glad to have someone to sit with.
If you watched the game then you probably remember that Seattle blew the game on the last play. It was an exciting game for the most part though. I rode back into the city afterward and had almost completely forgotten about Amanda when a social media friend request showed up a few days later. It took me a minute to remember who she was, to be honest. She was certainly a beautiful girl but I didn't think she was into me at all so I kind of filed that one away under "Not going to happen" but the friend request was a nice gesture.
Now, let's fast forward several months. Mike and Sarah had broken up and I hadn't really thought of Amanda in awhile. However, one night I came home from a night out just a little bit drunk and started going through messenger to see who might be up for a little bit of flirtation. At first, I thought I was messaging a different Amanda. Maybe between the booze and thinking it was a different Amanda I was a little more flirtatious than normal but after a few minutes I figured out who I was actually talking to and was a little bit embarrassed. Still, she was flirting back and even though I didn't remember much about her I did remember she was pretty hot so I kept going! We had a pretty sexy chat that first night. I didn't manage to talk her into meeting up but I figured out that she was definitely more fun than I had given her credit for at first. For instance, one thing I learned that evening was that she is apparently somewhat of a nudist around the house and seldom wears clothes when she is home alone. I tucked this bit of knowledge away, and came up with a plan.
I wasn't sure exactly what to do, then the perfect plan landed in my lap. She initiated a game with me on a popular word game phone app, and I managed to beat her by just a few points. I initiated a lot of trash talk, and she totally took the bait. She told me she had let me win, and that she could easily beat me. So of course I asked her if she cared to make it interesting. She took the bait, again, and asked me what I had in mind. I told her that if I won, I wanted to come over and hang out with her, and that she had to dress like she normally dresses at home (totally naked). I really had no idea what she was going to say but she smiled, laughed, and said "Ok mister, and what do I get when I win?". I let her pick her own stakes and I don't really remember what she picked but I think we both knew I was going to win. She sent me a few smirk and wink emojis and agreed to my bet! Her only conditions were that "I wouldn't be weird" and "You cannot tell ANYONE", to which I told her I would do my best to not be weird and that I wouldn't say a word to anyone.
So we played the game, and of course, I won. She did her best to make it look like a close game but I really don't think she was trying very hard. I won by quite a few points, and sent her a message that said "Victory!!" with several wink emojis. She pretended to be bashful, and I halfway expected her to back out but she said "Ok, so, when are you coming over?". I told her I would come the following weekend, and that I would bring carryout from a popular place near her house. At that point, I decided to press my luck and I told her that I wanted her to answer the door naked and that per our bet, I expected her to be naked for the entire evening. I could just about hear her blushing over the phone but she agreed!
The weekend finally came and I was really excited to see what would happen. I figured my odds of getting laid were pretty good, so I made sure to bring some condoms but I was also not expecting sex. She might just be a huge tease and walk around naked for awhile like it was no big deal (like any other nudist!) and not let me get anywhere with her. She lived in a popular condo building not far from my place in the city. I walked over, stopping along the way for carryout. It felt like it took forever to get the food! Eventually it was ready and I made my way to her building. Usually building's like hers would have a pretty busy lobby area but I managed to be the only person in the vestibule when I hit the button for her unit.
"Hey there, it's Dave!" I said into the little speaker.
"Hi Dave! Come on up!" she answered.
"I'm on my way, and you had BETTER be naked!" I said.
I heard her giggle a little bit before she hit the button to let me in. I walked inside the lobby and got in the elevator. I remember thinking that I barely remembered what she looked like, other than her social media pictures. Still, I was excited to see if she would actually follow through with her end of the bet. On one hand, I thought the odds of her chickening out were pretty high but on the other hand if she weren't going to go through with it, wouldn't she just have told me to not come over?
Finally, I made it to her door and knocked. I heard her voice from inside say "Who is it?" in a really flirty voice.
"It's Dave!" I said, trying my best to imitate her flirty tone.
