Fun Game, Fun Bet, and Fun Friend

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.

"It's unlocked Dave, come on in!" she said.

So, I opened the door, and wow. I wasn't really sure what to expect since her social media profiles had no pictures of her in a bathing suit or otherwise that would have given me a clue as to what her body looked like. However, she had indeed made good on the bet and was standing several feet back from the door completely naked. Her body was smoking hot. Much better than I expected. She was in her early 40's but I knew plenty of women in their mid 20's who would have killed for a body like hers. Clearly, she took good care of herself!

I did my best not to stare, but she literally said "Go ahead...get a good look. After all...you won the bet!" and stood there for a minute, with a big smile on her face. She certainly didn't need to tell me twice! I scanned from head to toe and the first thing I noticed was that despite being naked she had still done her hair and makeup as though for a proper date. That was my first clue she had something special in mind. After that, my eyes made their way down to her tits which were AMAZING. Perky, round and bigger than I would have expected for her frame. Her nipples were rock hard, pointing right at me. Her stomach was "yoga teacher flat", and then I made my way down and realized she had either waxed or shaved her pussy. It was completely bare. She had gorgeous legs, and then as I kept going I realized she was wearing high heels. High heels, despite being naked. I smiled, because I realized I was definitely getting some action that night.

"So...do you like what you see?" she asked suggestively. Between the hair, makeup and high heels, I could tell she was wanting to be a huge tease. Which was ok with me, since I realized that letting her do a little teasing would probably be pretty fun.

"I do! And I love your shoes!" I answered.

"Oh good. I wasn't sure if you'd approve but I thought they kind of made the outfit complete." she said.

At this point, I decided to be bold, and I walked right over to her and put one hand on her hip (the other hand was holding the carryout bag still) and leaned in to give her a kiss. She closed her eyes and leaned in to me a little, and gave me a really soft kiss on my lips. She drew in a deep breath, and I could tell the kiss had it's intended effect on her. I leaned in, and gave her a little nibble on her ear before whispering to her "The shoes look great. Now, how about if you put this food in the fridge and we have a drink?".

Really I just wanted to establish that the food was going into the fridge instead of on the table. I had brought Thai food and even though it smelled amazing, I was more hungry for her hot body than I was hungry for food. Plus, that had the extra benefit of giving me a rear view of her as she walked off to the fridge with the food. I'm sure she knew I was looking and she bent almost completely over to put the food in the fridge. Her ass was nearly perfect, and I could just barely make out her pussy lips while she was bent over. I guess I was staring, because I didn't even notice that she stood up and turned around. She grinned, knowing she caught me in the act, and asked if I would like a glass of wine.

I walked into the kitchen and she handed me a bottle of wine and a corkscrew while she got two wine glasses ready. I was playing into her teasing as well as I could, and I was playing it so cool that I think I deserve an academy award for my acting job. I acted like there was nothing out of the ordinary about me standing there, fully clothed, in her kitchen having a glass of wine with her while she was totally naked. I popped the cork out of the bottle, and poured us each a glass. I maintained solid eye contact with her as I handed her the glass of wine, and I could see the desire in her eyes. Finally, I let myself glimpse down and I saw that her nipples were even harder than before!

Maybe she caught me looking, maybe she just picked exactly that minute but she leaned over, and gave me a very sensual kiss on my cheek that felt like it lasted awhile. Then she nibbled on my ear a little, while I rested my hand on her hip, pulling her in closer to me. Finally she whispered and asked if I would like a tour of her place. I was hoping that the tour was going to end in her bedroom. Before I could answer, she took me by the hand and walked me through the house.

I was thinking the bedroom would be first, but it wasn't. This was where I learned the first surprise about Amanda. She lead me into her dining room, which had a large floor-to-ceiling window with a fantastic view of the Washington Monument and Capitol buildings. Well, you could see the top of each. Still, it was a nice view and plenty of buildings faced her building. And there she stood, right in front of the window, totally naked, pointing out aspects of the view. I stood directly behind her, with my hands on her hips and whispered "You love being naked in front of this window, don't you?" in her ear.

Instead of answering, she took my hands and moved them right up to her tits. Finally! I had been wanting to get my hands on them since the minute I walked in the door, and they did not disappoint. I cupped her breasts gently for a minute then I found her rock hard nipples with my fingers. She arched her back and let out a soft moan while I rolled her nipples gently and asked her how much it turned her on that the entire city could see her naked in the window. She didn't answer. She just moaned softly. I took her hands, and put them on top of her head and whispered into her ear to not move them.

She kept her hands still, and I moved my hand down to her hips. I whispered "I love playing with your tits, but I would hate to obstruct everyone's view..." in her ear. Now, I don't know if anyone was actually watching in the window but I could tell the thought of someone potentially watching was a huge turn on for her. She kept moaning as I moved one hand farther and farther down until I could feel how smooth her pussy was and wow, was it smooth! I slid my hand right between her legs until I felt her swollen clit. This time she drew her breath in sharply, and now there was nothing gentle about her moaning. I slid a finger between her lips, and she was dripping.

Now it was my turn to tease her, and I whispered "Wow, I didn't know you were such a naughty little exhibitionist..." into her ear. She moaned harder, so I whispered "Wow, do you think they can tell how much you're enjoying this?" and there was nothing soft about her moaning now. I switched hands between her legs, and started circling her clit with a finger on my other hand and moved my other hand up to her mouth and gave her my dripping wet finger to lick off. She anxiously took it in her mouth and started licking her juices off my finger. Apparently, she was a little wilder than I realized!

Finally, she spoke. "I'm going to cum!" she told me.

"Oh no you don't...not until you ask permission!" I said. Just to show her I meant business, I slowed my circles down just a little bit.

"Please don't stop! May I please cum?" she asked, breathing very hard as she did.

"Beg for it." I told her, realizing that she really enjoyed being a little bit submissive.

"Please sir! Please!" she cried out, as I sped my circles around her clit back up. "Please!" she said one more time.

"Ok. Cum for me. Now." I said, and she instantly moaned like she was having an orgasm, and halfway fell backward into my arms as her body writhed with pleasure. I kept circling her clit for the first part and then focused on helping keep her upright as her orgasm subsided.

"Wow, that was amazing." she said, as she turned to face me.

"Well, I bet everyone loved the show!" I joked, nodding in the direction of the window. She laughed, and then started unzipping my pants. When she had them unbuttoned and unzipped, she dropped to her knees and pulled my jeans and boxers all the way to the floor with her. My dick was mostly hard already, and it nearly hit her in the face as it sprung loose from my boxers.

"May I, sir?" she asked, as she looked up at me and smiled.

"You most certainly may!" I answered, as she smiled and then took me deep in her mouth. I could tell she enjoyed giving blowjobs pretty quickly. Some girls just immediately start doing whatever motion is their favorite while others really take their time and savor it. And Amanda really savored it. She wrapped her lips around me, and teased the tip with her tongue. She knew how much fun I had teasing her earlier, and now she was going to take her time and do the same to me. I certainly didn't mind.

She worked her way up and down with her tongue, moaning the entire time and taking a lot of pleasure in feeling my dick throb in her mouth. Pretty soon she had me moaning, just a little bit. However, obviously I didn't want to finish this early so I pulled out of her mouth, and stood her up. I kicked off my boxers and jeans, and pulled my shirt over my head. Then I laid down with my head up against the glass, opened up a condom and motioned for her to get up on top of me. She grinned, helped me get it on, and climbed up onto me. She seemed a little shy. After all, it was one thing to be naked in front of the big window, and another to ride my cock in front of it. However, she climbed right on top of it, as if she couldn't wait. I could tell that seeing her own reflection in the window was turning her on. She slid my dick inside her, and let out a huge moan. I started working my hips to help give her some motion and if anyone was watching, they got quite a show! She kept taking my hands and putting them on her tits. I could tell she had extremely sensitive nipples. Eventually she started rubbing them herself, while I used my hands to keep her balanced on top of me. I whispered a few more things about how naughty she was and how sexy it was that we were having sex in her dining room where all those people could see us, and she was ready to cum again in no time.

"I'm cumming! I'm cumming!" she cried out. I flexed my lower back to lift her up just a little bit. The extra pressure sent her right over the edge. She started whipping her hair around a little, as she moaned. I held out, for now. I probably could have cum then but I wanted to wait. She came hard, though, and it seemed to last and last. After what felt like a full minute, she finally slid off. Which was good, Im not sure how much longer I could have held out!

"Did you cum?" she asked.

"Not yet. I'm saving it. You want one more?" I responded.

"Yes please!" she said, and waited for me to tell her what position to get into. I put her onto her hands and knees. I figured now that the buildings across the street had seen her naked, seen her cum from my fingers, seen her give me a blowjob, and seen her ride my cock that now they see her take me doggy style, right? She was very excited when I put her onto her hands and knees, and a few minutes later I would learn why. Some girls think doggy style is ok, and others love it more than anything. Very little in between, in my experience. Well, she was apparently in the "loves it more than anything" category. I got behind her, and slid inside and she instantly dropped her front down to raise her ass more into me. This position hits a girls clit and her g-spot extra hard, and Amanda lasted all of about 2 minutes before she came again, this time even harder. She came hard, and basically fell into a pile on the ground.

I gave her a minute to catch her breath while I took off the condom, and got some lube ready.

"Did you cum yet?" she asked.

"Nope. Come here!" I told her, and she smiled and immediately got back onto her knees. I put a little squirt of lube, and took my dick in my hand. I had my back to the window, and knew she would enjoy putting on one more little show. After all that we had done, it took me about 30 seconds to get close.