A True Story about the time I went on a business trip to Chicago with my mom and things got a little interesting...
*Ding, the sound of the seat belt sign chimed as the captain made an announcement.
“Ladies and Gentlemen, we have started our final descent into Chicago. We should be on the ground in about 30mins. We hope you enjoyed the flight as much as we did and we hope to see you again very soon, thank you!”
As the stewardess passed through the cabin one final time to collect cups and all other trash, I caught myself sneaking in a little naughty peak as one of them reached over the seat in front of me. She was a long-legged blonde who I’d been fantasizing about for the past 3 and a half hours. She was maybe only a year or two younger than my mother who was sitting next to me reading the latest celebrity tabloid. I’m not usually attracted to older women but as a high school sophomore, honestly ever halfway attractive woman catches my eye.
Hold on one second, let me go back a little. I’m going to tell you a true story (or at least how I remembered it) about a weekend business trip I took with my mother when I was 16 years old. A little about myself to start.
My name is Chase, and like any other 16 year old boy my hormones were always raging. Anytime I would see an attractive woman wearing something that was revealing just a little bit of skin, that would be enough to get me thinking about the dirty things I would do to her.
Funny thing is I was still a virgin...
You could say I was pretty average in every way possible, I was about 5’9 at the time with average short brown hair and a little bit of muscle but not very much. Pretty average cock just a little over 6 inches but I was told by some of my football teammates I had a nice mushroom head.
I played football but as you probably guessed I was pretty average. I lived a pretty average high school life up until that point. I’ve never had a girlfriend before but I did come very close to getting to second base with Stacy, one of the freshman cheerleaders a couple of weeks prior, at a party. She was a cute young blonde that looked a little too much like Torrance from Bring It On.
Anyways, enough about my high school life. I wish I could tell a story about me fucking that long legged blonde stewardess in plane bathroom but that’s not the story, maybe another time. This story takes place on a weekend trip I took with my mother, we were headed up to one of her business conferences.
My mom, Claire usually worked from home but sometimes would go out of state on business trips. I had been dying to go on one of these trips with her, since she was always telling me how great they were. She always would tell me how she got to stay in these massive 4 and 5 star hotels in big cities like New York and Los Angeles for up to 2-3 days at a time.
Luckily for me one of those trips happened to fall on a weekend. So as you guessed I got to keep her company for 2 days while she worked. She gave me the choice to either stay home with my dad and sister or skip a day of school and go to a city I’ve never been before, obviously who wouldn’t take the second offer!
We had finally arrived at the hotel, it was literally in downtown Chicago with all of the tall buildings around it. We got in around 5:30pm and the hotel we’re staying at for the next two nights is massive! It was bigger than any other hotel I had ever stayed at in my life, and to no surprise since it was the weekend there were loads of people walking around the lobby checking in. As my mom checked us in at the front desk she turned to me.
“Bad news honey, they’re all out of double beds. Guess your going to be sharing a bed with me tonight..”
“How could they be out of double beds if you already booked ahead?” I snapped back.
This was just great, I had come all this way thinking I’m going to finally get to experience a 5 star hotel, sleep in a massive bed all to myself and than this happens. What a way to start the trip!
“Just kidding Chase! You should have seen the look on your face.” my mom laughed
Honestly I should have seen that coming. My mom is always playing simplest tricks pranks on me and as usual I’d always fall for them.
As we stood in the elevator on the way up to the upper floors, my mom asks: “what if they actually were out double beds? I guess you would have had to share a bed with your mom haha.”
“I would have gotten to snuggle up with my little Chase bear. Aww how cute!”
“Or do you sleep naked?”
“Mom come on really?!” “Just stop! Your being disgusting”
“See that’s how I know you do... you always get defensive when you know I’m right haha”
“ I honestly never do mom...”
For the record I actually don’t sleep naked. I was too afraid someone would walk in and catch me with my dick out.
We finally got to our room, 418B. As my mom opened the hotel room door I followed in behind her lugging both of our bags. The hotel room was a pretty standard layout. One bathroom with a double sink, huge mirror, big shower. Two beds face a wall with a tv on it. Near the window was a table with a chair and next to that on the right of it was one of those comfy chairs that you could sit back and put your feet up on.
“Which bed do you want Chase? I think I’m going to take the one by the window, the view really is amazing from up here.”
The bed closest to the window did have a really nice view of downtown with the Sears tower in the distant background. Unfortunately the second bed that was closer to the bathroom only had a wall next to it with a painting of… come to think of it, I’m not actually sure what it was a painting of.
The bed faced one of a one of those tall full body mirrors you would find in a teenage girl’s room, the perfect mirror for taking nudes in. Too bad I’m not a teenage girl so it really had no use to me at the time, or so i thought....
“I guess I’ll be taking the one with the view of nothing but a giant mirror.” I said.
As I fell on to the bed exhausted from a full day of travel. All I could think about was getting out of these clothes and rubbing one out. The picture of that stewardess still fresh in my mind. My dick had been aching for hours now and all I could think about was how good it was going to feel to cumming in the shower.
My ritual had been, after coming home from a long day of school, getting the absolute shit beat out of me at football practice for 3 hours, I would come home go straight to my bathroom, get completely naked and jerk off in the shower with the hot water running all over. There’s nothing better than being horny all day, than coming home getting completely naked and busting a huge load in the shower. I guess there’s no reason why I couldn’t do that here right?
“Hey mom, who’s showering first?”
“Let me go first, I’ll be really fast honey, I’ve been dying to get out of these clothes and this bra... you wouldn’t understand.”
With my dick literally about to explode I wasn’t sure how much longer I would be able to hold out.
“Ugh fine, I guess just don’t take so long.”
“You’re telling me! Would you do me a favor and call the front desk and ask them to bring up a couple extra pillows?”
I guess I’d just have to wait a little longer, I need to keep my mind occupied just a little bit longer. So I decided I’d take a look for something good to eat on the room service menu. Not too long later I heard the water stop in the bathroom. Finally, I thought to myself. I was about to just strip down right there and have a go while my mom was still in the shower.
I hear my mom crack open the bathroom door and say,
“Hey Chase, can you grab my little red bag out of my suitcase? It should be on the top somewhere I forgot to grab it before I came in here.”
I walked over to her suitcase, grabbed the red bag which had in it lotions and other beauty products in it. And walk it over to the bathroom.
“Is this it mom?” Pushing the bathroom door open...
As the door slowly swung open I saw my mom, standing there in front of the sink, her back towards me completely naked with nothing but a bathroom towel barely covering her breast and ass.
I’ve actually never noticed just how attractive my mom was and how well she took care of herself. She looked great for a woman in her early 40s, 41 to be exact. She had short straight shoulder length dirty blonde hair. She was a little shorter than me, maybe around 5’7”. She had a slim waist slightly slimmer than your average mom that was her age.
She had a rounded stomach with a tad bit of chub not really that noticeable though. Her hips were wide and she had thick thighs but they weren't fat, she worked out a lot since she was always home.
Her breasts were probably around a 36 dd cup. Nicely sized pink areolas. She had relatively fair skin with the slightest bikini tan lines since like I said she always had time to lay out by the pool since she was always home.
She had two tattoos, the one on her lower back was a tattoo of a small sun, I forgot what the meaning behind that one was. And the second was one those pelvic tattoos of a tiny butterfly. That one I had only seen a few times. Overall she was curvy but not much extra fat if that makes sense, her body really was perfect for her age. I always noticed men around her age taking peeks, and checking her out whenever she was out in public.
As she turned towards me, I could just see out of the corner of my eye in the reflection of those giant bathroom mirrors, the back of her towel open just slightly revealing the tan line around her perfect round ass. As she walked closer towards me the towel revealed more of her ass and with every step she took I could her ass jingle just slightly.
And as you could probably guess I almost came right there! I was already barely holding on and now this?
Honestly I shouldn’t have been sneaking a peak let alone been turned on by this. Like I said before I never really looked at my mom like this, but in this moment her ass just looked so good! Maybe it was my raging hormones again but right at that moment all I could think about was just how amazing her ass looked.
“Um, Chase are you going to give me the bag or just stand there with that stupid look on your face?”
“oh um.. yeah sorry, I um was just thinking about the um...”
As she stood there facing me, her ass was completely exposed to the mirror. It was almost like she knew I could see but she didn’t bother to cover herself.
Just as my raging dick couldn’t take anymore, a knock on the hotel room door.
“Honey do you mind getting that? It’s probably the pillows you called for.”
And just like that, it was over. I walked towards the hotel room door as my mom closed the bathroom door behind me. I thought to myself, did she do that on purpose? She was literally standing there in front of me not covering herself. She had to know her ass was showing! I opened the hotel room door grabbing the two extra pillows and thought to myself, thanks for ruining the moment asshole
I’ve really got to jerk off, otherwise who knows what will happen?
A few moments later, my mom’s round ass still jigging around in my head, the bathroom door opened.
“Your turn Chase! See, I told you I wasn’t going to be long!”
I quickly grabbed my clean clothes, and ran into the bathroom closing the door behind me.
“Finally” I said out loud. Stripping off my clothes I turned the shower on behind me. Now usually at home I run the water behind me letting it ‘warm up’ and browse through the web browser on my phone looking for something good to get off to. But at this point honestly anything would do! As I slipped out of my boxers my hard cock bounced out, fully erected. I would say it looked like the Eiffel Tower but my dick is only 6.5 inches long so maybe a mini Eiffel Tower?
I walked over to the sink stroking my dick in front of the huge mirror where I had just, a few moments earlier witnessed my mom’s bare ass. The images quickly came back to me. Watching myself stoke my own cock, I imagined what my mom’s perfectly round ass would feel like. Her soft skin rubbing up and down on my dick as I dry humped her smooth thighs.
As I stroked my dick faster and came closer and closer to cumming, precum began to drip out. I spit into my hand, stroking faster and faster.
AND THEN SUDDENLY!
The bathroom door swung open behind me!
Now the rule in my house is that there are no locked doors ‘safety reason’ so I’ve become so accustomed to just leaving the door unlocked. As long as the door is closed, everyone in the house usually knows not to open it and come in.
I spun around completely naked, my fully erected cock dripping precum in my right hand, phone in my left. My mother is standing there, eyes wide looking down at my dick. We stood there for what felt like a full minute (it probably was more like 10 seconds).
I see her eyes move up my body then back down to my cock which now at this point has a long line of precum hanging from it’s tip.
She smirks just slightly still looking down at my dick. I felt myself start to blush.
“Well then...” She says “I see you’re enjoying yourself”
“I forgot my phone right there by the sink and I thought I heard the water running so I assumed you were already in the shower, but boy was I wrong...”
“I’ll just grab it when your done”
I see her slowly walk backwards out of the bathroom. Just as she closes the door I swear she took one last good look as the precum drips onto the floor...
Well shit...that was embarrassing?
No. I thought to myself, that was hot as hell!
As I put my phone down next to the sink and walked over to the shower still stroking my cock. I stopped right before I got into the shower
“Fuck it! I’m just going to cum right here on the floor”
And just a few seconds later I shoot two, three, four long ropes onto the bathroom floor!
“Fuckk!” that had to be one of the hottest things that’s ever happened to me!
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