This is my fourth and probably final true story from my past. It’s chronologically the earliest of them, happening when I was nineteen. The other three are in my profile, if you’re interested. I hope you enjoy this one and the others. This was an odd experience for me at that age and I still think about it a lot.
Names and minor details have been changed to protect privacy.
Thanks for reading.
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I was at the end of my 2nd year of college and I had a job/internship for a small tech-related company of just a couple dozen people. I was the ‘jack-of-all-trades’ hanging out there when I wasn’t in class, doing IT support, running errands, and any small odd tech jobs that needed to be done.
My boss was Andrea, a 30-ish nerdy woman without much style. She was frantic, moody, high energy, outgoing, a little weird, and honestly not super attractive. Slim but with a boy-ish figure, glasses, brown hair.
One day she turned to me and said, “Hey, wanna make an easy $50?”
I said, “Uh. Sure. What’s up?”
“I’m having a party this weekend at my place and I need a bartender.”
I replied, “I don’t know how to do that. I’ve never done that.”
“Oh it’s super easy,” she said, “Mostly just opening beers, pouring wine, maybe making a rum & coke, and then just keeping things tidy. The last time I had a party I didn’t have fun because I was stuck in the kitchen just keeping up with drinks.”
I really didn’t want to do it. It sounded like a drag and while the money was nice, I didn’t really need it that badly. I hesitated and she upped it to $65 and said no more than three hours.
The party was called for 8pm but she said I could just show up then because most people wouldn’t arrive until a bit after that. I had never been to her place before. It was a really nice apartment for a young urban woman. Two bedrooms with a huge open living space and a big outdoor patio. It seemed bigger than the apartment I grew up in with my whole family.
Andrea was dressed more feminine that I had ever seen. She had on a sleeveless blouse and a knee-length skirt. I got things ready in the kitchen while she ran around and did other stuff to get ready,. People started to arrive around 8:30 and it was a pretty mature party. A lot of work people plus a lot of people I didn’t know. Older people, couples, jazz music on the stereo and I poured a ton of wine for people. It was pretty easy and uneventful and very unlike any of my college parties.
As the evening wore on, the group got smaller, people got a little more drunk and loud, the music got a little louder and faster, a number of people moved out to the patio to sit and smoke and talk. It was about midnight and I didn’t have much left to do. Andrea was “feeling no pain” and she was flying around talking to everyone and laughing her head off.
I grabbed her and said “Hey, it looks like I’m done here I was gonna leave. Cool?”
“Oh right sure! I can pay you now.”
“You can just do it Monday. It’s fine. Have fun.”
“No, wait. My purse is right here!” She started looking around and then ran into her bedroom and then yelled to me, “HEY come here, I’ve got it!”
I tentatively walked to her bedroom door. She was in the far corner of the room by her nightstand going through her purse. Her room was nice with a huge bookcase of books, a big bed, and nice soft lighting. She held out the cash, and said “Thank you so much. This made my night.”
The way she was holding her hand out and just standing there made me have to cross the room and walk behind her bed all the way in the opposite corner. When I got over there I noticed a fair amount of racy stuff on her nightstand.
There was a dildo, a book about oral sex, a book of erotica, and I think maybe a smaller vibrator along with all the normal alarm clock, water glass, etc. I glanced at it maybe more than once and she was giggly and laughing in a happy way. “I hope this is the right amount,” as she handed me the cash.
“I’m sure it’s fine.” I was super nervous. It was weird to be in her bedroom and I felt like I was invading her privacy even though she clearly didn’t mind. I started walking back out but she stopped me.
Her eyes widened like she just remembered something important and exciting. “OH! HEY! Want to see something?! Close that door. QUICK QUICK!” She was so frantic and fast and excited that I kinda just did what she said. I closed the door and turned back to look at her across the room.
She pulled her skirt up around her waist. She was wearing no panties and was completely shaven.
I was frozen. She was giggling non-stop.
She grabbed her dildo and a little lube bottle and quickly got it ready. She put one foot up on her bedframe and while still standing started fucking herself. She oddly didn’t change her demeanor. She was still giggly and happy. “Come over here! Quick Quick!”
She laid back on her bed and I said “There’s people out there!” There were probably 8 or 10 people out in her living room and patio.
She said, “Whatever, they’re fine. They can’t hear anything and no one cares.”
I just stood next to her, having no idea what to do while she laid flat on her bed continuing to work on herself with her toy. “This is ok, right? Fun, right?” Giggles.
I nodded, which I guess was all the consent that was needed.
She grabbed my belt with one hand and said, “Come on! Take it out!” I was frozen and freaked out but I felt myself getting hard. She really didn’t have patience and she just started getting my pants open until my cock was out.
She laughed again, which made me feel weird, but then just wrapped her lips around it and starting giving me a blowjob while she continued with her toy.
After only about 30 seconds she said “how long will it take you?” and I replied “Um. Not long, I guess.” Not realizing that the idea was for me to just climax ASAP. She looked up again and said, “Ok. Finish quickly!” and she started bobbing her head more until I exploded in her mouth. She gulped down every drop, still twisting and moving the toy in and out of her pussy, which seemed really soaked. She held me deeply in her mouth until she was sure she had it all.
She looked up and smiled, laughed again, wiped her lips, and hopped up and pulled down her skirt. I don’t think she climaxed or even came close. I think this was just something to do.
She let out a laugh that was pretty loud. “HAHA! Fun! Zip UP!!!!”. Once I did she led me out of the room quickly and said “thanks again!” and I headed out. Not a single person seemed to notice we were in her bedroom with the door closed for all of four minutes maybe? No one turned their head at all as I walked out.
My head was spinning. I didn’t know how to feel. She was my boss, I wasn’t attracted to her, but I was 19 and I got a quick blowjob. I never told anyone. I honestly don’t think she had this planned. I knew her for two years and I think that she just did crazy stuff on the spur of the moment. I think she saw me glancing at the dildo a couple times and just went with it.
At work, I didn’t say a word about it and neither did she. It was like it never happened. I continued to work there for another year and she was a pretty good boss. I didn’t stay in touch with her but we’re facebook friends. She seems as frantic as ever.
Source: reddit.com/r/gonewildstories/comments/kryelc/mf_making_a_little_extra_cash