Account Login
On ThePornDude Hall-of-Fame
I got my first BJ from an older co-worker
In the early '90s, I was about 20 and still a virgin, working full time as a file room clerk for a government contractor near Washington DC. I had a steady girlfriend (now my wife) who lived about an hour and a half away, and at that point we only saw each other every other weekend.
I had a female co-worker who was a notorious flirt. She was about 35 and on the chubby side, not really pretty but cute in her own way. She had a very fun and outgoing personality, and as I mentioned she was an outrageous flirt. When in the file room, she would do things like brush her hand against my ass while walking behind me, or bend over to look in a bottom file drawer when I was standing behind her, glancing back to make sure I saw her giving me a great view of her ass. I started returning favors, like letting my hand brush her ass if I walked past her.
One day, she was wearing a very pretty floral dress with beige pantyhose and heels, a very classic '90s office outfit for ladies. She came in to get a file and handed me a folded note. I looked at it as she bent over to get a file, and it read "I'm not wearing any panties!" with a smiley face. I wrote "Prove it"! and handed it back to her. She read it and got a little smirk on her face, then walked over to a spot in the room that couldn't be seen from the door. She turned around and pulled her skirt up from behind, pushing her ass out towards me and wiggling it. She was wearing nothing but her beige pantyhose, giving me a wonderful view of her bare ass, which sported a red heart tattoo on one cheek. I was both shocked and obviously delighted! After that for several weeks, she would flash me her ass anytime she was wearing a dress or skirt and hose, and a couple of times even flashed me a frontal view, where I could see her hairy crotch.
This continued for a couple months until one day she came in and handed me an accordion folder and asked me if I could file it for her. I glanced inside and it was a pair of her pantyhose in a Ziploc bag! She gave me a slow wink, mouthed "read the note" and motioned her head toward the door, then left. As I watched her leave, I noticed she was barelegged. I opened the folded note and it said "I just spent 20 minutes fingering myself in my car to get these nice and wet for you. Meet me in the stairwell by the loading dock now!" (This stairwell was rarely used by anyone but the maintenance guy, and he seldom left his office between lunch and quitting time.)
I met her at the bottom of the stairwell and she immediately pulled me to her and kissed me, her tongue quickly entering my mouth and finding mine. My hands went her her ass and I fondled and squeezed it as we made out. After a few moments, she guided one of my hands around to her crotch and pulled her skirt up, and I started fingering her pussy, which was dripping wet. Her hand went to my crotch, where she found my cock hard and ready. She worked to free it and broke our kiss to go down to her knees and immediately went to work on me, kissing and licking the head before working it into her mouth. My hands instinctively went to the back of her head and gripped her long, brunette hair as she bobbed up and down on my shaft. She pulled back long enough to look up at me as ask if I'd ever had a blow job before. I admitted that I hadn't. She smiled and said "You can cum in my mouth and I'll swallow it. Besides, I don't want you cumming all over the front of my dress!" followed by a slow wink. She took me back into her mouth and resumed sucking me. A minute or two later I told her I was going to cum and she pulled back long enough to say "Give it all to me, baby." She took me back into her mouth and after a few more bobs of her head I shot my load into her warm, wet mouth. She kept it up until I had given her everything, and used her tongue to make sure I was cleaned up as well as she could. She then stood up and kissed me deeply again for a few moments, pulled back and looked at me with a smile and said we had better get back to work.
The regret -- This was a one time occurrence. She told me the next day that she had taken a job offer closer to her hometown in Louisiana and would be moving in a few weeks. She said I was a cute and fun guy and she had loved flirting with me, and wanted to do something special with me before she left. She did flash me her pantyhose ass several more times before she left, and gave me an enthusiastic goodbye kiss on her last day in the office, but that was the last time I saw her. We did reconnect on Facebook about ten years ago, but both of us are now happily married and have made no mention at all of our little tryst.
I kept her pantyhose locked in my safe at home until I moved in with my wife a few weeks before we got married. I figured it would be tough to explain to my new bride why I had another woman's pantyhose sealed up in a Ziploc bag in my safe, so I used them to jerk off in and then sent them to the landfill, but if I close my eyes and think, I can still smell her scent.
I got my first blowjob at 15 from an older woman in her 60s who was divorced and
retired.
I had been doing odd jobs around her house for a few months. It was mostly mowing in the summer and shoveling snow in the winter.
She asked me if I would help her clean out her basement. One Saturday morning I went to her house and helped her carry a lot of boxes to be taken as trash. After, she
made me a nice lunch and paid me cash. The topic of if I had a girlfriend or not came up She asked me if I had a girlfriend and I told her no.
As I got ready to leave she asked me if I wanted to continue doing jobs for her. I said that I would. She told me that she enjoyed my company and then kissed me on the cheek and told me not to tell anyone.
She hesitantly began unbuttoning my pants
as her hand slipped in and touched my cock.
It felt so good. She asked if I was ok with what she was doing. She then kneeled down and pulled down my pants right to the ankles.
She looked at my cock and commented how nice it was. At first she licked and sucked on my balls and then she took my entire cock in her mouth. She started sucking feverishly. I knew I was going to cum so I pulled away. She asked me why I did that as said she wanted to taste my cum and it was ok to cum in her mouth. I knew that I had blew a few unmistakably good spurts of cum and watched as she swallowed everything.
When she was done, she stood up and said not to tell anyone otherwise she wouldn’t do that ever again.
I couldn’t walk I was so drained. She ended up giving me a ride home in her car.
There were a few other times when I was there she would have to tell me next time as she was busy with her neighbors,relatives or kids visiting.
She eventually sucked my cock a couple more times before she sold her house and moved to Florida. I lost contact with her after that.
My first blowjob from an older woman was when I was 14. I'd been cutting her grass that summer and she'd let me see her naked several times making it seem like an accident. Then one day she had me come in and she took her robe off and was naked. She asked if I'd ever had my dick sucked? I lied and said no and in no time she was on her knees sucking me off. Over the next few weeks she let me suck her big tits and she sucked me off a few times. And she was the first girl who let me fuck her tits and shoot off on them which I came to love. But she wouldn't let me fuck her.
Love the stories. If anyone has a story to add please do that is why we are here. We like telling and reading these stories.
My first blow job was from an older woman too. I was 16 working at a retail store for the holidays. On Friday nights, we got off work at 10pm and some of us would go to Perkins. D**a was mid 30s, average in the looks but had an amazing body, fake tits and a big flirt. Her husband was in the military and deployed in the Mid East. One Friday night it was just the two of us at Perkins. She asked me if I had a girlfriend. no. She asked if I'd ever had sex. no. We went back to her place. She gave me my first bj and we had sex. OMG! I hooked up with her for a few months until her husband got back and they got reassigned to FL. Fun times back then.
My first blow job was from my wife when we dated. She wasn't very enthusiastic about it at all. I learned to live without it.
Then I has a job, had a wonderful coworker, a 23 year old with 3 children. She was a great coworker, help out, never a drag. She needed some work done on her car, so I did it for her. When I returned it, she was greatful, and said she pay me back and what did it cost. I said don't worry, it's my good deed. She kept insisting so I asked what she gave the last person that worked on her car, she replied a blow job. She saw that she flustered me, she just smiled, threw one arm around my neck, gave me the sweetest kiss and with the other rubbing my cock.
She sat me in a chair, pulled my pants down and proceeded to give me a memorable BJ.
I would have left my wife for her.
Did you recommend more work to be done on her car?
Honestly it was so refreshing to have a woman play with your cock without any bitching. It was just as much as her attitude and willingness to please me as the actual bj.
Funny she met my wife twice, after the second time she fucked me. I'll never forget, she said you deserve some good pussy, cuz your wife is a cunt and I wouldn't be surprised if she is seeing someone. I thought that would be impossible as the woman just about hates sex. Found out later that she'd been seeing someone for about 4 years.
I don't have that problem any more.
My wife said the first blow job she gave was when she was a virgin and a guy asked her if she knew what 69 was.
She said, "No".....
He took her to his apt and showed her!
Yeah - she had a sick in her mouth before she had one in her pussy.
First bj was at work was from a 26 year old accountant. She was Hispanic petite cutie with a toned ass. Worked late with her one night and caught me staring at her ass when she bent over. Going red she said it's okay I know it's a fine ass. Telling her it was tight she asked if I wanted a feel. Pulling her in close I grabbed her ass hard with both hands. Hearing her breath hard her chest pushed out. Going under her skirt she had on a small thong. Telling her her ass was amazing she cupped my dick and said she wanted to see how big it was. Undoing my pants she freed my hard cock. Gasping she said it was bigger than she thought and went to town. She knew how to suck and was deep throating me hard. Pulling down her dress top I was met with her small brown breasts. Lasting as long as I could I came hard. Moaning and sucking down my cum she smiled and said she wanted to ride me but that would have to wait for another time.
That is one awesome co worker!!!
Great story! Made me rock hard when she was blowing you. I had a cute young admin assistant that used to bend over to file things and gave me a great view, including her thong hugging her hips as her pants slid down a bit. But we were both married and I never got the co-worker flirting or blowjob that you did. Thanks for sharing.
I'm sure I'm not the only guy in the office that she met in that stairwell, but I'm not going to complain, lol! I've had other co-workers over the years that I've flirted back and forth with, but nothing anywhere close to that experience!