First encounters - Older Women
When I was in high school, I worked retail at a hardware store. In the summer in the midwest where I grew up, it was hot and humid nearly all summer. It wasn't like it is today, where you walk aimlessly around massive Home Depot or Lowes, this was a small family run shop where we greated customers as they came in and led them to the exact thing they needed to fix whatever they were carrying. Inevitably, braless women with loose fitting blouses or t-shirts and low-cut collars would need things in the lowest shelves in the store. This was an opportunity for a post-puberty but still not a man teen to get a glimpse of those nipples as the customer leaned forward. I know this is pretty tame, but for a kid with a huge porn addiction, seeing the real deal was EVERYTHING.
Fast forward - first summer job after my first year in college, I worked construction installing in-ground pools. The corners of these beasts were always hand dug in the heat of the same blasted summer. This wasn't glorious work - it was trench digging hot and humid. It was hauling wheelbarrows full of concrete down wood planks to pour new concrete decks. Needless to say it was a 12-hour a day hardcore workout. I built muscle everywhere and put on about 25 pounds. I was in the best shape of my life and tan.
Every now and then I would be tasked with "opening" a pool we recently completed. This was a gift given by the foreman to the hardest working trench worker. I was rarely selected. It was my first year and frankly I was lowest rung on the ladder. But as summer was getting closer to the end - we opened more pools so I was selected. Now this meant clean work above the ground on the freshly poured cement. You'd get chemicals at the right amounts and use a long poled net with a skimmer to clean out debris.
The woman of the house was nearly always home. They often decided to change and get into swim suits inside their new pool changing rooms or their bedrooms which often were within eyesight of the pool cleaning. The women were rich and friendly. Good for many reasons - they looked great and they "tipped" when you were done. Tipping came in a variety of forms.
For me, I made more money opening pools than anything. Most women just flirted. Laughed and offered you tea, lemonaid or a drink. That said, I truthfully got blowjobs from two women and I got laid three times by great looking older women. In most instances that were as old as my mother. In all, that sumer - I had five of the most memorable encounters in my life.
It could be because I knew they all were much more experienced, so I was intimidated. I was also always really scared of having husbands, men, kids or someone walk in - unless they said they were divorced, kids were gone, etc. That said, because older guys would tell us stories and the bosses were always scary as shit, I felt my fears were justified. One said a woman was a complete psycho, called her husband while she was trying to pull off his shorts and told her husband he was trying to "r*p*" her. That was more of a warning story - but like I said before, the bosses were generally pretty merciless.
The first woman I got to experience was a really unbelievable blowjob - she came out with some tea and lemonade. She was really kind and the best - mostly because I was a little clueless. I will also say this - I never spoke about it to anyone. I hoped I would get asked back - and I never wanted anything to get back to the bosses that could get me fired. She was braless - lowcut blouse, tied off Daisy Duke style so her stomach was exposed. I think maybe one or two button - everything loose. As she leaned over she must have seen me staring down her shirt and she sorta spilled the iced tea/lemonade on my jeans. She starts wiping them off - and I got ROCK HARD - and I mean my cock was coming out of the top of my waist.
She giggles - oh my and apologizes. She blushes and leads me inside. We have to get those shorts off you to get the tea stain out. She is divorced and kids are gone (check.) We get to the laundry room and well, let's just say she was in complete control. She gets my shorts off and tugs my briefs clean off - there I am, sweaty, hard as a rock - and my cock is curved up like a banana. She taps the tip and says that looks delicious. She gets onto her knees and backs me up against the wall.
Her mouth is kinda cold, because she has been drinking iced tea and she is still holding a plastic cup with ice and her tea in the other hand. She puts it next to my foot and keeps sucking on my cock. She grabs a few ice cubes and starts rubbing my balls with the ice. She is massaging and sucking and as my cock hits a spot in her throat it sorta gets caught. I think she is going to gag, but she turned her head a little and took it past the knock and down deep her mouth goes right against the ice on my balls. HOLY SHIT - it was an amazing moment.
I started to cum and feel the cum bubbling up - i get onto my toes a bit - but suddenly she pushed her hand down onto the back underside of my vein at the base of the shaft and my orgasm subsided. Back in and out she starts again. This went on for a good ten minutes - each time stopping me. I know that doesn't sound long but at 18 years old - I swear I just about to cum maybe five times and every time she held me off. Finally she grabs my cock in her warm hand and cums up and kisses me on the mouth. She still hasn't really spoken to me. I am naked and she is still fully clothed - sorta - she pushed her tits into me through her blouse and they are warm and lovely. But she goes straight back down and swallows me whole. Up and down and is pumping me with everything she has - deep down onto my cock and then I just absolutely explode in the back of her throat. She holds me there. HOLD HOLD - each stream of cum squirts down into the back of her throat. She is squeezing and releasing my balls. It felt like a good six streams. She sucks and sucks and then squeezes the tip onto her tongue. She looks up - smiles and simply gives me back the shorts and says she has to go. It was amazing.
Fast forward - first summer job after my first year in college, I worked construction installing in-ground pools. The corners of these beasts were always hand dug in the heat of the same blasted summer. This wasn't glorious work - it was trench digging hot and humid. It was hauling wheelbarrows full of concrete down wood planks to pour new concrete decks. Needless to say it was a 12-hour a day hardcore workout. I built muscle everywhere and put on about 25 pounds. I was in the best shape of my life and tan.
Every now and then I would be tasked with "opening" a pool we recently completed. This was a gift given by the foreman to the hardest working trench worker. I was rarely selected. It was my first year and frankly I was lowest rung on the ladder. But as summer was getting closer to the end - we opened more pools so I was selected. Now this meant clean work above the ground on the freshly poured cement. You'd get chemicals at the right amounts and use a long poled net with a skimmer to clean out debris.
The woman of the house was nearly always home. They often decided to change and get into swim suits inside their new pool changing rooms or their bedrooms which often were within eyesight of the pool cleaning. The women were rich and friendly. Good for many reasons - they looked great and they "tipped" when you were done. Tipping came in a variety of forms.
For me, I made more money opening pools than anything. Most women just flirted. Laughed and offered you tea, lemonaid or a drink. That said, I truthfully got blowjobs from two women and I got laid three times by great looking older women. In most instances that were as old as my mother. In all, that sumer - I had five of the most memorable encounters in my life.
It could be because I knew they all were much more experienced, so I was intimidated. I was also always really scared of having husbands, men, kids or someone walk in - unless they said they were divorced, kids were gone, etc. That said, because older guys would tell us stories and the bosses were always scary as shit, I felt my fears were justified. One said a woman was a complete psycho, called her husband while she was trying to pull off his shorts and told her husband he was trying to "r*p*" her. That was more of a warning story - but like I said before, the bosses were generally pretty merciless.
The first woman I got to experience was a really unbelievable blowjob - she came out with some tea and lemonade. She was really kind and the best - mostly because I was a little clueless. I will also say this - I never spoke about it to anyone. I hoped I would get asked back - and I never wanted anything to get back to the bosses that could get me fired. She was braless - lowcut blouse, tied off Daisy Duke style so her stomach was exposed. I think maybe one or two button - everything loose. As she leaned over she must have seen me staring down her shirt and she sorta spilled the iced tea/lemonade on my jeans. She starts wiping them off - and I got ROCK HARD - and I mean my cock was coming out of the top of my waist.
She giggles - oh my and apologizes. She blushes and leads me inside. We have to get those shorts off you to get the tea stain out. She is divorced and kids are gone (check.) We get to the laundry room and well, let's just say she was in complete control. She gets my shorts off and tugs my briefs clean off - there I am, sweaty, hard as a rock - and my cock is curved up like a banana. She taps the tip and says that looks delicious. She gets onto her knees and backs me up against the wall.
Her mouth is kinda cold, because she has been drinking iced tea and she is still holding a plastic cup with ice and her tea in the other hand. She puts it next to my foot and keeps sucking on my cock. She grabs a few ice cubes and starts rubbing my balls with the ice. She is massaging and sucking and as my cock hits a spot in her throat it sorta gets caught. I think she is going to gag, but she turned her head a little and took it past the knock and down deep her mouth goes right against the ice on my balls. HOLY SHIT - it was an amazing moment.
I started to cum and feel the cum bubbling up - i get onto my toes a bit - but suddenly she pushed her hand down onto the back underside of my vein at the base of the shaft and my orgasm subsided. Back in and out she starts again. This went on for a good ten minutes - each time stopping me. I know that doesn't sound long but at 18 years old - I swear I just about to cum maybe five times and every time she held me off. Finally she grabs my cock in her warm hand and cums up and kisses me on the mouth. She still hasn't really spoken to me. I am naked and she is still fully clothed - sorta - she pushed her tits into me through her blouse and they are warm and lovely. But she goes straight back down and swallows me whole. Up and down and is pumping me with everything she has - deep down onto my cock and then I just absolutely explode in the back of her throat. She holds me there. HOLD HOLD - each stream of cum squirts down into the back of her throat. She is squeezing and releasing my balls. It felt like a good six streams. She sucks and sucks and then squeezes the tip onto her tongue. She looks up - smiles and simply gives me back the shorts and says she has to go. It was amazing.
6ヶ月前
