1. This one’s about an old roommate of mine. This was during college, he was helping a girl set up some furniture, bookshelves etc. Right after, she asked if he wanted drinks and they have a few. Right before she asks if they wanted to take this further, he accidentally sharts himself. He says “hold on I don’t have a condom” runs back to our room, showers his bottom half, runs back, and closes the game. Legen-waitfortheshart-dary.
2. I used to do some summer home remodeling small odds and ends. I was referred by my friends mom to paint a couple of rooms of a house of a family friend. Her friend was a recently divorced, mid 40’s, a little thick (but gorgeous face) and had a 20 year old son(living there but rarely actually there). I was 19.
I spent most of the first day prepping the 2 bedrooms. One of them was hers. It had 2 windows and a door for a patio so it took a while. Annnnnyways, the whole time I was working in her room, she stood at the doorway waiting on me hand and foot…offering beers, lunch, and awkwardly providing small talk. I was naive but the thought that she was seducing me didn’t go over my head, but I was nervous as fuck so I didn’t really show any signals.
After some corner/trim paint applied and a smoke break, I came back in the room only to see her buttoning up a pair of tight jean shorts. I could tell she just put a new blouse on and it was still unbuttoned showing her pretty huge but older droopers. She somewhat turned and said “oh dont mind me…” as I was walking out and I continued my work as she buttoned up her shirt. She made some comment like “probably not the first set of tits you’ve seen…ha…ha…ha”.
I laughed and kept working. The whole day I had a raging hard-on but was too scared to make any moves.
Day two, after a night of obsessing about the possibilities, and jerking my dick a few times I came back determined to show a sign of my lust.
I asked her a bunch of questions and got her talking about her ex and why they separated…how she’s coping…blah blah blah. Eventually she shifted the conversation towards my experiences and she asked if I had ever been with an older woman. I anxiously replied, “no, but i’ve always wanted to”….that was the ticket. It was game time.
It took me 2 weeks to complete that job which I could have done in 4 or 5 days. She way over paid me and offered to take me on a trip to Vegas.
3. My best friend works as a HVAC technician for a local company. He’s seen some pretty awesome stuff while working on the roof (like two people banging in the pool next door with the girl’s giant bouncing boobs in plain sight), but nothing compares to his MILF encounter.
He gets a service call from a very wealthy neighborhood. When he arrives, the woman that answers the door is AMAZINGLY attractive. They flirt a bit while he’s repairing some common problem with her air conditioner. When he’s getting ready to leave, she tells him that he should stay for a while and…you know, have some fun with her .
He panics and immediately bolts out the door.
While driving to his next call, his mind is racing and he suddenly realizes that he just passed up a once-in-a-lifetime opportunity. He quickly turns around, rings the doorbell, and she answers with a smile. They didn’t say a word at all, just got right to it. Apparently it was the dirtiest, most primal sex he’s ever had in his life.
4. I used to teach swim lessons for little kiddos at a gym. Did it my summer after senior year (18) and my first summer in college (19).
Started off doing group lessons – 4-8 kids of a similar level. Then I started getting scheduled private lessons as the kids liked me and their parents (read: moms) would want to have personal attention for their kids and an excuse to talk to me more.
I have to clarify that I lived in a very affluent area. The gym I taught lessons at was as upscale as you get — 5 pools, 3 stories, and lots and lots of cougars/housewives/women who divorced their husband and are now living large.
There were about 3 women (per summer) that were actively trying to get me over to their house for ‘private lessons in their pool’ for their kids. One woman actually went so far as to request “adult lessons” with me (these are usually reserved for adults who CAN’T SWIM, and are very hard to teach). She didn’t need lessons at all. We spent the entire time working on her ‘form’ by me showing her how to do a front crawl, which entailed me holding her in the water. She’d purposefully squirm and try to get my hands to awkward places.
I was seeing my now-wife at the time. I was tempted, to say the least. The great part about it is that for my $9/hr job I usually received about 20-25 in tips. These women were all mid-30s early 40s, and clearly wanting it.
5. My friend was hanging shelves for this woman in his neighborhood as a favor. Afterwards, they sat down casually, just taking a break. She offered him a drink or something. And then she went in for it. She is hot so he rolled with it. It was a one-time thing — the exertion and post-handiwork satisfaction was hot for them both I guess.
We now call this kind of situation “hanging shelves.”
6. Does seduced by a couple count? I was 24, doing some computer work at a couple’s house that I had know for 10 yrs (friends of my parents). I always thought the wife was hot since I was 14. The husband was older then her (she was 44, he was 55). I had been over their house a few times fixing their computer. They followed me into their den, where I sat down in front of the computer. As I clicked the screen saver off, there were sexy pictures of the wife dressed in lingerie, paying with herself on the screen. They were both behind me, and feigned suprised, and she scolded him for having those up and letting me see them. He took control of the computer, and asked me if I liked what I saw. I nodded dumbly and said yes, I thought they were pretty hot. She asked if I would be interested in seeing the real thing, and I said yes. To make a long story short, she took off her top, and asked if I liked her new tits, which of course I did. She asked me to tough them to see if I thought they felt real, and I looked at her husband for the first time, and he was grinning and said “go ahead”. I squeezed her tits, and played with her nipples which caused her to groan. She reached over and felt my hard cock in my jeans, and asked if i wanted to fuck her in front of her husband. I ended up fucking her several times in front of him over the next few months, and he joined in a few times. I really enjoyed playing with them , as she liked to act like a slut in front of him.
7. I worked as a pizza/food delivery guy for a local Italian restaurant when I was 18. They mostly had repeat customers that order from them all the time. So after a while I knew most of our customers pretty well. There is this one blonde woman, probably in her 30s, works in an office building, I often deliver her lunch to her office, and then later deliver dinner to her apartment. She lives alone and seems to have low self esteem issues, as she always wore heavy makeup and perfume, even though I don’t think she need that shit to look good. I think she isn’t too popular at work too, as no one ever spoke to her while I was at her office.
Anyway, one night after I delivered her food to her apartment, she asked me if I had time to help her with her computer, promising a good tip. I said sure (I was known to be a computer geek). So while I was fixing the computer, she brought me a drink and sat really close to me, her boobs touching my arm. I instantly developed a boner and she noticed. She smiled and started to touch me, then she asked me if I wanted to have sex. I agreed. The rest was history. After that, whenever she got lonely, she’d ask me to stay a while after I deliver her food. Eventually I had to quit working there to go to college in another state, never seen her again since then.
Oh btw, she tipped me really well. She used to tip me $5 before the incident, which was already awesome tip for $10 food and 1 mile delivery. After the incident, she would tip me $10 and sometimes even $20 per food delivery.
8. It was in August a few years back in Boston. I had just returned to working as a pizza delivery person after needing a few months off from a car crash. The car crash was a horrific moment in my life, but it led to a unique health issue that actually worked in my favor on my first day back. You see, I had some spinal trauma that led to a medical condition called a priapism. Essentially, I had a hard on that would not quit. Ever. Fortunately, and unfortunately, I have a long and thick member that is noticeable if erect. So this led to me trying to hide it as best as I could on my deliveries that night.
As the night was winding down, I was placing my last set of deliveries. On my final order (thank God it was my final order), I was met at the door by a slightly tipsy and really hot redhead (for those wanting more info… Young… Maybe 20 or 21, I guess 21 since she definitely had been drinking, though this is a college town she could probably have been 19 and gotten drinks because she was pretty.) A solid 8 out of 10. She invited me in because she couldn’t seem to find the money on her anywhere. Now, up until this point I had been avoiding being fully seen by any of my customers. I had to sort of hobble in hunched over slightly because I was trying to hide this never quit boner. The fact that she had a huge rack and had a really cute girly voice wasn’t helping.
She beckons me to follow her upstairs and I stupidly say that I was fine with waiting at the door. What she said next made it all feel like I was in a dream: “Don’t be shy. I can see you have a boner. If you come upstairs we’ll fuck your brains out.”
Wait a minute… we?
I stood there slack jawed as she grabbed my hand and led me up the stairs and into a bedroom where I saw a completely naked brunette. (At the time she didn’t remind me of anyone famous, but now I’d compare her to Alison Brie of Community.) She was spread eagle on the bed and her wrists had been gently tied with soft cloth to the bed posts. (I found out through pillow talk afterwards that the two of them had been going at it for the past hour after a few drinking games.)
The redhead says to me “Take off your pants.” which I do in the fastest movement I have ever performed in my life, my hands shaking with nervousness. The redhead says to the brunette: “Is he acceptable?” as the brunette sizes up my huge raging hardon. She says, in a quiet whisper “More than acceptable.”
The redhead starts taking off her clothes, I finish taking off mine. The redhead guides me to the bed and I was going to go down on the brunette but the redhead says “I already took care of that, get to fucking.” Well… I pounded the everloving holy hell out of that girl. The redhead was making out with her most of the time and some of the time I’d be making out with the both of them. I climaxed after a few minutes of this and finished on the brunette’s chest. The redhead just lapped it up and made out with the brunette.
The redhead said “If you want to stick around and fuck me too when you’re hard again, you can.”
I told her she didn’t have to wait and, as if a priapism was a superpower, showed her I was still boned up and ready to go. We uncuffed the brunette and I laid down. The redhead rode me cowgirl style while the brunette sat on my face and made out with the redhead.
All said and done and two hours of fucking, sucking and coming later we were all spent. They let me stay the night, I slept a deep sleep in the middle of the bed with the two girls curled up to me on either side. It turned into a relationship for the next few months until the redhead started getting jealous thinking I was focusing too much on the brunette and the brunette on me.
In closing… I was told that they ordered a pizza that night and if they thought the delivery guy was cute enough, they entertained the idea of inviting whoever it was in. At the last minute they backed out… But then when the redhead saw I had a raging boner, she reconsidered for the both of them.
Best few months of my life ever, so far.
9. When I was working for an air duct/carpet cleaning company at age 25, I was sent to a nice house in a ritzy neighborhood for some air duct cleaning. The lady who answered the door was in her 50s, blonde-going-on-white hair, small and kinda frail looking. So in this job I’m supposed to go through the house and air clean all the vents while the main vacuum is attached to the HVAC. So I’m basically going through the whole house, room by room.
She is following me around and talking about how her husband is never there and he is away on work, how he always works and she hardly sees him. Of course its playing out Hustler in my mind, but I don’t let anything on, I keep professional and just make harmless work-related jokes.
Well at one point I’m downstairs working on the A/C unit itself, there is a washer and dryer in the same room, and she comes down wearing something totally different. Its like a pajama thing, but her legs are showing. I just kind of give her a look like “OH HAI” and she leans up against the washer and proceeds to talk to me about harmless stuff. There was definitely a VIBE going on, but for the life of me, I couldn’t follow through with it. I was friggin 25, for all I know, this dude could come home anytime. Its not worth it. So I just keep on acting like I don’t know anything and she obviously picks up the signal and lets me do the rest of my work alone.
10. Haha, oh man you guys are not going to believe this.
One of my best friends, who is also a swinger, told me how he got into swinging. He worked as a delivery boy for a pizza place when he was 18. His boss was really cool, and would always smoke with him and shit. My buddy got to know his wife really well also, and they would always invite him over to smoke and drink.
One day, my buddy is delivering a pizza that his boss said is for a friend of theirs. He told him to give them the pizza for free, and they’ll also tip him. He gets to the door, and a women approaches wearing nothing but a robe. He said she was middle aged, and really good looking. She invites him in to get his “tip”, and the house is full of naked people. There is a swinger party going on at his bosses friend’s house.
So the woman asks if he wants to stay and party, and my buddy is a little wary of the situation. Then, out of nowhere, his bosses wife comes up to him, also wearing a robe, and tells him if he stays she’ll suck him off. She said his boss wanted my friend to get with his wife because it turns him on.
He ends up getting a bj from his bosses wife, and gets a great introduction to the swinging community. To this day, he will still sleep with this guys wife while the guy jerks off in the other room. I didn’t believe him until he showed me the pictures she sends him all the time of her naked, sticking things inside of her. I know both of these people, and after meeting them it totally makes sense. Crazy fucking world we live in.
11. So, I’m the female in this case, and did the seducing.
I had been in 10-year relationship with this guy, right out of highschool. He’d ditched me about 3 weeks before, after taking all my furniture, my car, and my cat. Asshole even took my paper plates and salt and pepper I’d stolen from Wendy’s…the only thing he left was my clothes and some toiletries. I suspect the chick he ran off with, who I had worked with for a while, came in and stole some of my lingerie and my good make up, and I KNOW the bitch took off with 3 good pairs of shoes. Thankfully, I’d kept a separate bank account.
So, I was having a good pity party in my empty house, I ordered Chinese food. Pig out session planned, with Ben and Jerry’s in the freezer for later. I was stressed and feeling terrible, it all just caught up with me.
The chinese delivery place is in walking distance, and usually I would walk, but it was kinda cold and I just didn’t want to leave. So I called it in, and this time the delivery guy is this good-looking guy. I think he’s a friend of the owners, he’s in his late twenties, I’d guess. We never got that far…I know he was a musician in between jobs and would help them out by running deliveries.
So he shows up, slightly scruffy and with his baseball cap, kinda cute in a bookish way. I’d seen him before, he was always nice. I forget exactly how it happened, but I invited him in cause I stupidly didn’t have all the change, he would always hover in the doorway before, so I get my purse and he asks what happens. I tell him about the asshat moving out, stealing my shit, and he was genuinely empathetic. We start talking, and all of a sudden it’s a half hour later, he says he needs to call and let them know he’s running late.
I don’t know what happens during the convo, but he’s not rushing out to do another delivery, and is still asking questions. Just…nice, you know?
I guess I got all down, and I was alright, in my head, but he kissed me, said I looked so sad. And it was such a sweet kiss, just a light one, but I grabbed him and pulled him back.
I don’t know how it happened, but it was just all hot sexy time from there. He kept saying he should go, and I kept kissing him, undoing his pants, pulling off his shirt, undoing mine. After a while he stopped saying it, and the sex wasn’t great, but it was good enough. Plus, he made me feel amazing, wanted.
He shared the cold chinese food with me, which was awesome, and left about 3 in the morning. I called probably 2x a week for orders the next 6 weeks or so, and he wouldn’t deliver every time, but we never took it outside of that..I would call late at night when they were closing so he didn’t have to go back to work.
After that he moved to Memphis for a gig with a group and I never really talked to him again.
12. One year, while working as a delivery driver for a well known pizza chain, we were told by our managers that delivery drivers would be allowed to dress up for Halloween if we wanted. I think it was against corporate policy, but the food handlers didn’t care, and the managers wanted to do something nice for everyone who was working on Halloween, instead of being at one of the crazy frat parties that were going on in the area. I believe the food handlers got free pizza, we got to either dress up or get free pizza, one or the other, so I chose to dress up in my Indiana Jones costume. I figured, hell, might as well give some kids whose parents are lame and take them out trick or treating during the day a shock.
So I get sent on this delivery run. 2 pizzas, and a bottle of soda. I ring the doorbell of the house, the porchlight flips on, and this fucking gorgeous 20-something blonde answers the door. Holy shit. I had to consciously think: “don’t drop anything, asshole!” This chick goes: “Oh, my god!” I smiled, and I said something like: “Lost Ark pizza!” Chick pays, and goes: “Wow, that’s an amazing costume!”
I thanked her, and she goes: “I want to get a better look at it, but it’s so cold outside, you must be freezing. Come in, come in!” I come in, and she shuts the door behind me. Then, it’s the usual barrage of questions I get about the costume: where did I get this item, that item, how long have I been doing this, etc. After that’s all over, she goes: “That’s pretty awesome. I’ve always had the hots for Indiana Jones.”
Fuck. To understand my next statement, understand that this bitch had a goddamn fucking gorgeous rack, beautiful face, not too shrill but not too manly feminine voice, pretty legs…yeah, I got me an eyeful each time I handed her a piece of my costume to fondle. Hat, whip, etc. So by this time, I was just struck dumb and gobsmacked, floating around on a cloud, so I said: “Well, he’s right here!”
Alright, there goes my job. That’s what I thought. Wonder if so and so’s is still hiring?
She goes: “Well, my parents won’t be home for about an hour … ” she sticks her finger up to her mouth, and says: “Will you leave the hat on?”
Yeah, I left it on. Girl was a dynamite fucking lay, too. Oh, god. I had to make up a story as to why I was gone so long when I got back to the store, something like: “I had to stop for gas, but there was a line of people in the store buying stuff…” I still thought I was hosed, but my manager bought it.
13. As a landscaper/gardener I was working an area with lots of large houses and properties. When finishing up a job, all sweaty and worn out, a tall blonde woman probably in her late thirties came walking down the road in red heels and denim booty shorts. She was carrying a tray with a jug of lemonade and two glasses. Not thinking I started to climb in my truck to leave. She saw and started to hurry down the road and because of heels she slipped and fell. I immediately hopped out of the truck and ran over to her aid. She was happy that I helped but embarrassed. I told her there was no need to be embarrassed and that anyone would fall wearing those heels. She laughed somewhat awkwardly and I picked up on it right away (after being so oblivious already.) She admitted she was embarrassed for coming over with the intention to seduce me. She also admitted the lemonade was spiked and she was going to use the drunkenness as an excuse for me to come over cause I couldn’t drive.
This is where I slipped my hand down the back of her pants and walked her back to her front door and we proceeded to fuck like rabbits in her living room and by her backyard pool without talking any further.
14. Happens all the time! I worked as a service technician (residential phone man) for BellSouth in the late 90’s for three years before taking another position. I was hit upon numerous times by women of all ages. I was 23 at the time and even had to leave a house once. A girl in high school came into the room I was installing a phone jack with nothing on but a towel & wet hair. She was very up front with her intentions… No one else was home (the mother had got to the store) so I was in a very bad position… Luckily I just had completed my work and said I had to get to the next job. There are so many stories… People in their own element do crazy shit.
15. I’m 27 and I’m working at a local rental house that is affiliated with a popular truck rental company. This woman comes in and starts asking about prices for a truck. She ends up coming in 3 times before her rental to get boxes and what-not. Each time she comes in I am the one to help her, and I’m no stranger to when someone is coming on to me. She is laying it on pretty thick.
She gets the largest truck in our fleet, and when I send her off I say something to the nature of, “Now you be careful. That’s a pretty big truck.” She fires back with, “Oh, No worries. I like ’em big.” I knew it was on.
While she’s gone me and the other guys are shooting the shit. I tell ’em how I can tell she wants it and all that other macho B.S. us guys always boast about. One of my coworkers starts razzing me about how old she was… He said late 40s, I said late 30s.
She’s 5’10”, Deep red Hair, Nice complexion (Freckles), and a fit body from what I can tell. She was wearing a fleece fall jacket and tight jeans. I would have been able to guess her age damn near spot on if it weren’t for that jacket.
My friends and I use a system called “The Tellbow.” You can get a good read on how old a woman is by how worn out her elbow skin is. It’s just like rings on a tree. Test it out.
Anyway, she brings the truck back and told me she swiped one of those barriers at the gas station. I go inspect it, rub some of the scuffs away and start checking in the truck… I’m sitting behind the wheel with the door open and my legs facing out the door. She comes up and puts her hand on my thigh and starts asking about the damage. Pins and needles shoot up and down my back… I say no worries, we’ll just forget it happened.
We go inside and she demands my number. This cougar was in heat. We go out, get back to her place. Wine, cheese, strawberries… put on a little David Grey and that deal was stamped. Cougs love David Grey.
When I met her I thought she was 37. Turns out she was 47. It’s mysterious how the body and mind work. Her face was 37. Her body was 27… but that vagina… it was definitely 47.
Turns out she was a little bit clingy… I don’t think she understood that this was a one time kind of deal. She started sending me really long, in depth texts about how people can connect spiritually despite age and this and that. I had known this lady for a total of 10 hours… TOPS. and roughly four of those hours was a crude amalgamation of heavy breathing and saying reaaaaaaally dirty shit.
And that is my one through-work hook up.
16. Man, I was 19 in college delivering pizzas and I went to this girl’s house who was in her underwear. She invited me in the house, shut the door, Proceeded to flirt with me half-naked and I just stood there like a lump on a log because I was retarded. That girl wanted to get banged by the pizza guy and I just thanked her and told her I had to be on my way.