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Painting and Delivery Sexcapades

So many women, so little time

Swingers Heaven Logo 4
21 min
I'm a delivery driver with almost 6000 deliveries under my belt in 3 years. Out of that many deliveries, I've had a few sexual adventures, and multiple flashings by different women. Prior to that, I was a painting contractor for 30 years, with probably over 3000 jobs, with the same amount of sexual encounters. I could probably make two separate threads, but decided to combine them. I'll start with the painting stories. I had met a gentleman at his house on a Wednesday. We walked the house and he told me everything he wanted done. It was a very expensive house, decorated with a lot of music paraphernalia, so I assumed he had something to do with the music business. His taste in colors was eclectic, but that didn't matter to me. In the basement area he wanted the walls black and the trim white, which I thought strange since there wasn't much light down there. While walking through another part of the house, I could see out the sliding glass doors that he had a very large pool. I figured everything up and gave him the price. He agreed and asked me when I could get started. I told him it would be Monday before I had a crew free to begin his job. He said he had to fly to New York on Sunday and would be gone all week, but that his girlfriend would be here all week. He told me just to come in the house and get started, and that she would greet us when she got up. I got there with my crew on Monday as promised, at about 8:30 a.m. Since it was a large job, I brought 5 men to make sure the job was completed as quickly as possible. I know the homeowner said we could just go on in, but I was uncomfortable doing that since I knew someone was home. So, I knocked on the door, and no answer. I knocked again, figuring if she didn't answer, we'd go on in, but this time she answered. I couldn't believe my eyes as she opened the door wearing nothing but a skimpy nightgown, and she was drop-dead gorgeous! She looked to be about mid-twenties to 30. She was stunning! She was very groggy, and said, "Hi, come on in and do whatever it is you're going to do. I'm going back to bed for a little while." She walked away--oh so sexily--and the crew and I just looked at each other in disbelief. "Ok guys, get your tongues back in your mouths and get to work! And do NOT flirt with that professional!! I walked the house with them explaining all the nuances of the job, then left to go check on my other jobs. "I'll be back at the end of the day. Remember, be professional!" I couldn't stop thinking about what happened. I've never come across anyone so brazenly sexy and unconcerned that she was barely dressed in front of a bunch of workmen. I'm sure I was hard throughout the day fantasizing about this beautiful woman. After I visited the rest of my jobs, I went back to check on this job. The crew were just loading up their work van when I pulled up, but the crew leader came running up to me before I even got out of my truck. When I did exit, he excitedly told me, "JJ, you won't believe what this lady did to us today! She drove us absolutely crazy!" Thinking this was going to be another one of those picky, troublesome customers, I asked what she did. "She was parading around in a bikini and high heels all day! She even went out to the pool and kept bending over, knowing full well we were in the room where we could see her! She kept coming into the area we were working, asking us if we needed any water or anything. It wasn't us who did the flirting, it was her!" I thought he was exaggerating what was going on, when she came out the side door. "Oh, JJ, I'm glad your back. Can I show you a couple of things with the job?" Yeah, she was showing a couple of things alright! I knew then that the guys weren't telling stories! "Sure, I'll be right in. Let me get a briefing from my crew leader then I'll come in." She went back in the house and I asked the crew leader, "Really, all day like that?" He nodded affirmatively. "Ok, well, be back here no later than nine in the morning. And ignore her as best you can. We are on a deadline, and I don't need any lawsuits!" They left, and I went into the house to see what she needed. It's not unusual for customers to ask questions at the end of the day, so I didn't think much of it, other than I usually don't talk to customers in bikinis and high heels. She did have a legitimate concern about one area where they did some drywall repair. But then, her true intention came out... She walked up the stairs in front of me, her perfect ass swaying from side to side. At the top of the stairs was a large bonus room, with a pool table, a desk, and high ceilings. She pointed to the peak where the wall met the ceiling and asked me what that spot was. I couldn't really see it, so I told her I would get the ladder and climb up. Sure enough, there was a small spot that the roller missed. 'You have great eyesight!", I stated. I went and got a brush and touched it up, then asked, "You said there were a couple of things...what is the other?" She asked me if Mike (her boyfriend) asked me to paint the master bedroom. I told her that he did not specifically ask, but said that he would want some other stuff done in a few weeks. She then asked me if I could give her a price while I was there, that she wanted to get it done sooner rather than later. "Of course", I replied. I then followed her into the master bedroom, which was right off the bonus room. She sat on the edge of the bed, crossed her legs and said, "What do you think?" I wanted to say, "I think you have fantastic tits and a perfect ass and a beautiful smile!", but of course, I didn't. I asked her to give me a minute while I walked off the measurements of the room. She sat there wiggling her legs, leaned back on her elbows. I thought to myself, "How do you expect me to concentrate when you're sitting there so seductively!" I came up with a figure, but asked her what color she was thinking. She said she wanted a lighter color. The walls were presently purple, so I told her it would definitely take two coats, which would up the price a little. She gave me the sexiest smile, and asked if anything could be done to lessen the price. I looked away, as I felt she was luring me in like Kaa the snake in the Jungle Book. When I did, my eyes landed on the headboard behind her, and I noticed it was FULL of porn videos. Probably 20 or so. (They were VHS tapes, so that tells you how long ago this was!) She started trailing her fingers over her boobs, and again asked, "Well, what can I do to get the price down?" Heck, she didn't have to do anything for me to get the price down! I'd take a loss to be able to come back and watch this sexy vision of loveliness walk around in that bikini! I kept my composure--outwardly anyway--and told her since we were doing so much anyway, I would do it for the one-coat price. I wasn't biting. But she was intent on following through with her wiles. She got up off the bed, walked over to me, embraced me, pushing her massive tits into me, and said, "Oh, thank you!," then planted a big kiss right on my lips and grabbing my crotch at the same time! I jumped back and said, "What are you doing? What would Mike think of this!" She smiled and said, "Mike and I have an open relationship, and I told him that if I fancied you, I would make a move. So he already knows. Besides, he's probably fucking some little hottie as we speak!" I stammered, "Uh...I don't...I don't know." "I think you do know...your cock is hard." I was. How could I not be? She stripped her bikini off and laid in the bed, spread her legs, and began to finger herself. "Get your clothes off and get over here and fuck me. If you don't, I won't get any cock for a week, and I need it!" She wins. I was out of my clothes in seconds, and went straight for her pussy. She was already soaking wet, and I licked her eagerly, looking up and watching her play with her huge tits. I was throbbing at this point, and in just a minute my cock was penetrating her slippery, wet hole. She must have been horny all day waiting for this, as she let out a loud, screaming orgasm, which sent me into my own. I pulled out of her and shot my cum all over her tight stomach and massive melons. Did I say "she wins?" Let me change that. I win. She informed me that I needed to repeat that every day during the course of the job, and I did. Fast forward a year. A similar episode occurs. I had always heard stories from people about things like this happening, but never believed them. I'm a believer now. Nymphomania is real. There is also another condition called "Persistent Genital Arousal Disorder", where women NEED to orgasm constantly, sometimes dozens of times a day. While this may sound hot, women who suffer from this will tell you it's quite painful, and time consuming. I hope none of these women have that condition, and that it's simple nymphomania...they just love being with a man. These two stories from my contracting days are only the extreme ones. There have been multiple flirtations and flashings that could have led to more, but didn't. Being in the contracting business, you have to be a people person. I'm naturally that way, and my personality makes people feel at ease with me. I also have a witty sense of humor, and who doesn't like that? The next extreme example was Claudia. She was in her late 30's or early 40's. She wasn't the sexpot like the lady in the first encounter, but she was really cute. She had blonde hair, a "mom bod", but was very busty. Her smile and laugh were infectious, and I felt really attracted to her. I would talk to her everday about the job, and often our conversation would get to personal matters. On one such occasion, she told me that she had a pet that had passed away about a month before we started work. We were sitting at the kitchen table, and while she was talking she started crying. I told her I was very sorry for her loss, and that I understood as I remembered all the pets that I had lost. It really is emotional, and I fought back tears as I told her of my losses. When I stood up to go out and check on the guys, she stood up too and came and hugged me. "Thank you for sharing, JJ, and for listening so attentive to me. I needed to talk about it." She held on for a little longer than a normal hug, and I didn't mind. I genuinely felt her pain, but I also felt her firm breasts pressing into me. She still held on to me, but pulled her head back and looked at me. "If my ex-husband were as attentive as you, we might still be together", she lamented. I didn't know what to say, I just looked into her eyes. It was almost uncomfortable, staring at each other but not letting go. Then, out of the blue, she kissed me. It was a quick kiss. She then said, "I'm sorry...I don't know why I did that. I just felt...felt like I needed to. You've been so kind, and I guess I felt the need for some affection of some kind. It's been so long since I've been held." I assured her it was ok, and she held me tighter, then leaned in for another kiss. This time it was longer, and before I knew it, she had opened her mouth and the kiss became sensual. She was squeezing me very tight now, her hands going up and down my back and down to my butt, squeezing it. I didn't move. I couldn't. My erection became obvious, and, without moving her lips, she grabbed my bulge. "I'm very horny, JJ...will you take care of it?" "Yes", I whispered. She grabbed my hand and led me to the bedroom. She slowly undressed in front of me, and I did the same. She was beautiful. Like I said earlier, she had a mom bod, but she looked so sexy to me. Standing naked, her tits were amazing and she was shaved. Both undressed, I moved closer to her and we began kissing again, her stroking my firm erection and me feeling her whole body. I pushed her back, and she fell on the bed and opened her legs. I kissed my way up and started licking her freshly shaved wet pussy. She tasted good. I continued kissing my way up her mummy tummy, then sucked her big tits as I fingered her sweet mound. Not a word was spoken. I made it to her mouth, and the kissing was passionate and heartfelt. The head of my cock was barely touching her slick hole, and she pulled me in with her hands on my butt and her pelvis pushing up to meet me. Her pussy felt so warm and tight. We were now fucking hard, and right when I was about to cum, I pulled out intending on shooting it on her tummy and tits, but she said, "No, cum inside me...I can't get pregnant anymore", and with that I pushed my cock back inside her and started shooting my creamy pleasure into her. She bucked against me, having her own orgasm. She was very vocal, "Yes! Yes! Fuck me with that hard cock...fill me with your cum!" I emptied myself into her, and her own creamy orgasm covered my dick. We were both spent. "Thank you, JJ...I really, really needed that." "The pleasure was all mine, Claudia. It really was." The job lasted two more days. We never fucked again, but she always mouthed the words "Thank you" with a smile through the window. When she paid at the end of the job, she gave me another big kiss and a final "thank you." Now, to my current job... When I was in the contracting business, a lot of ladies were flirtatious, and dressed extremely sexy knowing there would be people in their house. No bra, open shirt, short shorts...just enough to tease, but not enough to be obvious that they wanted anything but to tease. I'm sure my men went home and wanked at the end of the day. Fast forward to now. I'm in the delivery business, and I find women are the same. They answer the door scantily clad with a sexy smile on their face, knowing that they turn men on. I'm sure it makes them feel sexy. I've seen my share of breasts, barely covered, when making deliveries. Some even bend over to pick up something to make sure I get a clear shot of their cleavage. But then there's the women who take it to the next level. In the three years I've been in this business, I've had three sexual encounters. Why, I don't know. I'm not as young as I was when I was contracting (which was 30 years ago), so I don't understand the attraction. Why me? I'm 61 years old, with a dad bod, and although my hair isn't all gray, my whiskers are. Why would a 20 something year old young lady come on to me? I don't get it. When I'm on my way to their house, they can see me picture on the app they use to order, and they know what I'm driving. My info is on there too, so they know how old I am. I don't get it. Don't get me wrong, I'm not complaining, but some of these women are HOT and could have any guy near their age that they choose. Oh well, be that as it my, I'll share a few stories of what happened. Some of the people I deliver to are repeat customers. We know each other by name and have a good rapport. Instead of just dropping off their order and leaving, we talk, ask about family, and even a little banter. I enjoy talking to them. The first lady I had an encounter with was in her early 50's. Yes, someone more my age! She was always dressed for business, and always looked very sharp. We chatted a lot back and forth over the months that I got to know her. I would turn my app off when I got to her house because I knew there would be at least 15 minutes of talk before I could leave. She liked to talk. I was on my way to her house and started thinking about her. She was very pretty, and had a nice body. She always showed a hint of cleavage, and always had full make up on. And she was single. I went to the door and knocked, and she answered with her usual smile. "Hi JJ, great to see you!" "Always a pleasure, Marie", I replied. She said she had just put on a pot of coffee, and would I like to join her for a cup. I followed her in the house and sat at the kitchen table, and before I knew it, 45 minutes had passed. We were really enjoying out chat. But then, she asked me a question out of the blue, totally off topic of our conversation. She undid two of the buttons on her blouse, showing more of her cleavage, and said, "JJ, are you attracted to me?" I was a little stunned, but I answered honestly. "Marie, I think you are incredibly attractive and very sexy. I imagine any one who knows you thinks the same." "Well, I'm very horny and I want to fuck you. Are you up for it?" Wow, that was forward and very blunt! But what was I going to do? My cock was already straining against my pants, and as she was saying those words she was removing her blouse. Wow, her tits were huge. Other than the cleavage, she hid them well! I told her yes, I was up for it. Figuratively and literally. Without saying another word, I walked over to her and pulled her in for a kiss. Her lips were soft, her boobs pressed firmly against me. We began to furiously undress each other, and by the time we got to the bedroom, we were fully naked. She looked incredible. Big, firm tits. A tight ass. Her pussy was shaved and I could see her glistening in the light. I moved my hand down to her pussy, feeling her wetness. Our kisses were deep and erotic. Her hand was on my rigid member, stroking me up and down. She pulled me into her, rubbing my cock up and down on her clit, getting my member wet with her juices. We then fell to the bed and in no time we were fucking fast and furious. I sucked her erect nipples while penetrating in and out of her sex. She pushed me off of her and made me lay on my back, then lowered herself onto my cock and rode me like a bucking bronco. I rubbed her big tits while rhythmically matching her bounced on my dick. I few minutes later she arched back and began screaming, "I'm cumming! Fuck, I'm cumming!" That was it for me...I began unloading my cum into her pussy, filling her until it ran out of her and onto my pubic region. We layed there for a few minutes, then cleaned up. "Thanks for the package", she quipped. I'm sure she wasn't referring to the box I had delivered earlier. There were other incidents, but this is the last one I'll write about for now. And this is the one that startled me the most. I walked up to the door for the last delivery of the day and knocked. This pretty young lady, late 20's I'd say, answered the door wearing nothing but white panties and a half t-shirt. She was not very busty, a b-cup I'd say, but her nipples were hard and poking through her shirt. She was cute as a bug's ear. I had heard of stories like this, where a pizza delivery guy would be greeted by a nude woman, but I thought it was just urban legend. Yet, although not totally naked, here it was right in front of me. "Well then, this is new..." I said, and handed her her package. "I want to suck your cock", she bluntly said. "Will you come in?" I looked around to see if I was on Candid Camera, or for anything else suspicious. I think I was kind of in shock She stepped back and motioned for me to come in. I did, and she shut the door behind me, removing what little clothing she had on and dropping to her knees. Man, was she really cute!! She had long blonde hair, a beautiful smile, small tits and a clean-shaven pussy. She wasted no time pulling my pants down and taking me into her mouth. I detected movement out of the corner of my eye, and looked to see what it was. About four feet away stood a young man, rubbing his crotch watching the whole thing. I immediately went in to defensive mode, pulling myself away from Ms. Cutie, clenching my fist ready to fight my way out of here. He put both his hands up as if to say "Stop", and said, "No, no, friend. It's okay. This has been a fantasy of ours...for her to suck off a stranger while I watch. She's my wife. We mean you no harm." "That's pretty risky, man!", I shot back. Why did you choose me? You don't know me. What if I was a psychopath?" "We know your company...we know they vet their drivers thoroughly, and thought this the safest way. Please, will you help us with this fantasy?" I looked down at his wife, and she was nodding in agreement. But, by now, I was no where near hard anymore. Nothing like the feeling of being robbed or worse to make you lose an erection! I said ok, and she immediately went back to work. In no time she had me hard again, and Ms. Cutie had some mad oral skills. She ran her tongue all up and down my shaft, licking, sucking, and stroking me. She was an eager cock sucker. I kept looking over at hubby to make sure he wasn't doing anything out of the ordinary. He wasn't much taller than me, maybe the exact same as me, and weighed about as much as me, but a lot younger. I checked him about 3 or 4 times, ready to go back into defense mode if I had to. But, the last time I looked over at him, he had his pants off, stroking his cock to the sight of his wife blowing me. His cock was massive! He then circled around behind his wife, being careful not to get near me, so as not to spook me. He knelt down behind her, and she lifted herself up so he could slide underneath her. I thought to myself, no way can this petite little cutie take that massive cock inside her, but take it she did. Without her mouth leaving my cock, she slowly worked her was down on to his monster member, then riding it hard while continued her greedy sucking. I watched hubby's eyes shut tight, then he moaned out his orgasm, filling her pussy with his cum. She too started moaning, bouncing on his dick furiously, which sent me too over the edge. I yelled out that I was cumming, but she didn't move, and I emptied my pleasure cream into her mouth. OMG, what a little hottie! We cleaned up, then they introduced themselves to me. We exchanged names, and they thanked me for helping fulfill their fantasy. I received a lot of $10 tips that day, but that by far was the best tip ever!

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