Recently I was doing some home-improvement work for neighbors while they were on vacation.
I was almost done for the day when I saw a minivan pull in the driveway and the woman driver got out — the neighbors’ daughter, Stephanie.
That was convenient for me, because I’d done some work for Stephanie and her husband and they owed me a fair amount of money. I wanted to discuss her paying me what was owed.
Stephanie is a woman in her 30s, married with three kids, and has taken excellent care of herself. She has a great body, with nice tits and an ass a guy could get into. I’d have been up for enjoying that ass anytime, but knowing how conservative and smugly moralistic she is, I wouldn’t dare say anything out of line to her.
She was wearing a V-neck top that displayed a lot of cleavage. I had a hard time keeping from staring. When I brought up the money she and her husband owed me, she said they were having a hard time paying bills since she was laid off and only her husband was working. I told her it was okay and not to stress, but apparently she was stressing, since they owed quite a bit.
She felt bad and asked if there was anything at all she could do to alleviate some of the debt. She stroked my arm as she asked this. Was she suggesting something I wondered. I took a shot. “I know you’re a married woman with a family,” I said, “but I’d be willing to knock off at least $75 for a better view.” She looked down at her top to see what I meant, then looked back at me and asked me if I was serious.
Coming to my senses, I said she didn’t have to and I was sorry. We were both quiet awhile. When I turned to leave, Stephanie asked if I was serious about the $75. Cautiously, I said, “Maybe.” She looked around to see if there was anyone there, then asked if I would promise not to tell anyone, and I told her I wouldn’t.
She took another glance around, then undid a button on her top, exposing her left breast. I enjoyed the view of that balloon-like breast for a minute or two, and then she recovered it. She smiled broadly, then asked if there were any other offers.
I said, “Another $25 for a look at both.”
She hesitated, then said, “Okay, but not out here. Let’s go inside quickly.”
We went around back and down to the half-finished basement. In the basement she again warned me not to tell anyone around town, and again I promised.
She wanted me to know that, although she was very much attracted to me she was doing this because she felt terrible that she and her husband couldn’t pay me back quickly enough. She didn’t want me to think of her as a whore or something. I told her again she didn’t have to do it, but she said, with a wink, that she wanted to so she could ease her mind, and her urges. I couldn’t believe she felt that way about me!
She asked again how much I’d knock off for exposing both breasts. I said I’d take off $100 if she removed her entire top and bra. She pondered, then said, “Okay, but you can’t tell a soul.”
“My lips are sealed.”
Slowly, she undid her top and removed it, followed by one shoulder strap after the other of her bra. Then she unclasped the bra and let it fall to the floor. At first she covered her breasts with her hands. Then she dropped them, baring her big tits. Her nipples were quite stiff, and so was my cock!
I stared silently. Stephanie asked if I liked them, and I nodded. I said they were “absolutely beautiful.” I said I’d give her another $75 off if she would let me touch them. She said that for $100 I could touch all I wanted.
“Deal,” I said.
I held Stephanie’s breasts, squeezed them, fondled them, tweaked the nipples. She tilted her head back and let out a soft moan. I really wanted to suck and play with them more, but I didn’t want to press my luck, so I asked if she wanted to quit or to keep deducting from her debt.
In a shaky voice she asked what I had in mind. I suggested that we take it one step at a time and she could quit anytime she got too uncomfortable. She thought about it, then agreed to my plan, again insisting on secrecy. She added that as long as it wasn’t actual sex, she would be willing to go pretty far. I told her not to worry, and she asked what I wanted her to do next.
I told her I wanted her to keep stripping for me, and I wanted to see her pussy. “No,” she said flatly.
“Okay, fine,” I said. “No problem. At least I got to see your gorgeous breasts. It was worth the $200 you got taken off your bill.”
I started up the steps, but Stephanie called after me saying she would do it. So I sat on the couch and watched as she undid the dress pants she was wearing and slid them down over her ankles. Next she slid her panties slowly down her legs and stepped out of them. She stepped back and leaned against a table that was behind her.
I took in every inch of Stephanie’s beautiful body, which was only a foot or so away from me. I told her to sit on the table so I had a better view of her pussy, and then she smiled and said that she’d just taken another $150.
She sat on the edge of the table and parted her legs so that I could see her clean-shaved pussy. It looked pretty damn good for a woman who’d given birth to three kids. Knowing that I had to behave myself, I leaned in as close as I could and asked if I could touch it. She asked how much more I would take off, and I said $50.
Stephanie nodded without speaking. I reached over to touch her puffy lips and then rubbed slowly up and down. I noticed she was beginning to get wet. She tilted her head back once again and moaned. While rubbing her, I inserted the top of my index finger in her pussy. I didn’t try to stick it in farther; first I wanted to see how she’d react. When she didn’t do anything, I slid it in deeper. When I got my entire finger in, she let out a moan. I just kept sliding the finger in and out, and she moaned a bit louder and gripped the sides of the table.
I finger-fucked Stephanie till she was close to climax, then stopped. She opened her eyes and stared in wild-eyed wonder. I took another gamble and told her I’d take another $100 off if I could drop my pants and have her stroke my cock while I kept touching her. She looked at the floor for a while. Again I said she didn’t have to do it if she didn’t want, and when she didn’t answer, I thought we were done.
Then she looked up at me and asked if I would really take the $100 off, and I said, “Absolutely.” In a low voice she said, “Okay.” Soon my erect cock was inches from her hands, and I was so excited, I was afraid I would blow my load too soon. She reached down and took my cock with her soft hands, and I rubbed her pussy some more. When I reinserted my finger in her, she tilted her head back and let out a bigger moan.
As her pussy got wetter, it made loud squelching sounds, and I whispered that I’d take off $50 more if she’d rub the tip of my cock against her lips. Without any hesitation she began doing it! I leaned in and kissed her neck lightly, and she tilted her head back still farther. I kept up my gentle kisses, and she kept rubbing my cock, getting it wet with her pussy juices.
As I was kissing her, she took her hands off my cock to adjust her position on the table, since she’d begun to slide. As she did, the tip of my cock slipped in her! Not realizing it, she shimmied a bit more, and the whole of my crown disappeared, plus an inch worth of shaft. Seizing the moment, I lowered my hands to her waist and drew her to me and slid all the way in her.
Stephanie just stared me in the eye with her mouth slightly open. After some time, she said breathlessly that I shouldn’t be doing that, but when I asked if she wanted me to stop, she just kept on staring at me while I moved slowly in and out of her. It felt incredible to have my cock inside this hot but self-righteous woman right in her own basement, knowing how holier-than-thou she and her husband pretended to be in the community.
Suddenly I lost it and blew wave after wave of come in her. When she felt me coming inside her, she gasped, “Oh my,” but trailed off.
When I pulled out, as we fought to catch our breath she asked me what just happened and began to panic when she understood that someone other than her husband had just fucked her. I tried to talk to her to calm her down, and after a minute or two she listened to what I had to say.
After a while she began to come around, and even asked how she could maybe pay the rest of their bill off. My cock twitched, and I looked down at it — and so did she.
“Right now?” she asked. I smiled and spun her around and bent her over the table. She gasped when I entered her come-filled pussy and began to pound her. Since I’d come already, I knew I could last a long, long time.
Then I decided it was all or nothing, and pulled my cock out of her sloppy pussy and moved it up. She knew at once what I meant to do and cried out, “No, please!” She tried to move away, but I held her and said, “It’ll be okay. Just relax. I promise it’ll feel very good.”
“I can’t,” Stephanie said. “I’ve never let anyone do that before. It will hurt me.”
“Not if you relax,” I said. “If you do it right, you can actually enjoy it.”
She hung her head while she thought. Meanwhile, I had my hand on her hips, and the tip of my throbbing cock was just touching her anus. After a long pause, she nodded. With a green light from her, I began to push in. Her anal ring gave way grudgingly and my cockhead popped in. She gasped and moaned.
As I pushed in slowly, she sobbed, “Go slow, please. I’ve never done this.”
“Okay,” I promised. “Just relax.” I pushed in her an inch or so at a time until I was fully embedded in her tight ass. This was an even more incredible feeling than her pussy. As I slid slowly in and out of Stephanie, she hung her head and moaned.
The feeling was so overwhelming that I was soon ready to fill her ass with my come. Surprisingly, as I was shooting, she cried out and had an intense orgasm. I slumped over on top of her while she convulsed and gasped for breath.
When I finally got off of her, she remained draped over the table, moaning. Both her ass and pussy were full of my come, which began to trickle back out. I asked if she was okay, and she nodded. I pulled up my pants, and as I finished dressing told her to consider her debt paid in full. I said I would never mention it again, and her secret was safe with me.
She thanked me weakly, and since her legs seemed a bit weak, I helped her get cleaned up and dressed, then helped her to her van and said that if they had more work for me to give me a call. As if in a daze, she said they would.
Stephanie then leaned in very close and whispered, “I would’ve done it for nothing. That was an amazing session.” I was speechless but satisfied as well.
I haven’t heard from them, but I’m ready to go if they call. I think maybe Stephanie’s avoiding me.