Mar 18, 2023 // By:analsex // No Comment
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I was heading out to Wal Mart for some groceries one day at the end of March last year, when I saw my neighbor Sherri from across the road walking down her driveway to check her mailbox. She waved as I pulled to the end of my driveway.
“Hi, Sherri,” I called out through my open window. We were friendly, but not especially close. I’d often see her getting the mail, or when I’d be out in the yard and she’d be coming or going. She was in her mid 40’s with a son who was a senior in the local high school, and a daughter who was a sophomore there. Sometimes we’d meet when I was doing a lap around the neighborhood-about a mile-and she was walking her dog. It always seemed she was going the opposite direction. We chatted occasionally, but nothing serious. She gave a lot of attention to her son, who was a standout player on the baseball team. As with most athletics, it required a lot of parental involvement, though I rarely saw Doug, her husband, with their son. He had some kind of sales job, and travelled a lot, since he didn’t seem to be around much that I could see.
Sherri is attractive in a girl next door MILF kind of way, blonde curls cascading over her shoulders, nice tits, I guess about C cup, and shapely, full ass. I had occasionally thought of what a night with her would be like, but hadn’t figured out a way to approach her without it looking like what it was. Since she lived so close, it was a delicate situation, and I didn’t want to create any bad blood in the neighborhood.
“Hey!!” Sherri called out as I turned onto the street. I stopped as she walked toward me. “You’re not going to Wal Mart by any chance, are you??”
“I am, actually. Can I pick you up something??”
Sherri looked at me a moment. “Can I ride with you??”
Hmmm…this might be my opening. “Sure. Hop in.”
Sherri got in, explaining that her daughter needed some supplies for a project she was working on. “Everything’s an emergency,” she said apologetically. “She just called me from her friend’s house. They’re working together, but don’t have a way to the store. I’d go myself, but my car’s in the shop til Monday, and my son has his car.”
“Do we need to drop the stuff off there??”
“No, she can get it at home later. She has the things she needs, just doesn’t have the display board to paste it on. He can do that tonight at home.” Sherri looked at me a moment. “Crap, I don’t have my purse!! Is it too much trouble to go back??”
“Don’t worry about it. I can spot you the board. Just pay me back when you see me.”
Sherri looked relieved. “Thanks,” she said. “I’ll make it up to you.”
I reached over to the console, putting my hand on hers. “Not a problem. It’s only a display board. If you skip town tonight and I never see you again, I’m only out, what, $5??”
Sherri smiled. I thought I felt her fingers entwining with mine.
“So, how have you been?? For all the times I run into you, we rarely talk.”
“Good. The kids are all doing well, though I wish I could get my baseball star son to think ahead a little more. The college scouts are coming around, and if he could get a scholarship somewhere, it would be a real help. But he has baseball on the mind, and the season is getting into high gear.”
“Yeah, sports will take a lot of your attention. At least he’s doing something constructive.”
“True,” said Sherri, distantly.
“How’s Doug these days. I don’t see him much.” I had noticed that his pick up, which was in the driveway most nights, had not been there the last several weeks.
“Well, um,” Sherri looked out the window. “We’re not together.”
I pulled up to the stop sign at the end of our road where it goes into the state highway. I looked over at her. She tightened her grip on my fingers. “I’m sorry,” I said. “That’s never easy.”
Sherri looked at me and smiled. “I’m not!!” She got more serious. “Things hadn’t been going well for a few years. That’s why you saw me out walking the dog a lot.” I thought a moment. I had run into her a lot more in the past year or so.
I laughed at her reaction. “I get that. But still, you have a lot of time invested in each other, over 20 years.”
“Twenty three, married 19. It is a long time.” We rolled on toward Wal Mart, about 15 minutes away. Sherri leaned over, putting her head on my shoulder. I wasn’t quite sure what to make of this unusual move, but I let go of her hand, reached over and pulled her to me, kissing the top of her blonde head.
“Thanks for taking me. This is a big help.”
“We can drop this off to your daughter if you want. It might make her project move along a little quicker.”
“You don’t mind??”
“Nah. Can’t be that far, can it??”
“She’s just over the other side of town, but with traffic and all, it may take 20 minutes, and then still we have to get home.”
“It’s not a big deal. I wasn’t doing anything that important anyway. And I’m enjoying the unexpected company.”
Sherri smiled and looked up at me. “Thanks. You’re sweet.”
“I don’t know about that. I try to help people out.” Sherri let go of my hand, wrapping both arms around my right arm, hugging it. istanbul escort She stayed there for a few moments before sitting up. For someone who was not really close to me til, well, ever, she was getting awfully cozy awfully fast. I didn’t mind it, really, but it was unexpected.
We ran off the fifteen or so minutes to Wal Mart, which gave Sherri and I a chance to get to know each other better, sharing the basics of our lives. I gave her the five minute version of my life story, and she gave me hers. She related how she and Doug had started out with a lot of hopes and dreams, and somehow had gone astray in the last five or six years. It was a common tale, told the world over. I pulled into a spot in the Wal Mart lot as we finished up her story, sitting a few minutes as we talked about life lessons and such.
Sherri was going a mile a minute, so I just sat and listened, taking in the expressions on her face, but mostly looking at how her blonde hair framed her face, and the brightness in her blue eyes. Finally she stopped, looking at me looking at her. “What?? I’m sorry, I’m rambling on way too long,” she said apologetically.
“No, not at all. I’m guessing you have not had too many places to let this out, and I’m happy to listen.”
Sherri smiled. “You’re sweet. Still sweet.”
“Maybe,” I said smiling at her, still taken by how pretty she was. I reached over, pushing a strand of hair away from her face. “But you are too. And beautiful.” Our eyes met, and we leaned toward each other, meeting in a short, sweet kiss. We pulled away, our eyes still fixed on each other. I took Sherri’s hands in mine. “Look, um, I’m retired and have quite a bit of free time. If you want to come over and vent, or just talk about anything, if my garage door is open, which it is most of the time in the warm weather, feel free to drop in.”
Sherri smiled at me, then leaned over to kiss me again, a quick kiss on the lips. “Thanks. I may do that.”
“I’ll look forward to it. Don’t be shy. I really mean it. Come over if you need, or just want some company.” I squeezed her hands and we got out, heading into the store. I didn’t need many items, and would have a quick pass through the grocery section. Sherri headed for stationery and art supplies, and thought she might pick up a few things she needed for the house, if I didn’t mind spotting her for them. I told her not to worry, and I’d meet her farther back in the store.
I worked through my list quickly, and was back in the dairy aisle when I saw Sherri coming toward me from office supplies. She was wearing sweat pants and a t-shirt; as she walked toward me, it was quite obvious she was braless under it, as her tits were bouncing enthusiastically as she approached. She dropped her things in my cart. “All set,” she said, catching her breath. After watching her quick approach, so was I.
“Good deal. I have two more things, and we’ll get out of here.” I picked up my last items, though I was now paying more attention to Sherri than the rest of my grocery list, watching her bounce as we walked the length of the store to get to the checkouts. I paid for our things, Sherri unintentionally making quite a show of herself as she moved around while bagging at the self checkout, and headed to the car. I loaded the bags in the back, Sherri taking the cart back, and trotting back from the cart corral. My heart leapt as I watched her tits shake under her shirt. She got in, caught her breath, and kissed me on the cheek.
“Thanks for doing this. It’s a real help. I’ll pay you back when we get home.”
“No hurry. It’s only about $12. I’ll never notice it. Any time that’s convenient is fine.”
Sherri smiled. “That’s sweet of you. Maybe I’ll stop by later.”
I smiled at her. “I’d like that. Now-how do we get to your daughter’s friend’s house??”
Sherri gave me directions, and we were off. We got to the friend’s house about 15 minutes later. She came out and got the supplies with a perfunctory ‘hi’ to me, and a short chat with her mom. That done, we headed back to our neighborhood. As I reached the stop sign at the end of the street, Sherri turned to me and said, “Thank you. I really appreciate the effort you’ve gone to for me today.”
“No problem at all,” I said. “Bringing this to her will make her get the project done quicker, and she’ll be able to do it with her friends, which adds to the teamwork aspect of it. She may even get a better grade, which is a plus. Besides, I get to spend a little more time with you.” I smiled at Sherri. I was discovering that I really enjoyed her company, now that I had a chance for more of it.
Sherri leaned over to kiss me on the cheek. As she did, she went to put her hand on the console to steady herself, but it slid off and landed squarely on the crotch of my pants. Ever since seeing her in the store, I had been replaying the sight of her bouncing tits as she walked toward me, which had left me with a steady hard on. The exchange with her daughter just then had relaxed it a bit, but I was still closer to full mast than furled.
Sherri’s hand kadıköy escort lingered a moment, then she realized what it was she felt. “Oh!!” she said, sounding surprised. “Have you been like that the whole time??”
I smiled back at her. She still hadn’t moved her hand. “Just since I saw you walking toward me at Wal Mart, and it became obvious that you’re not wearing anything under that t-shirt.” I reached over to give her right breast a squeeze, figuring if she had her hand on my cock, turnabout allowed me a feel, too. She felt soft, and I felt her nipple stiffen to my touch.
Sherri smiled again and looked at me. “That feels good. It’s been a while since someone touched me like that. I miss it.” She rubbed my cock through my jeans. “Why don’t we help each other out??” she said, going for my zipper. I turned the corner, thinking we should get off the block in case her daughter decided she needed something and maybe saw us still sitting at the stop sign. Sherri had me out in no time, and was starting to give me what was promising to be a masterful hand job.
A hand job is a fairly straightforward process: expose erect penis, stroke til it shoots streams of white goo. Yet, some women barely manage to do the basics, while others really have a touch for it. Sherri was one of the latter. Her hands were soft, and she was able to stroke me with just the right pressure-not too hard, enough to cause the tension needed to really stimulate, and she knew when to ease up to keep me from overheating too quickly. We took a slightly longer route back, one that would keep us out of the main part of town, allowing Sherri to work on me without fear of being observed by other drivers or random pedestrians.
Sherri spent most of the 15 minute trip home bent over the console, stroking me gently, getting me close to eruption, then backing off. A few times she had to sit up-those damn consoles aren’t too pleasant on a girl’s ‘girls’-which took the pressure off me while giving her some relief. The first time she sat up, I pulled up her t-shirt, revealing the loveliness I had suspected she was hiding all along, a pair of roughly 36C tits that were full and round, with pink nipples that stood out appealingly, surrounded by slightly lighter areolae. I enjoyed the way they swayed with the motion of the car. I reached over to play with the left one as we drove, making Sherri giggle.
“I don’t think I’ve had someone do that in a car since high school,” she admitted.
“Hubby not much for playing in the car??”
“No, not really. Said it was too distracting.”
“I can see his point. I mean, if I had those out in the open while I was driving, it might take my attention from the road, too. On the other hand, I don’t have a problem staying in lane, even with those out,” I said, giving her a look, and reaching past the left tit to give the right one some attention. Sherri aided my quest by pulling her t-shirt over her head and setting it in her lap. We were in a rural area, and didn’t need to worry about someone seeing us. I played with both tits, tweaking the nipples, which made Sherri squirm.
Sherri resumed her attention to my cock, which was standing tall through my zipper. “Why don’t we let that out a little more?? After all, I have my tits completely out.”
“Fair enough,” I said, lifting my ass off the seat. Sherri pulled them down so the waist was about mid thigh, giving her complete access to my cock and balls. She reached over, now cupping my balls in her right hand, her left slowly stroking me. I noticed the faint white band where her wedding rings had been. She held my balls as we drove, adding to the wonderful tension that was building as she continued to stroke. Every so often, she’d get me to the brink, then pull back as my cock throbbed in her hand, come oozing from the head. She’d hold still as it rolled off the crown of my dick and down her fingers. Once I relaxed, she’d resume her stroking, using the edged come as lube. Once, after edging me, she sat up. I took the come sliding down my shaft and rubbed it into her nipples, making her giggle and squirm.
It didn’t take long before we were close to home. We slowed long enough for Sherri to get her shirt back on, and me to get my jeans pulled up, though I did not zip or button them. We pulled into my driveway, behind the RV outside the two car garage, preventing a view from the side street. Sherri pulled up her shirt, revealing her tits, and went back to stroking me. I gave her tits a good feel, making sure to pay attention to the nipples so they stood out and stiffened. Sherri moaned softly as the electricity ran through them.
Sherri didn’t slow down from my attention, and I was soon on the brink. She sensed it too, her eyes were fixed on my swelling cockhead. “Come for me, baby. Let me see your fat cockhead shoot hot, sticky come all over my fingers.” She slowed her manipulation, ending with a long, slow, upward stroke. A short burst of come erupted from my dick, dropping onto her fingers, which were holding the underside of my shaft. The first big spurt went up in the air, kağıthane escort landing on her wrist. She started to stroke, using the come from the short spurt to lube my shaft. Another long spurt shot up, also landing on her wrist. She stroked up so her index and middle fingers were over the head. Another pulse, then a thick spurt shot into her hand, forcing its way between her two fingers and down over her ring finger and pinky. She stroked down, her thumb covering the head of my dick, another shot of semen hitting it and spreading over the head and down the shaft, then one more big but less forceful wad that spread over the head and down onto Sherri’s hand. She stroked my now come covered cock as another three or four smaller shots of sperm spilled out, Sherri smearing them around the head with her thumb. As she stroked, noisily now that my come was smacking every time she ran her hand up and down my shaft, I felt her body shake, and she let out a whimper.
She looked up at me, her face having a look of a woman who has just come. I kissed her as she slowed her stroking, then stopped. She looked down at my cock. “Wow!!” I said softly. “That was the most awesome hand job I’ve ever had.”
Sherri smiled. “I think that’s the most awesome hand job I’ve ever given.” She pulled her hand off my cock, licking the sperm from her fingers. “I’ve always loved giving a good hand job, but doing that for you really got me off, and you playing with my tits really started me off pretty good. I don’t think I ever made a guy come that much. Watching and feeling you come, well,” she blushed and pushed her hair back, “made me come, too. That hasn’t happened in a long time.”
I kissed her. “I’m glad my reaction gave you such a thrill,” I said as she licked in between her fingers. “Your touch is magical. We’ll have to do this again.”
Sherri looked at me and smiled. “Yes, we will.” She looked around, pulling her shirt back down. She kissed me again. “I should get back to the house. My son will be back from baseball practice any time. “Thanks for everything today.”
I chuckled. “No, thank you!! Going to Wally World was never so much fun.” We kissed as she got out and went across the street. She picked up the mail, then walked up to her door. I watched her walk away from me, admiring her form, which looked good even in sweat pants, which almost no one looks good in. She blew me a kiss as she stood in the door. I blew one back, and she was gone.
Now that we were better acquainted, Sherri come over several days most weeks, mostly just to talk, though more often than not, there was some hand job time. It seemed Sherri liked to play with a hard cock, and got off watching me come. Sometimes we’d sit together on the sofa while she stroked me to orgasm, sometimes she’d sit while I stood in front of her, she jerking me til I came on her tits. I’d play with them while she played my cock, and often I could get her worked up enough that she’d have a powerful orgasm when I came on them, then rubbed my sperm into the soft skin and nipples.
One day not long after we started, I went to reach into her sweats while she was jerking me, but she held me off. “Not yet,” she said, kissing me. “I’m still a little unsettled by the divorce, I’m just not ready to let anyone have my pussy yet.” She kissed me again. “So sorry,” she said, apologetically.
“Don’t be,” I said, kissing her. “Take all the time you need. I know there are a lot of things going through your mind right now.” I wasn’t about to upset the apple cart when I had a good thing going.
“Thanks,” said Sherri, returning my kiss. “I was afraid you wouldn’t understand. Besides, this is still a lot of fun. I’ve always liked giving a hand job.”
“I can tell. You’re really good at it!!”
Sherri laughed. “When I was in high school, I’d go out on a date and jerk the guy off while we were driving to the movies or someplace. That was always the hottest, driving along with his cock out, knowing people could see us if they only looked over. Watching my date come while we were sitting at a light was intense. I got where I could hold him back til I wanted him to come. I became known as the hand job queen.”
“I can imagine!! Maybe we should go on more shopping trips,” I suggested. “I can tell you from the guy’s perspective, there’s nothing hotter than riding along while your girlfriend is giving you a hand job, or sucking you off.”
Sherri looked at me with an expression of lust. “Yeah,” she said, her eyes getting a distant look. “We should do that.” We started coordinating out shopping trips, which often turned into long drives in the farmland in our area. Sherri would wear jeans or sweats and a t-shirt or tank top with no bra most of the time; when we were away from town, she’d pull it off and ride topless, which I enjoyed. As the summer wore on and her tan deepened, the freckles on her tits became more obvious, which only increased her appeal. One cooler day she came over in a zip front sweatshirt. We got in the car and headed out. Once we were out of our development, she unzipped it down to her navel, revealing her braless tits. We had a good time in the store as she leaned down for items on lower shelves, giving me a glimpse of her full, swaying tits. It was a real tease, but Sherri paid off on the way home, edging me til I came in buckets just before we turned into our neighborhood. When I pulled into my driveway, she licked all the come she had just extracted from my pulsing cock off my belly.
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