Helping out neglected milfs

When I was in my early teens I mowed lawns and other things to make spending money. But it turned out to have some amazing perks as well. We lived in a fairly upscale neighborhood but my parents wouldn’t just give me money. They wanted me to earn money to help me see the value of hard work. Several of our neighbors were so busy with work and other things that they didn’t have time to mow their lawn’s or do other things around the house. Which I’d learn went into their bedrooms as well. Several of these guys were on their second marriage and had much younger wive’s who I’d heard people in the neighborhood refer to as trophy wives. Which at 14- 15 yrs old I didn’t yet fully understand.

I was large for my age at over six feet tall and very muscular from playing several sports so they had no problem hiring me to do things around their house. But in due time I learned that their wive’s had some things for me to take care of their older husbands were neglecting to take care of at home. I noticed right away some of them didn’t want me to refer to them as Mrs so & so. But preferred I use their first name. The first one was only a couple of houses from where I lived, her name was Brenda. I’d always watched her whenever I’d see her out because she was not only very beautiful, but was smoking hot. Even though she dressed conservatively you could see she had an amazing body. Which to be honest I’d jerked off several times thinking about her.

From the first couple of times I mowed their lawn I noticed she’d come out and sunbath on the back patio. That’s when I got to see that my fantasies of what she’d look like under those outfits I was used to seeing her in didn’t do her justice. And it looked like each week I’d get to see more and more of her sexy body as she laid out in the sun. If I’d been older I might have wondered why she chose to lay out when the sound of a loud lawnmower was only feet away. But I was just enjoying the view. But each week her bikini’s got smaller & smaller. She’d lay on her stomach and the suit looked like one small thread that disapearred between her ass cheeks. And she’d untie her top, but would raise up to get lotion and rub it on her legs allowing me to see her big tits just hanging there in full view.

Usually when I was about half way finished she’d have me stop and insist on giving me a cold drink. Her tits would be on the verge of falling out while she stood there in front of me, and she’d always tell me it would be cooler if I’d take my shirt off. After I did she always complimented my body. When I was finished for the day she’d insist I come inside for another cold drink and she’d take her time paying me, always wanting to chat. And I noticed she seemed to be curious as to if I had a girlfriend and things like that. And always saying she bet I had girls chasing after me because I was so handsome and had such a great body. She’d also comment quite often about how her husband was gone so much and when he was home he was so tired. In a round about way telling me she was lonely and that he wasn’t taking care of her in bed. But saying it was only because he worked so hard and because he was so much older than her.After a few weeks of this she started adding that she needed a strong young guy like me. But make it sound like she was just joking.

After about six weeks of this she’d come to lay out and ask if I’d be offended if she laid out nude saying she didn’t want tan lines, and adding that she’d feel safer with a strong man like me there so some stranger couldn’t bother her. And of course told me not to tell anyone saying others might not realize what good friends we were, then talk about the trust we’d built with each other, and say after all she’d never told anyone how her husband wasn’t pleasing her in bed and how bad she needed a strong guy to help her through that. All the time while rubbing my shoulder’s and my chest saying how strong I was and how lucky any girl would be to be with me. This soon started to include her saying what I needed was a woman with experience to show me what a girl likes. Then she’d go and stretch out on her lounge chair totally naked. Which it didn’t really register until much later that half the time she had a big umbrella over her blocking the sun. A couple of weeks of this and things heated up. When she had me come in to pay me she’d still be nude.

Then she finally moved things along on a faster pace. One day while she stood there naked she asked if I thought she had a nice body? I of course said I did and she asked if I liked her breast? But before I even answered she took my hand and placed it on one of them and had me start to squeeze it and rub her hard nipples. She told me how good that felt and asked if it was the first time I’d felt of a woman’s boobs? I lied and said yes not wanting to tell her my older sister had been letting me play with her’s and much more. She started to moan and tell me how much she missed the touch of a man. Soon she had me fondling both of her tits and then sucking on them. She moved one of my hands to her pussy and had me put a couple of fingers inside her. As she moaned and told me how good that was she said we could help each other. That she could show me what girls liked and I could show her the pleasure her husband never wanted to give her. In no time she pushed my shorts & underwear down and started stroking my hard cock.

She had me totally nude then she dropped down and started sucking my cock. I was so turned on I shot a huge load of cum in her mouth in no time. I told her I was sorry and she said no problem that she loved the taste of a mans cum. Then told me it being the first time a woman had sucked my cock she wouldn’t have expected me to last long. Again I couldn’t tell her my sister suck my cock all the time. She led me to the bedroom and had me hard again in no time and gave me a big boost in confidence when she said mine was the biggest cock she’d ever had and she couldn’t wait to feel it inside her. She had me lay back as she straddled me and slid my thick 9″ cock inside her wet cunt. As she rode my cock she leaned forward and had those big tits in my face. She was moaning harder than my sister ever had. And though I didn’t want her to know I’d been fucking my sister I wanted to give her a really good fuck.

I rolled her over and put her legs over my shoulders and started pounding my cock as deep and as hard as I could. Her loud moans were turning into screams as I fucked her for all I was worth. She had at least 3 orgasms before I dumped a load of cum inside her. She was spent but I was still wanting more. I started sucking on her tits again as I told her she’d just fulfilled a fantasy of mine and told her how I’d often masturbated as I fantasized about her. I told her she was the sexiest woman I’d ever seen in real life and looked better than most of the girls I’d seen in magazines. She looked like she was going to cry and I asked what was wrong and she said it had been forever since her husband had complimented her. She said how sweet I was and that I was the best lover she’d ever had. In no time we were fucking again, this time I took her from behind and she asked how I knew all these positions and I lied and said I’d seen them in magazines. This time when I was about to cum she had me shoot off in her mouth again. It was getting late in the day so I helped her change the sheets on the bed and left.

After that I was fucking her every week after mowing the grass, for some reason it turned her on more if I was hot and sweaty. But it seemed like funny timing when another of the trophy wive’s whose yard I mowed was at home on those days. Before she’d always gone to the country club because she didn’t like the noise from the mower. I’d always come back at night and her husband would pay me. In fact I’m not sure if she’d ever really seen me. But suddenly she was at home every week and like Brenda she started paying a lot of attention to me. Her backyard was wide open to the other yards where Brenda’s had privacy so Linda didn’t come out much when I was there. But after the first week or so when I knocked on the back door to say I was finished unless there was something else. She called down from an upstairs window and told me to come in that she’d be right down. When she came in the room with a skimpy towel on exposing more than it was covering and saying she’d just got out of the shower I started to wonder. Because when I saw her in the upstairs window she’d had a blue terry cloth housecoat on. And her hair looked like she’d just left the salon.

She insisted I drink a soda and right away started talking about her husband never being home and when he was he never payed attention to her. And that it had been age’s since the last time he’d touched her. About then I wasn’t at all surprised when her towel fell off and she stood in front of me totally naked. And instead of putting it back on she just picked it up in a bunch and held it in her hand. She said there was no need in covering up I’d seen all there was to see. Then she started saying anyway I’d probably seen lots of women naked. And said they were probably all prettier and sexier than her. This lady could have been a pin up girl. She looked like a perfect 36-24-36 with blonde hair & blue eyes. Every inch of her looked perfect. As I told her she was one of the most beautiful women I’d ever seen she looked down at the bulge in my shorts and walked over to me and started rubbing it and said well it looked like I liked what I saw. I knew what was going on so I started playing with her big tits as she said I’d have to keep this our little secret as she led me to the bedroom.

She wasted no time and was on the bed and I know it wasn’t a coinsadent she put her legs over my shoulders like I’d done with Brenda our first time and almost every time since she enjoyed it so much. As I pounded my cock inside her she was telling me she wished she’d known what she’d been missing all those weeks she’d left when I came over. The whole time I was fucking her it was like I was fucking a model from a magazine and when I told her she got this sexy look and said that actually she had been in a couple of men’s magazines. That got me so turned on I almost fucked her into a coma. I’m not sure how many orgasms she had. But she was beaming when I finally shot off inside her. She got her breath and went down and started sucking my cock and as she did said her husband didn’t like oral sex he thought only whores would suck a guys dick. And said she loved loved sucking dick, and especially one as big as mine. That she got to show off her skills, then started taking my cock down her throat with my balls hitting her chin. I was rock hard again and this time to no surprise she had me fuck her from behind just like I’d fucked Brenda.

As I was about to cum I was thinking about her big tits and how much I’d like to fuck them and shoot my load on them like my sister had taught me to do. I rolled her onto her back and then straddled her. She got a huge grin when she saw what I was doing and pressed her tits together around my cock. As I fucked those big tits she told me I was full of surprises and said she loved having her tits fucked and taking a load of cum on them. But hadn’t done it in years, it didn’t take long until I shot off on those beautiful big tits. She lifted them licking off what she could and as she did told me that the next week she wanted me to start off fucking her tits and she wanted me to cover her tits and face. Then surprised me when she asked if any women had gotten me to fuck them in the ass? It was in a way like she thought I was fucking a lot of women. And not saying girls but women. The next week we wasted no time in heading to the bedroom as soon as I finished the yard and I coated her tits & face in cum. Then we took a shower together and I fucked her in the ass. As I was leaving she said she had a friend who could use my services. I said it was almost the end of grass cutting season and she smiled and said Carol would find something for me to do.

It turned out Carol was younger than the other 2 women who were in their mid-thirties. Carol was only in her late twenties. She was hotter than the other two had been. She was probably about a 34C-24-36 with long black hair and blue eyes. She was so sexy it was like being in a dream. And she didn’t play games. When she answered the door she was wearing a garter belt & stockings with matching bra & panties a pair of spiked heels and a white silk housecoat opened just enough to get a peek at what she had on. She introduced herself and leaned in and kissed me. I hadn’t mowed the lawn or done anything and she was leading me to the bedroom as she told me how much she’d been looking forward to this. She quickly undressed me and when she looked at my cock smiled and said they weren’t kidding. I said what and she said nothing that she was just very pleased. She had me get in bed as she stood at the foot of the bed and did a sexy striptease in front of a big mirror where I could see the back and the front. She left only the garter belt & stockings on, something I’ve loved ever since that day.

We kissed and I spent a long time sucking her tits and she sucked me off for a few minutes then asked if I knew how to eat pussy? I said I did and she had me get down beside the bed while she sat on the edge. I ate her pussy for a good while before she had an orgasm. Then we fucked in a few different positions including the one’s I’d done with Linda and Brenda. But a few more as well. She kept going back to sucking on my cock which seemed to be something she loved. I fucked her pussy, her ass, her tits and it was just wild. As time went on I asked if she was sure her husband wasn’t going to come home but she assured me we had lots of time. Not being in a rush made my time with her the most enjoyable of all three of the ladies. And her outfits with the garter belts & stocking were something I got my wife into wearing years later when I got married and get turned on even today. I knew she knew about Linda and that Linda had sent me there but I didn’t know if Brenda knew.

Brenda and her husband had been on vacation for three weeks, him taking her for arm candy only. But when they got back I’d been keeping the lawn mowed and when I went to collect Brenda almost dragged me to the bedroom and we fucked like crazy. While she’d been gone I’d been fucking Linda every week and Carol even more often. And she’d insisted on paying me saying it was so my parents would think I was doing work there. In fact she was paying more than the other 2 women combined. After fucking each other senseless for half the afternoon and Brenda telling me how awful her trip had been. Her husband insisted she go places with him while they were there but then ignored her while socializing with people he knew. Only showing any interest in her when he introduced her so the guys would see what a hot young wife he had. But our sex was some of the hottest we’d had that summer.

But it was informational as well when she said she’d talked to Linda when she got back and found out she’d told Carol about me and that I’d been going there a lot. Then confided in me that both her and Carol were and that she’d gone over there a couple of times and were in bed together when she heard something and Carol said it was nothing. But when she left the door to the room next to the bedroom was open and it had been closed when they went into the bedroom. She looked in the room and saw a big chair and that there was a big mirror you could see through into the bedroom. Carol finally confessed that sometimes her husband would sit in there and watch her with other women. She didn’t know if he watched her with guys and said I was the only guy she’d heard of her fucking and that Carol told Linda everything and Linda told her. I was supposed to go to Carols the next day and I was wondering if he was in there while I fucked his wife. But the possibility actually turned me on and I fucked her even harder wanting to put on a show if he was watching.

It was almost time to go back to school and I knew the end of the best time of my life fucking three hot women. But it ended with a bang when Carol asked if I’d ever been with 2 women at once. She said the next time I came another girl would be there also and assured me she was really hot. It turned out to be a very hot 18 yo who was going off to college. I’d seen her around town and always had been turned on by her. Carol and Dawn were both wearing garter belts & stockings and nothing else. It turned out it was Dawn’s first time there and though she was bi curious she didn’t have a lot of experience with women. But she obviously had lots of experience with guys. She sucked my cock like a pro and Carol had me shoot off on Dawn’s tits and then licked it off. Then they both sucked me off switching back & forth until my cock was like a piece of steel. While I fucked Dawn from behind she ate Carol’s pussy. And after shooting my load inside Dawn, Carol licked & sucked it out as she ate dawn. I was just watching and catching my breath. They used a few sex toys on each other and Carol fucked Dawn with a strap on. Dawn seemed to be acting like she was into anything Carol. But only acting as It seemed to be fake smiles. And she seemed to relax when she was with me it just the two of us.

Then Carol took out a camera and Dawn seemed uneasy but Carol told her straight out it was part of the deal. She took pictures of Dawn in sexy poses and in various outfits. Then had me take pictures of them together kissing & sucking each others tits and finally eating each others pussy. Then Carol took pictures of Dawn sucking my cock and me fucking her from behind. But only showing me from the waist down. But once I started fucking Dawn neither of us wanted to stop and for the first time of the day she had an orgasm. She rolled over and we started kissing and were both enjoying it and if felt differrent than with those other women. Dawn left first and I heard Carol talking about her signing something. When she came back I fucked Carol again and got her off but was kind of let down after Dawn. When I left she paid me even more than usual. As I went down the street I was surprised to see Dawn sitting there in her car. She asked me to get in. And drove to a park in silence.

Once there she started by saying she wasn’t a whore and I said I never thought that. It turned out she’d worked for Carol’s husbands business during the summer to get money for college and he’d heard her say to someone she might not have enough and would have to wait another year. He made her a proposal after hearing someone had seen her kissing a girl. He offered her the money she needed to go to college and one thousand more. If she’d have sex with his wife and let her take some pictures. She didn’t know anyone else would be there and when Carol said it was going to be a threesome with a guy she was afraid it would be Carol,s very old & creepy husband. She said my being there was what got her through it. And that she’d really enjoyed being with me. Then she asked what College I’d be going to figuring there was a deal worked out with me too. She couldn’t believe I was barely 15. Then it registered who I was because she had been a friend of my sisters years before. She said I had grown, then said she couldn’t believe she’d fucked a 15 yo. Then after a pause she said or that the best sex I ever had was with a 15 yo.

She said she’d hoped we’d be going to the same college or could at least hook up before she left. After a minute she asked if we hooked up would I promise not to tell a soul. And added she would trust me she wouldn’t get me to sign anything like they had. I of course promised and a few days later when her parents were gone went over and we fucked like crazy and both really felt good about it. We corresponded for a while until she got a boyfriend. But it was the hottest summer any teenage guy could have. And had a lot to do with my sex life as an adult doing lots of things I was introduced to back then.

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