Cannon
07-12-2009, 08:57 PM
I'm 26 now, but back before I went to college I had a pretty amazing summer with members of the opposite sex just a little bit older. To be completely honest, I am grateful for the "training" I got from them.
I had my own landscaping business during the spring and summer while in high school. It was nothing huge, but it kept me pretty busy and the pay was good. Anyway, I began working for a couple originally from Sweden my last summer. I rarely saw the husband because I did their work on the weekdays. Sonya (not her real name) was about 50 I'd say, and while not a stunner was definitely a looker in her younger years. More, however, she held herself with a lot of sexual poise and a "presence" I'd guess you'd say. I never real thought about her in that way, though.
We became pretty good friends over the weeks. It was pretty clear, even though her phone calls with her husband were not in English, that her marriage was not the best. She never talked about it specifically, but it was pretty clear that he was a bit of a dictator. I had let her know a bit more of my relationships, actually. I had just broken up with a girlfriend, and found myself not getting laid at all that summer (okay, I didn't mention all that :) ).
I'd do other odd jobs for Sonya besides the yard work, and on one afternoon she had me putting a lot of heavy boxes into storage shelves in her garage. As I was picking one of the boxes up, I noticed through one of the flaps that was torn that the box was full of Playboys. Now, I was 18, hadn't been laid in a month. The garage was private (it was an L shaped driveway), and the shelves where I was was behind Sonya's car. I was getting stiff in my board shorts just opening the box. Before I knew it, I pulled him out and started taking care of myself.
I figured if Sonya came out to offer me some iced tea or something I'd have time to tuck him in and close the box. But I didn't plan on Sonya being in the backyard, and walking into the garage behind me. There I was, very stiff rubbing in a bit of precum, when I saw her, about 8 feet away at this point, chuckling a bit under her breath, wagging her finger, smiling like a very happy school girl. She was on the phone, and when she stopped her chuckle to speak what sounded like some harsh Swedish I knew she was speaking to her husband. My heartbeat was in my ears, and I'm sure I was beet red (which is rare for me). I was trying to put my cock away (a bit difficult in that state), and as I was avoiding eye contact what happened next surprised me. She took my cock out, just as soon as I had put it in, sat down on the box of old Playboys, and started blowing me. Every now and again she'd hum a "uh-huh" into the phone, and even stop sucking me off to say a quick word into the phone. To this day, it's the best blow job I've ever experienced. I started mouthing to her that I was going to cum. She crossed her arms across her chest, slid her sleeves off her shoulders, and slowly pulled her top down. I came all over her very ample tits.
She switched to English on the phone, and told her husband she was "cooking something up and all sticky," she'd talk to him that night. And then we were inside and up in her bedroom. Sonya offered some porn if I'd like it. It wasn't in a sleazy way or at all what she wanted, but because I think she was concerned of being so much older. I told her I didn't need any, which made her stifle a very self-satisfied smile. The truth is I really learned that there can be something sexy about women besides just their looks, and Sonya had that (whatever that was) in spades. I came twice more on her tits that afternoon, and Sonya came several times. She clearly was a very sensual woman, and was in need of a man with enthusiasm. That was my first time with a "milf," and I'll never forget it. Afterwards, she showed me an old Playboy from Sweden, which she was in. She was stunning when she was younger. That wasn't the last time I had sex with Sonya, not by a long shot. (Inside joke, she loved to watch me orgasm.)
A few weeks later I had an appointment for another lawn to take care of. When I got there, it was a very attractive woman in her early forties. She showed me around the yard and explained all the things she wanted done this summer. She seemed a bit domineering, slightly high strung, obviously a very successful, "go getter" type, but I could hardly admit that because she looked rather hot. She was a real estate agent, and was dressed pretty nice to go show a house. Looking back on it, I noticed she kept biting her lip and inadvertently licking her lip from time to time, but I was too young I guess to notice it. She wasn't flirting at all. Then as we came to the end of her showing me everything, she seemed to get a bit nervous. She said that Sonya had recommended me and thought that I'd be a "good fit." She was wearing sunglasses, but I could still tell that her eyes had gone from looking at my chest and arms down to my cock, then back to my face. It was as obvious as it could be while still being subtle. I heard the heartbeat in my ears and remember saying "I'm not sure how this works." She said "why don't we go inside and hammer out the details." The hammering occurred on her kitchen island. Michelle (not her real name) had a very fine body, one of the finest I had slept with at that time. Very tall legs, and wore those nearly-thong underwear that was high on her hips, to make them more impressive. Flat tummy, firm tits. When I was done taking her from behind she rode me to the finish.
Like Sonya, I was now screwing Michelle every week (she was my Thursday), and one time when we had sex again on the kitchen island a delivery guy got an eyeful. Looking back on it, I really learned how to get out one's stress with a good fuck from Michelle. That's the way she seemed to roll.
To make a long story short, this "word of mouth" kept happening. One was Meg (I'm giving her that fictitious name because she reminded me uncannily of Meg Ryan in You've Got Mail), 37, divorced with children. I didn't even realize for about a month that Meg wanted to get together. She seemed slightly nervous, wound up all the time, but her advances were so strange I didn't figure it out. One day I was working in the woods behind her house, when the sprinkler system turned on. I was pretty deep in the woods, but they would turn, and I ended getting soaked. I was already filthy before I got wet. As I walked across the lawn to go shut it off, I got more drenched. When I got there to turn it off, Meg was all apologetic and insisted I have a shower. I used a shower on her lower floor, stripped off and got in. A minute or two later Meg came in and put a towel on the rack. It was those beveled glass deal, so you couldn't make much out, but I could see clearly that Meg was hesitating to leave. When she did, she left the door open some, made some overstated excuse about doing it to let the steam out, then lingered outside the door. She must not have realized I could see her vaguely. I started putting on a show. I asked Meg why didn't she come join me. I saw the color of her shirt disappear from where the door was cracked, but then thinking better of it she came in the shower. Our first time was standing up. Unbelievably hot! It turns out she knew Michelle.
Meg was really a sweet woman, a little fragile after a divorce two years earlier. A graphic designer (which is what I studied in college), we had some pretty good conversations and she exposed me to a lot of artwork I hadn't known.
This isn't to say I still didn't have a lot of yard work to do. It's not like I was getting paid for sex. It's just that I worked that much faster so that there was a bit of free time before kids or a husband (or in Michelle's case, no one) came around.
Charlotte (not her real name) was French by birth. And while there is nothing sexier than a woman repeating "oui" over and over again in the bedroom, Charlotte was a bit inhibited. She was mid-forties, had never settled down, and was clearly trying to open up her wild side, at Sonya's suggestion. After confronting Sonya about the referral to Michelle, she realized I wasn't unhappy about it in the slightest and slyly said she wanted me to give a friend of hers a call. Charlotte was a librarian, an avid collector of books including erotica, and considered herself a writer. The first time I called on her she was poetically telling me she didn't have much of a garden, and what she had she kept well trimmed. She was incredibly buxom, just slightly overweight, but had the most incredible large tits. These were an incredible sight in a corset, or in a demi-cup bra, but I'm getting ahead of myself.
I hope all of this doesn't sound like bragging, but there was one more that I was seeing on a regular basis. Cara (yes, fictitious name) was asian, half Japanese actually, and thirty two. She was new to the area, moved with her work (and bought a house from Michelle). Michelle had referred her to me for yard work and had said nothing about sex, thinking Cara was happily married. But one day while working without a t-shirt, Cara came onto me very hard. I wish I could say I have morals but I didn't hesitate. The truth is that Cara was incredible petite and liked it very rough. I did her from behind and could feel her hip bones almost bruising me. She clearly wanted to get out some fantasies, having me pull her hair etc. At one point she went and got some handcuffs hidden away in an old suitcase and had me handcuff her. She wanted me to leave her like that for when her husband got home. I had to tell her that he might realize something was up, because you couldn't handcuff both of your hands to bedposts without a little help. (Go figure how that would've ended up...)
Needless to say, I was getting laid at least four or five times a week. And once or twice that summer I hooked up with a girl my age at a party, but I couldn't help noticing the difference. Younger women were far too concerned with being what you wanted them to be, and trying to make sure they were doing a good job. Older women were into it purely for self satisfaction, and were too into themselves to care, and that was what made it so hot.
It never really went beyond the yard work "plus" with any of these women, except on two occasions. Sonya introduced me to a lot of cool things after we had sex. Like Marlene Dietrich, for one. Anyway, one night we went out to a burlesque show downtown in the city, dressed up very old school. I was in a suit from the forties. I had a fake ID, and with her by my side, it wasn't that hard to get in. We sat in this nice round booth, and Sonya kept a nice hand on my growing joint throughout the show. It was nice and sensual, tasteful, fun. We had a lot of fun. She blew me in the car as I drove home.
The other exception was Michelle. She booty called me from an incredible piece of property with a secluded pool in the backyard. It was my first time having sex in the outdoors (unless you count the blowjob from Sonya in her garage). I hope there's a lot of chlorine in that pool.
So...summer was coming to an end. A few weeks before, I could feel that something was brewing among all these aforementioned women. Sonya mentioned that I needed to keep my Wednesday schedule at her place in a few weeks, as she and a few of the girls were planning a simple send-off for me. Nothing special, maybe some wine and cheese, sit out on the deck type of thing. When I got there, all the women I've just described were there. All looking extremely nice. Make-up. Nice summer outfits, very flattering. We were actually all in Sonya's very spacious living room ("great room" she called it). I had a beer, the women were drinking wine. It was very relaxed and nice. All of a sudden everyone started laughing and I asked what was up. It turns out the song had come on for one of them. Let me explain. There was a cd changer playing random songs from cd's and they had created a mixed cd with a song that each of them was going to strip to. The first song to come on (about half an hour after I had got there) was Michelle's. Michelle was gorgeous to begin with, but the lingerie she had on underneath was stunning. I was stiff very quickly. She sat in my lap, topless, with only some thigh high stockings a garter and some panties on, gave me a kiss on my forehead.
Everything seemed to be going in fast forward. The ladies seemed to have been sport drinking during Michelle's dance. I'm not that much of a drinker, and couldn't afford to really get wasted that day. I did however have some weed on me. I asked Sonya if she minded if I smoked. She said she didn't know I smoked, and then was mildly surprised when she realized what I meant. Sonya, Michelle and Cara helped me finish it. I lit another. Cara started getting paranoid and ended up leaving almost immediately. If I'm honest, I can't say I was too concerned. Michelle was sitting right next to me and said at one point, "Are you ready for your going away present?" I said, "I thought I just had it." She didn't say anything but lead me down the hall to a guest bedroom. There were speakers in the room, but we could hear the women down the hall trying to be nonchalant. I was pretty high. We went at it. I just remember how loud the headboard was against the wall. While I found Michelle very hot and erotic, it made me appreciate Sonya's liberalness all the more. I was pretty sure she was the one who had orchestrated it all.
Looking back on it now that I'm a little older and wiser, the women must have spent a lot of money on that day. The make-up was perfect, new dresses I bet and definitely very expensive lingerie. Even the cheese and the champagne must have cost a lot. They must have worked on that day for weeks, but made it out like everything was spontaneous. When Michelle and I came back in the room (Michelle had instructed me to take a shower, and then we returned, both of us naked), they all clapped.
Anyway, I watched an incredible striptease and got it up for each one that afternoon. Every time it was new bedsheets (silk was a new experience), sometimes candles, sometimes rose petals etc. Each woman clearly had set up their fantasy. When a song came on, suddenly it was time for a striptease, and one of the other ladies must have gone and set up the room. Luckily for me, the songs weren't coming back to back. :)
Needless to say, I have some incredible memories of that afternoon. Charlotte in a brimming corset...Meg in all white...Sonya in fishnets...Michelle in red and black...
So, this is not to brag but to say from the bottom of my heart thank all of you older women who show us young men the ropes. The end of that day the other women had gone home and Michelle was instructing me, by example, on how to go down on Sonya properly (my first threesome). To say the least, you've made me a better lover.
I had my own landscaping business during the spring and summer while in high school. It was nothing huge, but it kept me pretty busy and the pay was good. Anyway, I began working for a couple originally from Sweden my last summer. I rarely saw the husband because I did their work on the weekdays. Sonya (not her real name) was about 50 I'd say, and while not a stunner was definitely a looker in her younger years. More, however, she held herself with a lot of sexual poise and a "presence" I'd guess you'd say. I never real thought about her in that way, though.
We became pretty good friends over the weeks. It was pretty clear, even though her phone calls with her husband were not in English, that her marriage was not the best. She never talked about it specifically, but it was pretty clear that he was a bit of a dictator. I had let her know a bit more of my relationships, actually. I had just broken up with a girlfriend, and found myself not getting laid at all that summer (okay, I didn't mention all that :) ).
I'd do other odd jobs for Sonya besides the yard work, and on one afternoon she had me putting a lot of heavy boxes into storage shelves in her garage. As I was picking one of the boxes up, I noticed through one of the flaps that was torn that the box was full of Playboys. Now, I was 18, hadn't been laid in a month. The garage was private (it was an L shaped driveway), and the shelves where I was was behind Sonya's car. I was getting stiff in my board shorts just opening the box. Before I knew it, I pulled him out and started taking care of myself.
I figured if Sonya came out to offer me some iced tea or something I'd have time to tuck him in and close the box. But I didn't plan on Sonya being in the backyard, and walking into the garage behind me. There I was, very stiff rubbing in a bit of precum, when I saw her, about 8 feet away at this point, chuckling a bit under her breath, wagging her finger, smiling like a very happy school girl. She was on the phone, and when she stopped her chuckle to speak what sounded like some harsh Swedish I knew she was speaking to her husband. My heartbeat was in my ears, and I'm sure I was beet red (which is rare for me). I was trying to put my cock away (a bit difficult in that state), and as I was avoiding eye contact what happened next surprised me. She took my cock out, just as soon as I had put it in, sat down on the box of old Playboys, and started blowing me. Every now and again she'd hum a "uh-huh" into the phone, and even stop sucking me off to say a quick word into the phone. To this day, it's the best blow job I've ever experienced. I started mouthing to her that I was going to cum. She crossed her arms across her chest, slid her sleeves off her shoulders, and slowly pulled her top down. I came all over her very ample tits.
She switched to English on the phone, and told her husband she was "cooking something up and all sticky," she'd talk to him that night. And then we were inside and up in her bedroom. Sonya offered some porn if I'd like it. It wasn't in a sleazy way or at all what she wanted, but because I think she was concerned of being so much older. I told her I didn't need any, which made her stifle a very self-satisfied smile. The truth is I really learned that there can be something sexy about women besides just their looks, and Sonya had that (whatever that was) in spades. I came twice more on her tits that afternoon, and Sonya came several times. She clearly was a very sensual woman, and was in need of a man with enthusiasm. That was my first time with a "milf," and I'll never forget it. Afterwards, she showed me an old Playboy from Sweden, which she was in. She was stunning when she was younger. That wasn't the last time I had sex with Sonya, not by a long shot. (Inside joke, she loved to watch me orgasm.)
A few weeks later I had an appointment for another lawn to take care of. When I got there, it was a very attractive woman in her early forties. She showed me around the yard and explained all the things she wanted done this summer. She seemed a bit domineering, slightly high strung, obviously a very successful, "go getter" type, but I could hardly admit that because she looked rather hot. She was a real estate agent, and was dressed pretty nice to go show a house. Looking back on it, I noticed she kept biting her lip and inadvertently licking her lip from time to time, but I was too young I guess to notice it. She wasn't flirting at all. Then as we came to the end of her showing me everything, she seemed to get a bit nervous. She said that Sonya had recommended me and thought that I'd be a "good fit." She was wearing sunglasses, but I could still tell that her eyes had gone from looking at my chest and arms down to my cock, then back to my face. It was as obvious as it could be while still being subtle. I heard the heartbeat in my ears and remember saying "I'm not sure how this works." She said "why don't we go inside and hammer out the details." The hammering occurred on her kitchen island. Michelle (not her real name) had a very fine body, one of the finest I had slept with at that time. Very tall legs, and wore those nearly-thong underwear that was high on her hips, to make them more impressive. Flat tummy, firm tits. When I was done taking her from behind she rode me to the finish.
Like Sonya, I was now screwing Michelle every week (she was my Thursday), and one time when we had sex again on the kitchen island a delivery guy got an eyeful. Looking back on it, I really learned how to get out one's stress with a good fuck from Michelle. That's the way she seemed to roll.
To make a long story short, this "word of mouth" kept happening. One was Meg (I'm giving her that fictitious name because she reminded me uncannily of Meg Ryan in You've Got Mail), 37, divorced with children. I didn't even realize for about a month that Meg wanted to get together. She seemed slightly nervous, wound up all the time, but her advances were so strange I didn't figure it out. One day I was working in the woods behind her house, when the sprinkler system turned on. I was pretty deep in the woods, but they would turn, and I ended getting soaked. I was already filthy before I got wet. As I walked across the lawn to go shut it off, I got more drenched. When I got there to turn it off, Meg was all apologetic and insisted I have a shower. I used a shower on her lower floor, stripped off and got in. A minute or two later Meg came in and put a towel on the rack. It was those beveled glass deal, so you couldn't make much out, but I could see clearly that Meg was hesitating to leave. When she did, she left the door open some, made some overstated excuse about doing it to let the steam out, then lingered outside the door. She must not have realized I could see her vaguely. I started putting on a show. I asked Meg why didn't she come join me. I saw the color of her shirt disappear from where the door was cracked, but then thinking better of it she came in the shower. Our first time was standing up. Unbelievably hot! It turns out she knew Michelle.
Meg was really a sweet woman, a little fragile after a divorce two years earlier. A graphic designer (which is what I studied in college), we had some pretty good conversations and she exposed me to a lot of artwork I hadn't known.
This isn't to say I still didn't have a lot of yard work to do. It's not like I was getting paid for sex. It's just that I worked that much faster so that there was a bit of free time before kids or a husband (or in Michelle's case, no one) came around.
Charlotte (not her real name) was French by birth. And while there is nothing sexier than a woman repeating "oui" over and over again in the bedroom, Charlotte was a bit inhibited. She was mid-forties, had never settled down, and was clearly trying to open up her wild side, at Sonya's suggestion. After confronting Sonya about the referral to Michelle, she realized I wasn't unhappy about it in the slightest and slyly said she wanted me to give a friend of hers a call. Charlotte was a librarian, an avid collector of books including erotica, and considered herself a writer. The first time I called on her she was poetically telling me she didn't have much of a garden, and what she had she kept well trimmed. She was incredibly buxom, just slightly overweight, but had the most incredible large tits. These were an incredible sight in a corset, or in a demi-cup bra, but I'm getting ahead of myself.
I hope all of this doesn't sound like bragging, but there was one more that I was seeing on a regular basis. Cara (yes, fictitious name) was asian, half Japanese actually, and thirty two. She was new to the area, moved with her work (and bought a house from Michelle). Michelle had referred her to me for yard work and had said nothing about sex, thinking Cara was happily married. But one day while working without a t-shirt, Cara came onto me very hard. I wish I could say I have morals but I didn't hesitate. The truth is that Cara was incredible petite and liked it very rough. I did her from behind and could feel her hip bones almost bruising me. She clearly wanted to get out some fantasies, having me pull her hair etc. At one point she went and got some handcuffs hidden away in an old suitcase and had me handcuff her. She wanted me to leave her like that for when her husband got home. I had to tell her that he might realize something was up, because you couldn't handcuff both of your hands to bedposts without a little help. (Go figure how that would've ended up...)
Needless to say, I was getting laid at least four or five times a week. And once or twice that summer I hooked up with a girl my age at a party, but I couldn't help noticing the difference. Younger women were far too concerned with being what you wanted them to be, and trying to make sure they were doing a good job. Older women were into it purely for self satisfaction, and were too into themselves to care, and that was what made it so hot.
It never really went beyond the yard work "plus" with any of these women, except on two occasions. Sonya introduced me to a lot of cool things after we had sex. Like Marlene Dietrich, for one. Anyway, one night we went out to a burlesque show downtown in the city, dressed up very old school. I was in a suit from the forties. I had a fake ID, and with her by my side, it wasn't that hard to get in. We sat in this nice round booth, and Sonya kept a nice hand on my growing joint throughout the show. It was nice and sensual, tasteful, fun. We had a lot of fun. She blew me in the car as I drove home.
The other exception was Michelle. She booty called me from an incredible piece of property with a secluded pool in the backyard. It was my first time having sex in the outdoors (unless you count the blowjob from Sonya in her garage). I hope there's a lot of chlorine in that pool.
So...summer was coming to an end. A few weeks before, I could feel that something was brewing among all these aforementioned women. Sonya mentioned that I needed to keep my Wednesday schedule at her place in a few weeks, as she and a few of the girls were planning a simple send-off for me. Nothing special, maybe some wine and cheese, sit out on the deck type of thing. When I got there, all the women I've just described were there. All looking extremely nice. Make-up. Nice summer outfits, very flattering. We were actually all in Sonya's very spacious living room ("great room" she called it). I had a beer, the women were drinking wine. It was very relaxed and nice. All of a sudden everyone started laughing and I asked what was up. It turns out the song had come on for one of them. Let me explain. There was a cd changer playing random songs from cd's and they had created a mixed cd with a song that each of them was going to strip to. The first song to come on (about half an hour after I had got there) was Michelle's. Michelle was gorgeous to begin with, but the lingerie she had on underneath was stunning. I was stiff very quickly. She sat in my lap, topless, with only some thigh high stockings a garter and some panties on, gave me a kiss on my forehead.
Everything seemed to be going in fast forward. The ladies seemed to have been sport drinking during Michelle's dance. I'm not that much of a drinker, and couldn't afford to really get wasted that day. I did however have some weed on me. I asked Sonya if she minded if I smoked. She said she didn't know I smoked, and then was mildly surprised when she realized what I meant. Sonya, Michelle and Cara helped me finish it. I lit another. Cara started getting paranoid and ended up leaving almost immediately. If I'm honest, I can't say I was too concerned. Michelle was sitting right next to me and said at one point, "Are you ready for your going away present?" I said, "I thought I just had it." She didn't say anything but lead me down the hall to a guest bedroom. There were speakers in the room, but we could hear the women down the hall trying to be nonchalant. I was pretty high. We went at it. I just remember how loud the headboard was against the wall. While I found Michelle very hot and erotic, it made me appreciate Sonya's liberalness all the more. I was pretty sure she was the one who had orchestrated it all.
Looking back on it now that I'm a little older and wiser, the women must have spent a lot of money on that day. The make-up was perfect, new dresses I bet and definitely very expensive lingerie. Even the cheese and the champagne must have cost a lot. They must have worked on that day for weeks, but made it out like everything was spontaneous. When Michelle and I came back in the room (Michelle had instructed me to take a shower, and then we returned, both of us naked), they all clapped.
Anyway, I watched an incredible striptease and got it up for each one that afternoon. Every time it was new bedsheets (silk was a new experience), sometimes candles, sometimes rose petals etc. Each woman clearly had set up their fantasy. When a song came on, suddenly it was time for a striptease, and one of the other ladies must have gone and set up the room. Luckily for me, the songs weren't coming back to back. :)
Needless to say, I have some incredible memories of that afternoon. Charlotte in a brimming corset...Meg in all white...Sonya in fishnets...Michelle in red and black...
So, this is not to brag but to say from the bottom of my heart thank all of you older women who show us young men the ropes. The end of that day the other women had gone home and Michelle was instructing me, by example, on how to go down on Sonya properly (my first threesome). To say the least, you've made me a better lover.