2 comments/ 45464 views/ 3 favorites Amy the MatchMaker By: Bogey3 I met Amy one summer when I was building a retaining wall for some neighbors. Hot, sweaty work in the middle of a California summer. One day, the lady of the house, Mrs. Wilson, thought that I looked like I needed a little refreshment. A sweet, matronly lady. Little did I know that she thought of herself as a matchmaker. She sent her nanny, Amy, down the hill to ask what I would like. I looked up to see this very pretty and shy freckle-faced redhead. Actually I noticed all of that later... my first impressions were of a shapely young thing in short blue shorts and a white cotton blouse... pretty legs and a chest to die for. "Can I get you something to drink?" I could hardly respond, tongue-tied as I was. I think I said something lame like sure, whatever is handy. Wow. This cute little thing was talking to me! She brought some lemonade and we learned the usual. Do you go to college? Where do you live? Brothers and Sisters? Over the next few days, I drank a lot of lemonade and talked to her every chance that I got. On Friday, I worked up the courage to ask Mrs. Wilson if she thought it would be all right if I asked Amy to go to the movies. She said that it couldn't hurt to ask. And, she said she would put in a good word for me with her mother. We went out the next night to a movie... got along great. We began to go out every Saturday night and by the third date I had worked up the courage to kiss her. I had only made out with two girls before but it was clear to me she had never kissed anyone. After fumbling around a bit, she became a very enthusiastic learner. Every date after that included a hot make-out session and naturally progressed, although slowly. The first time I cupped one of those wonderful breasts, she took my hand off. But not the next time. After a couple of weeks of trying, I was able to unbutton her blouse, eventually baring those D size boobies... seeing, feeling and suckling those pretty (and rock hard) pink nipples became the high-lite of my young life. We eventually explored every thing that we could think of short of intercourse. This left us both flushed and excited by the end of every date. The question became: when would we lose our virginity? Wait until marriage, still years away? What to do... One night I showed her condoms that my friend Donnie had bought "in case we can't control ourselves sometime." "How do they work?" "I unroll one over Wilber (guess who he was/is) and he traps all of the sperm so you won't get pregnant." "Would Wilber mind if I put one on him now?" I thought that I had died and gone to heaven... thinking my chances of losing my virginity were very slim that night. It was a tight fit, but we managed. After that night, we fucked like bunnies, 3+ times a night and dating three or more times a week. Anywhere we could. Mostly in the car, but often outdoors in the woods, her mother's garage, her room, my room. We were caught a few times... by kids in the woods, once by a cop (who watched who knows how long time before he rapped on the window... taking in an eyeful of this naked lusty girl fucking her brains out... we think a while, because we never heard him until after I had cum and pulled out, leaving her exposed to his flashlight on her open pussy), once by some walkers and the spookiest time was in a deserted park, in the fog on a picnic table: just before I came, she said "Stop!" in a frightened voice... a hiker was about 50 yards away, jerking off... we left... and laughed about it later... she liked the effect that she obviously had on him. After two years of this, we eloped. She had just started the Pill so no more condoms!! Hooray! Sex was so much better without the rubbers. Our first night together we hardly slept. We were like kids in a candy store. We later figured that we had fucked 12 or more times in those 12 hours. Although that was a fun pace, our marriage settled into 10-12 times a week... once at bedtime on work days and more on the weekends. Life seemed perfect. So perfect that she wanted her best friend Judy to find someone as good for her as Amy thought I was for her. So now Amy was to become the matchmaker that Mrs. Wilson had been for us. Judy was shy like Amy, also a redhead but with much lighter and longer hair. Other than that, she was an opposite to Amy: where Amy was 5-3, Judy was 5-10, Amy was well rounded (34D-25-35) and Judy was very thin... she referred to her breasts as "two Bee-Stings" ( she was right... I got a chance to see them in a hot tub once... just two swellings with perfect raspberries for nipples). So who to find for her? Amy focused on tall guys, but we found some fault or another with each one. This game of ours went on for months... who to find for Judy. It was fun and kind of erotic. One night during pillow talk, I suggested my friend Donnie. Amy really liked him and loved the way he flirted with her... but... Donnie was 5-4 and she didn't think that they would be comfortable together. We talked about the possibility often, generally while we were in bed with me saying how erotic it would be for Judy's long legs to be wrapped around his skinny ass. Amy would pretend to be shocked that I was visualizing our friends fucking... and then join in the fun by suggesting positions that would work for them. We eventually invited both of them over for a barbecue and they hit it off wonderfully, as we had hoped, Amy's first success as a matchmaker! We began to include them in our social life as they were clearly a couple. Often when out together, people would think that I was with Judy and Amy with Donnie, given the relative heights... we quit correcting them and had a lot of fun with that, usually ending the evening with teasing about whom was going home with whom. However, we always got it right: short goes with tall. Probably the most memorable time of this was a weekend away at her mother's vacation home. We had a wonderful time wine tasting, eating, swimming in the lake and just generally kicking back. Both nights that we were there ended up in the hot tub... the second night we all were in our swimming suits when Judy says "wouldn't it be more fun to skinny dip?". I froze, fearing Amy's reaction. Imagine my surprise when she said: "Why not? But the guys have to shed their suits first." We all just sat their looking at each other for a couple of minutes when Donnie stands up and says: "Hell Yes!"while pulling off his shorts, so I too stood up and shed mine. We were both about half hard. I couldn't help but notice how thin and short he was. The girls just started giggling and Judy said to Amy: "I told you that they would fall for it. Men are so easy." Amy finally controlled her giggling to say: "Well, since they are such good sports, maybe we should too?" Judy: "Only if they turn their backs." So we did. When we turned back around, their suits were on the side of the hot tub and they were back under water. I, of course, was trying to see Judy's body and Donnie was staring at Amy... he had the better deal because Amy's big boobs were floating whereas Judy's were just blurry under the water. Seeing Donnie stare at her floating boobs made me hard as hell. We sat in there giggling, drinking wine and generally having a great time. After a while, Amy slides over to me and grabs Wilber. "What is this?" she grins. She then straddles me and I slid right in. Judy gasps and says "Are you guys doing what I think you are doing?" Amy: "Well, we are married aren't we?" At that point, Donnie stood up and went over to Judy. I couldn't help but stare at his stiff dick. The shaft was skinner and shorter than mine, but the head was swollen much bigger than the shaft. I had never seen anything like it. Judy bent over the side of the tub and presented her backside to him and he entered her. We had never seen anyone else fuck before. Amy got off of me and turned around so she could fuck me and watch the action. I was so damned turned on that I had to hold perfectly still inside of her so as not to cum instantly. We sat there open mouthed and watched them. After some long slow strokes, he pulled almost out and began popping that swollen head in and out. Judy began moaning loader and loader, saying "yes, just like that, right there, don't stop!" as he quickened the pace. When it became clear that he was close to cumming, Amy bore down on my dick with her pulsating pussy so that Donnie and I came at almost the same time (he won by a couple of seconds). This was more exciting then being caught in public. Later we were all a little embarrassed to talk about what we had done, but we did start planning the next trip up to the cabin. We had no idea it could be so hot to watch other people fuck or that they said a lot of the same things we did... lol. At this time, Donnie was in the Army, based nearby. Before we could plan that next weekend, Donnie got orders to ship out to Korea. Their relationship became one by mail. She also moved out of the area for a new job, so our only contact was occasional letters and phone calls. After a few months, Amy began to sense that Judy might be involved with someone else and, sure enough, he had swept her off her feet. The bombshell was a letter saying that they had run up to Reno and gotten married. We were shocked. Soon we got a letter from Donnie that he had gotten a Dear John letter... and he was obviously broken up. We exchanged consoling letters for a few months until one arrived that said he was returning to the States in time for Christmas. We wrote back and insisted that he come over for dinner the Saturday after Christmas. Now, Amy the matchmaker decided that she really had to get into action. She felt that she had failed Donnie with Judy and set out to find the perfect match for him. She was consumed by this for weeks prior to his arrival home. She got out her old year books looking for candidates and took over most dinner conversations with possibilities. One or the other of us rejected most of them but she did get it down to a short list. Donnie arrived that Saturday afternoon bearing gifts of wine and fruit. He gave Amy a big hug and said how nice it was to get away from the family for the evening and just have a good time. We started on the wine and had him tell us all about his adventures in Korea. All through this he flirted openly with Amy, telling her how much he missed her smile, how sexy she looked in her clothes, among other things (wink). I caught him several times looking at her cleavage... she was wearing a thin white blouse that she had unbuttoned enough to be interesting without quite revealing her bra. Her nipples were hard enough to stand out... hmm. She must like the attention. The more wine we drank, the bolder he got, and she was loving it. It was clear that he had not had female companionship since shipping out and was looking forward to meeting some new girls here at home. That was the perfect opening for Amy to chat him up on her list of possibilities. Throughout the dinner, she told him about one after another. Some of them he knew and rejected outright, others he didn't and was politely interested. This banter continued after dinner when she finally asked him : "What DO you want in a woman?" He gallantly responded with: "One just like you. You don't have a twin sister, do you?." She blushed: "Be serious, what would work for you?" "You are just the right height... for dancing and other fun things." Brighter red now: "O.K., we are looking for someone my height" "And you curve in all the right places" Laughing: "So you like big boobs?" (My shy wife would never have said that sober.) "Just yours... I still dream about that time in the hot tub. Speaking of which, someone with your passion" She turned even redder with that and said "YOU are BAD. You know, finding someone for you is hard" He was quick with his response: "It has got to be HARD to be good" After a very long, awkward pause "So you said that you like to dance? We hardly ever do," looking pointedly at me. "Nothing that I enjoy more, in fact"... looking over at me... "mind if I ask Amy to dance?" "Be my guest. Take her for a test drive! You can see if the height and curves are as good for dancing as you think" She blushed again and said to Donnie "Thank-you, you are such a gentleman," stuck her tongue out at me and got up holding her hand out to him. So I put on some soft music and they began to dance. At first, they were a little stiff, not getting to close to each other, but after a few minutes she stuck her tongue out at me yet again and relaxed, snuggling up closer to him. Watching them so close to each other was a huge turn on for me and I was disappointed when the music ended. "Should I play another song?" "Better not, I might forget that this lovely lady is your wife." She came back and sat down next to me. She was clearly flushed and breathing heavily... damn, that turned her on. And her nipples were really standing out now... wow. I love to see her turned on. He said nice things about what a great dancer she was and how nice it was to hold a woman in his arms again. Now if she could find someone who danced that nicely and maybe a great kisser too that would be nice. They continued to chat about the perfect date for him... who sounded more and more like Amy. After some time, she announced that it was time for dessert, and we all drifted into the kitchen. Donnie leaned against the doorway and I pointed out to Amy that he was under the mistletoe. Maybe if she kissed him, she could figure out what kind of a kisser he wanted? I have no idea what that meant, but they both liked the idea. She went over to him and gave him a peck... I laughed and told her she would never learn anything from that, she needed to really lay one on him. Now she turned all red all over again and said: "If you insist!" and with a very mischievous grin went over and draped herself around him, giving him a long, deep and passionate kiss. "Is that what you had in mind Love?" "Wow" Donnie: "That is exactly what I want" laughing. Amy then broke away, and like nothing had happened, said that we were out of whipping cream for the dessert and would you guys mind going out and getting some? Donnie immediately volunteered to go, but I said no, I knew where the store was, I would go. He went to put his coat on so I said: "No need for both of us to go out in the cold. Besides, you and Amy still have not figured out who the perfect match is. You stay. I'll go. Just don't do anything that I wouldn't." I said with a wink and a grin. Donnie responded with: "I'll just stand here under the mistletoe until you get back" And to Amy, I said: "Now don't be taking advantage of this poor lonely guy in his tipsy condition." me. Amy just stood there blushing and and then with a wicked grin said ... "Brat! Take your time we have a lot to discuss." I was gone maybe 20 to 30 minutes. Thinking how fun it was to tease Donnie with leaving them alone as I approached the steps to the front door. I glanced in the window to the living room and froze. At first I wasn't sure that I was seeing what I thought that I was seeing... Amy and Donnie were sitting on the coach... MAKING OUT! I got very flushed and started breathing hard... maybe I will just stand here for a while and watch. As the scene began to become clear to me, I could see that she was holding his face in her hands, kissing it all over. He had one arm around her... and... ... one hand was cupping her breast. My legs became weak and my dick began to stir... unbelievable. After a while, he began to pinch her nipple and she tilted her head back in ecstasy, I could almost hear her moan through the window. He began to nibble her ear as he slid his hand from her breast, down her side to her knee. As he slid his hand between her knees, she pulled back and took his hand from her legs and put it back on her breast... interesting message. Second base OK, not ready for third base. I watched them smooch some more, waiting to see if they would progress again, but eventually she broke it off. Just in time for me ... the cold was getting to me. I was not sure that I wanted them to know that I had been a Peeping Tom, so I made a lot of noise unlocking and opening the front door. As I entered, Amy was at the door while Donnie remained on the coach (I figured he couldn't stand without embarrassing himself). She looked ravishing. Hair disheveled, blouse not quite tucked in, one less button done (revealing edges of her black bra) and very flush with excitement. But, she was cool, like nothing had happened. She lead me into the kitchen, taking the whipping cream and setting out to complete the dessert. "So what did you guys do while I was gone?" "Oh, we just chatted about this and that. Still haven't figured out the perfect match for him." "Really. From looking through the window, I thought that you had and were celebrating." I said with a big grin. Long pause, Amy turning many shades of red. "Oh my God ... are you angry?" "No, should I be?" "I hope not. You know, just one thing lead to another." Laughing "One thing. And what was that thing? " "As soon as you left, I started back here to the kitchen. As I brushed past Donnie in the doorway, he took my hand and looked up at the mistletoe... so naturally I had to kiss him again." "He is such a good kisser that I didn't want it to stop... and I was thinking that you didn't mind us kissing, after all it was your idea that I kiss him, so why not enjoy it." "Well, I guess it was my idea. How did you get to the couch?" "Between the wine and the kissing I had to sit down, so he suggested the couch. When we sat down, he looked at me and said THAT was the best Christmas present he could ask for... so, I said that I enjoyed it too." "The next thing you know, we started necking again. It seemed so natural, but all we did was kiss and hug. I am glad that you are not mad." "I see he unbuttoned the top button." "Actually not, I did that went I went to the bathroom. I wanted to see his reaction." "You are so wicked... that turns me on." I said. "I did see you stop him at the knees... that was interesting... why did you draw the line there?" "Oh shit, how long were you out there? You must have seen his hands on my tits. Never mind, don't tell me... I decided that I had to draw the line somewhere short of sex... are you really not mad?" "Not at all, and more than a little turned on... Was he hard? Did you want to have sex with him?" "Of course he was hard" laughing. " Did I want to have sex with him? ... ummmm ... well ... I have never been so excited in my life with anyone besides you, so on some level, yes. But, we are married, so I tried to maintain some level of control." "You're not going to tell him what you saw, are you? I would die of embarrassment." "If I said that it was ok with me if you took him to bed, would you like to do that?" With a big grin: "Maybe" ... laughing ... "No! ... that would be so much fun, but we can't do that, can we? You are SO bad." "Baby, you are so turned on, I would love to see you finish what you have started. Shall I tell him the good news?" "Of course I want to, but don't you dare! .. let's just have dessert" So we went back in the living room with the dessert tray. I put it down on the table in front of Donnie and sat in the only chair in the room, leaving Amy to sit next to Donnie. She sat really close to him. I winked at her and smiled, rising my eyebrows as if to ask the big question. She smiled nervously shaking her head no, no, no ... a long pause, and than blushingly giving me a little nod yes. I looked at Donnie and said: "You have your choice of two desserts tonight, either or both. There is the high calorie delicious dessert on the tray in front of you...or... the no calorie luscious dish .... sitting next to you." Amy the MatchMaker "Which would you like?" Donnie looked a little shocked and laughed nervously saying": I don't think that I can very well have all of the one I really want, now can I?" He looked very guilty when I said: "Oh, I think you got a good taste of that while I was out. From what I could see, you throughly enjoyed it but did not get your fill... and I know Amy enjoyed it too" With that, Amy took his hand and stood up. He stood up with her. His hardness was obvious. She kissed him very passionately, pressing against him. When they broke off the kiss, they were both breathing deeply, oblivious to my presence. She took his hand again and led him across the room. When he saw that she was headed toward the bedroom, he looked back at me... and I gave him a wink and a nod. I followed, and as they went into our bedroom, she started to close the door. "Don't be shy. I'll just hang out here in the doorway" With that, she smiled nervously again, put both arms around his neck, began a deep kiss, pressing herself tightly to him, grinding her hips onto his stiffness. When they came up for air, he led her to the edge of the bed and sat down with her. They then took up necking where they had left off when I came home, his hands all over her and her hand under his shirt rubbing his chest and back. In no time, he had unbuttoned her blouse and was fumbling with the bra. She stopped him and stood up. She then shed her blouse and bra, giving me a big smile and mouthing "Oh My God." She looked so damn sexy, those fabulous boobs swaying as she went back to Donnie. She sat back down and his mouth went straight for those nipples... he suckled on one and then the other for the longest time. I was beginning to wonder if he would go any further when he finally put his hand between her knees. This time, she parted her legs willingly and pulled him a little closer, thrusting her pelvis toward his hand. My legs were so weak with excitement that I sat down in the chair at the foot of the bed and watched from there. After a bit of his suckling her nipples, she began to softly moan. After a good bit of this, she pulled back and stood up to remove her skirt and panties. He too stood up and quickly stripped... with his dick and it's bulb-like head springing out at full attention. While still standing, he took her naked body into his arms, kissing her and playing with one of her breasts. I could scarcely breathe, seeing them naked with each other. His hands then cupped her ass, pulling her against his hardness, her hands caressing his face as she kissed him over and over. After an eternity, she slowly backed to the bed, pulling him with her. As she sank to the mattress, she opened her legs and wrapped them around his skinny waist. He knelt in front of her, guiding his dick to her pussy. From my chair, I had a perfect view of Donnie's dick sliding into my wife. As he pressed it against her wet pussy, it meet a little resistance, but than popped into her, plunging all the way to the hilt... I thought that I would cum by just watching. "Oh Sweet Mother, Donnie, that feels sooooooo good. Just like that. Yes, yes, yes." Within just a few strokes, Donnie stiffened and said "Oh, No" as he started his spasm. You should have seen the horrified look on her face... such disappointment. She looked over at me and mouthed "Damn it!" I decided that I would take over and ripped my clothes off. I could not wait to get into her, having been turned on for most of the night. He rolled over to one side as I was undressing and saw that I intended to fuck her too. With that he got up and sat in the chair that I had been watching from. She opened her legs and arms to me. I slid right into her warm pussy and found it amazingly slippery from his cum... that excited me even more and I realized that I was not going to last any longer than he did so I held very still, not moving... but, I still came with the most intense climax ever... without ever taking a stroke! Those are the most intense. She starts giggling "Too much for you boys?" I slowly untangled myself from her and Donnie said "Nooooo ... Mind if I try that again?" He was already hard and good to go. "Get that back in me now!" she responded (this coming from my shy little wife). So I sat back in the spectator chair to enjoy the show. She opened up again to him, but this time he lasted a while. From my chair I was focused on his dick sliding in and out of her dripping pussy, his balls bottoming on her bottom ... very very intense to watch. Listening to her encouraging him on got me instantly hard. After lots of slow, controlled stroking, he pulled back, and started popping that head in and out of the entrance to her pussy. She just went wild... bucking up and down, moaning "Right there, Just like that, faster, yes, Yes, YESSSS!!!" I got even harder watching this, so that when he came again, I was very ready. As soon as he got up, she motioned me to get back on board. This time she was even wetter and slicker than before. I fucked her long and hard with the stiffest dick I had ever had and she just kept moaning softly "yes, oh yes, yes, yes." After I came this time, I was exhausted, so I rolled over to one side of her, kissing her and fondling a breast. Donnie lay down on the other side of her, hard again, and played with the other tit. She put her arms around both of our heads and pulled our faces down to her tits, wanting us both to suckle her... and we did. After a bit of this, we both started stroking her inner thighs, still latched onto her boobs. We worked our way up to her pussy, first rubbing the sides and eventually both putting a couple of fingers in... this drove her nuts again. "I need a cock inside of me NOW. Whose turn is it?" So Donnie mounted her for the third time... and they had a long, slow fuck that ended nicely. "Hmmm that was nice... but I need to cum NOW, and it is your turn" looking at me with a wicked grin. So I got up to show Donnie the position that usually got her off. Given how turned on she had been for hours and how well fucked she had been for the last hour, I had no doubt that we could get her over the top. I got on my knees between her legs while she was on her back. We hooked her knees over my shoulders and I slipped my cock in at that extreme angle... this has my cock rubbing the inside front of her pussy. It didn't take long for her to start jerking and moaning and generally going wild... and that is guaranteed to make me cum with her, so I did. "That is the hottest thing I have ever seen, your pussy thrust up in the air like that, his dick going in and out and your boobs bouncing almost over the top of your shoulders," Donnie said. "Mind if I try?" "Oh god, not just yet. That is exhausting work and I have to recover. Want to try it doggie style?" she said as she licked her lips. I returned to the spectator chair (the box seat, so to speak) as they got into position. I was not disappointed. Watching him pull her hips onto his dick and seeing her boobs bouncing underneath of her was yet another pleasure. They had another long slow fuck. And then it was my turn again, and again, watching them fuck had made me way hard. She stayed on her knees so my fourth time in her was doggie style too. Instead of just watching this time, Donnie got on his knees next to the bed and began kissing her and playing with her boobs. When I came this time, she slowly rolled over while still locked to his lips. He got back on the bed, lying by her side without breaking lip contact. She reached down, tugging on his cock, so he rolled over on top of her, she spread her legs again and they began a really long slow fuck that must have lasted half an hour. When he got off this time, she threw her arms back, legs apart and said: "Wow, I don't know if I can take any more." Then she looked at my hard again dick and said with a wicked grin "Well, maybe one more time, if you are really good" So I fucked her for the fifth time, doing missionary again, like the first two times. After that we collapsed on either side of her and lazily played with her body, taking turns kissing her lips and her tits. After a long while, she said: "So, I finally wore you two out, he-he" Donnie: "If you wore us out, why am I hard again?" and he was. She told him to lay on his back for the sixth and final time that night. She then got on top of him and impaled herself on his cock. Rode him slowly for a long time until he came again. I initially watched from the chair, focused on her ass riding up and down on his cock ... and when she lowered her boobs to his mouth I moved onto the bed to watch him suckle her as she rode him. I then lay next to them so that when she dismounted him, she mounted me. Just unbelievably slick with cum and still a fabulous turn on ... maybe my best fuck of the night ... well, maybe not. LOL. My shy wife had just fucked 12 times in a few hours ... awesome. After we recovered a bit, he said he had better get dressed and head home. She won't hear of it, given how much wine we had and how exhausted he must be. She got up and made up the couch for him to sleep on... she was so pretty walking around naked while she got it ready, I wanted to fuck her again... But it was time for sleep. I slept like a log... exhausted. The sun streaming in the window woke me about 8a.m. to an empty bed... I could smell coffee so I knew she had been up for a while. As I got out of bed, I realized that I was hearing an unfamiliar, rhythmic sound, like mattress springs? I walked nude into the living room and was surprised to see her pretty white ass appearing and disappearing from the other side of the couch... the one that Donnie had slept on, and, the one that I had caught them necking on... somehow it seemed fitting that the adventure had started and ended on the same couch. I walked over and watched until they were done... he looked up, startled, and said "I hope we didn't get you up" But in fact they had gotten my cock up so I took her one last time as she bent over the coach as he sucked her nipples one last time. When Donnie had left, we talked a bit... it turns out that she got up to pee in the middle of the night and found him awake... so they did it again... this incredible gal had fucked us 15 times in maybe 10 hours... and it was the first time she had fucked anyone but me. I loved it. "So you still haven't found Donnie a match." "Darn, I'll just have to keep trying, won't I?" Amy the Match Maker said with her mischievous grin.