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"
