My sister and I live on adjoining one-acre lots in a sparsely populated development way out in the country. Between our houses is an area with a picnic table, an old fashioned swing hanging from a huge oak tree, a couple of barbecue pits and off just a little way from the rest, a trampoline. All of our kids are young adults now so the trampoline seldom gets used for anything other than a place for a private conversation or a place to lay out and catch some sun. But one night last summer it became a place of unexpected pleasure for me.
Most of my family had come out to one of the local watering holes to listen to me and my band. It had been a great gig with a loud, appreciative crowd that danced all night and tipped well. I was in a great mood when we finally wrapped up and got everything loaded and when I got home I was pleased to see that my nephew and a gal he’d brought home from the club and my oldest niece and her best friend were still up and laying around on the trampoline talking and drinking. I grabbed a cold beer out of the ice chest sitting on the ground and jumped up and joined them.
I don’t drink when I perform so I had to do a little catching up and as I opened my third beer I began to realize that Sherry, my niece’s friend was royally pissed about something. This really wasn’t an unusual occurrence. Sherry had been a bit of a drama queen the whole time that I’d known her. She’s a sweet gal but just never seems to fully grasp the concept of happiness. She’s always having boy trouble or parent trouble or work trouble and quite frankly, we’ve all just learned how to tune her out when she’s ranting about some real or perceived problem.
Well, this evening’s problem revolved around what an asshole some boy was and how one night he was all lovey-dovey and wanting to hang out and make out and get into her britches and how the next night the same boy wouldn’t pay any attention to her and how she didn’t understand why boys treated her that way. I made some soothing comment or another and she quieted down for a while. At about the same time my niece Christy said that she had to get up early, told everyone goodnight and left.
When Christy left Sherry scooted over next to me and put her arm through mine and sort of snuggled up to me. Now, I may be in my fifties but having a pretty girl grab my arm and push a very nice, very firm twenty one year old breast under my arm is just as much fun now as it was when I was eighteen. She said, “You know what I want to do? I want to get real drunk.”
I said, “Well, all right. Do you want another beer?”
She answered, “No, what else is there?” I thought for a second and told her that I had a nearly full bottle of Parrot Bay Rum in the freezer but that I didn’t think I had any cokes to mix it with. She said, “No problem. We’ll just drink it right from the bottle.” Seemed like as good an idea as any I could come up with so I told her that I’d be right back and left to get the rum.
When I got back to the trampoline the girls were gone and it was just my nephew sitting there. He sorta chuckled and said, “You know why she’s pissed don’t you?” I didn’t and told him so. “I boned her last night and now she’s mad because I’m not with her tonight. I told her before we left for the club that we weren’t going to be together. She just wasn’t listening.”
My nephew is twenty-four, three years older than Sherry and they’ve all known each other since grade school. Sherry’s always had a big crush on Michael but I didn’t realize that they’d ever gone to bed together until then. It did explain her attitude that night. “Well,” I asked, “where’d the girls go?” He said that they had gone to go pee and get some blankets. This was an August night in South Texas so I wasn’t real sure why we’d need blankets but I learned a long time ago not to question why women do certain things.
When they got back and settled down Sherry and I started taking long pulls on the bottle and before long we both had a pretty good buzz runnin’. Michael and his lady were on the opposite side of the trampoline under their blanket and it was obvious that they were making out pretty heavily. I had been sitting cross-legged for quite a while and was starting to get uncomfortable so I unfolded, made a couple of old man noises and stretched out laying on my back and checking out the millions of stars that you can only see when you live out in the country away from the city lights.
Sherry stretched out beside me and our combined weight sort of pushed us together. It was very comfortable and nice having a young lady lying next to me and making contact from shoulder to foot. I put both hands behind my head and just as natural as you please Sherry laid her head up on my chest and snuggled even closer.
In a voice so low that I could barely understand her Sherry asked, “Why do guys treat me like they do? It’s like they don’t respect me at all and they just walk all over me and I get so tired of it.”
Her question really made me think. We have a saying in our family: “Don’t ask if you really don’t want to know.” If she really wanted to know I’d tell her but I’d have to choose my words carefully.
Sherry hadn’t had much of a family life while she was growing up. Her dad was a successful contractor with a real fondness for booze and coke. Her mother was a controlling little harpy with the same bad habits and a quick temper. I don’t think they ever did one single thing to make her feel good about herself. Quite often when she was in her mid-teens she would come home from school and find a note taped to the front door telling her that her folks had gone to Vegas for a few days and that they’d see her when they got back. Subsequently she spent a lot of time at my sister’s house and more or less became a real part of our family.
Sherry is a beautiful girl. She matured physically fairly young but never dressed to flaunt it. She was a gifted athlete in high school and played varsity volleyball from the time she was a Freshman. She’s tall, 5’10” or maybe a little better with dark green eyes and beautiful dark brown hair. She has broad shoulders for a woman and hips that my dad would have said were meant for having babies. I always suspected that her breasts were larger than they appeared. It always seemed to me that she wore bras that were a size too small to keep them from bouncing around.
Sherry was always in need of nurturing and would often sit in my lap for a quick hug or snuggle up beside me when we were all sitting around watching TV. None of this was ever taken out of context nor did anyone in the family ever think too much about it. People need physical contact and she sure wasn’t getting any at home. And she didn’t really single me out. She was affectionate with everyone. But the bottom line was that I knew she had a pretty low self esteem and my experience in life has taught me that many people like Sherry let men walk all over them because they don’t think they deserve any better.
So in a whisper I began talking to her. I asked her some questions that would lead us to the point where I could tell her that as soon as she started liking and respecting herself and demanding that the men in her life treat her with respect they would. I was only telling her things that her father should have told her years ago and I sincerely hoped that she would take some portion of what I was saying to heart and that maybe she’d make some changes that would help her find a little happiness.
Sherry was very still for a moment and then without saying anything she got off the trampoline and walked into my sister’s house and I thought that maybe I had been too honest and had really upset her. I sat up and took a good pull on the bottle and looked over where Michael and his gal were. As far as I could tell they had both fallen asleep. Then I lay back down and just let my mind drift for a while.
In a few minutes Sherry came back out and jumped up on the trampoline. She grabbed the bottle and took a shot and then grabbed the blanket and spread it over both of us and laid back down with her back to me. Her head was on my left arm and her butt was pressing against my hip. And then while I was waiting for her to say something she reached behind her, placed her hand on my right hip and tugged. It was pretty obvious that she wanted me to roll over into the classic spooning position so I did. She snuggled back into me and let out a contented sigh.
Believe me, I was fully enjoying having a young sexy gal in this position but I still wasn’t thinking of acting on the circumstances or taking advantage of her. I soon found out that the decision had already been made. In a move that was so natural that I didn’t even give it any thought my right hand ended up on her right hip. It took me a second to realize that she had changed from the tight fitting pair of blue jean shorts to a baggy pair of shorts made from sweat suit material.
It suddenly dawned on me that Sherry was crying. I could feel her shaking just a little and hear her quietly sniffling. I whispered words of comfort until I could tell that she had quieted down. When I asked her what was wrong she turned her head and whispered that she knew that I was right about what I had said and that she loved me for being so honest with her. She said that all she’d ever gotten from anyone else that she’d asked that of was that bullshit about, “You just haven’t found the right guy yet”. She said that she always knew that there was more to it than that but just didn’t know what it was.
Then she did the last thing in the world a man way past middle age would expect a pretty twenty one year old girl to do. She took my hand off of her hip and placed it directly on her left breast. I lay very still for a second, in a little bit of shock I suppose, until she pressed my hand harder and moved it around a bit which I took as an invitation.
Very slowly and gently I began to caress and explore. When she had gone into the house she not only changed shorts, she had also removed her bra and except for the thin cotton t-shirt there was nothing between her and me. I placed my hand on her rib cage just below the left one and slid it up until I was lifting and weighing it. I avoided the nipple and just marveled at the firm, heavy feel. I then moved my hand up to the area above her breast and moved it down smoothing the t-shirt as I went. I could feel that wonderful slope at the top and this time let my palm linger on her nipple as I made my way back down to the lower part and I could feel it harden slightly.
After repeating these motions a few times and getting a couple of quiet, appreciative moans from Sherry I zeroed in on the nipple. At first I just circled around it with my fingertip and felt the aureole begin to stiffen. Then I gently grasped the nipple itself between my thumb and forefinger and began to lightly tug and pinch it. I remember this silly feeling of pride coming over me when her nipple grew as hard as any I have ever played with.
By this time Sherry was beginning to squirm some and press her ass back into my crotch. Now, despite what some story writers will try to make you believe men my age do not automatically sprout monstrous diamond cutting blue veiners at the first thought of hot, steamy sex but I did have the beginnings of a respectable hard-on growing in my jeans and having her push back into me was extremely pleasurable. So I removed my hand from her breasts and grabbed her hip again and pulled her tight against me and ground my crotch into her ass for a minute or two.
As I slid my hand back up I ran it under her t-shirt and went for the other breast. The feeling of her bare skin on my palm and fingertips was absolutely electric. It was so soft and silky and ever so slightly damp from the heat and immensely satisfying to the touch. She evidently enjoyed the skin to skin feeling as well. This time she not only ground her ass into my crotch but also reached back and began rubbing my hip and ass with her right hand and pulling me into her with some pressure.
I won’t say that I never had any little fantasies about Sherry while she was growing up because I did. But in my wildest dreams I would have never imagined that I’d ever experience first hand just how passionate she was. When I started lightly pinching and pulling her right nipple her body stiffened and she drew in a deep breath and held it for a few seconds and then let it out, shuddering in what could have been a small orgasm. It was incredibly sexy and again I felt a sense of accomplishment.
At this point there was nothing I wanted more than to kiss and lick and suck her breasts. Her nipples were just begging for more attention but when I tried to turn her toward me so that I could get to them she said, “No, I don’t want them to see.” I had completely forgotten about my nephew and his lady. I was so lost in the sensations of exploring Sherry’s body that they had slipped completely from my mind and at this point I really wouldn’t have cared if they watched. But I also didn’t want to take the chance of her turning off and depriving me of the fun that I hoped would follow.
When I was a young man just beginning to explore the world of sex I always took things very, very slowly with a new girl. Partially because I didn’t really know what to do, partially because I truly loved exploring every square inch of newly discovered skin but mostly because I was afraid that at any moment I would do something to scare her off and she would say no. Those early instincts seem to have served me well over the years and I really hoped that the slow approach would serve me well this night.
There was no telling if I would ever have the opportunity to make love to a woman this young and pretty again in my lifetime so I was going to draw this night out as long as I could. Instead of going straight for what I really wanted I put my right hand on her hip and let it rest there for a moment. I then drew it down over her ass and reveled in the feeling. Her ass was soft and firm at the same time and I loved the way it felt when I cupped one cheek in my hand. From there I ran my hand down her leg to about mid-thy and slowly started back up. With just my fingertips I lightly caressed that wonderful crease where the upper thigh and buttocks meet. I pushed my hand under her shorts and felt nothing but skin. She was either wearing a thong or nothing at all.
Sherry’s legs were closed at this point but she wasn’t playing games with me. When I moved my hand around to the front she immediately lifted her right leg and moved it up and back over mine. This way she opened herself up completely to my touch and was able to pull me even closer. The shorts she had on had the drawstring on the outside so with one smooth tug I untied them and was able to slide my hand inside. As I began my exploration I discovered a couple of things. As I hoped, she didn’t have any underwear on and she kept her pussy extremely well trimmed.
I spent a little time just running the flat of my hand all around her mound and then down her leg a little way and then very lightly teasing that little hollow on the inside of the thigh with just two finger tips. Her skin was slightly damp and wonderful to touch. When I first let my fingers graze the lips of her pussy she let out a low moan and pulled me even tighter with her leg. When I ran my middle finger slowly from just above her asshole to her clit she shuddered and said, “Oh, Jesus.”
She was already getting wet and I couldn’t keep myself from getting some of her juice on my fingers and then pulling my hand out of her shorts and up to my nose. My God, she smelled absolutely delicious. She smelled fresh and womanly and a little bit like strawberries and I wanted so much to stick my head between her legs and show her what an old man had learned to do with his tongue over the years but knew that it was impossible with two other people there on the trampoline with us.
Instead I pushed her leg off of me and began working her shorts down. When I got them down to her knees she finished the job for me. While she was busy removing her shorts I started kissing and nibbling her neck and right ear. I don’t know why but that little hollow spot behind the earlobe is one of the sexiest places on a woman’s body to me and she evidently liked it too. As I tongued and lightly kissed that area she put her leg back up on mine. When I sucked her ear lobe into my mouth and then gently chewed on it she ground back against me with considerable force. When I slid my hand back under her T-shirt I found her nipples even harder than before. As I rubbed and pulled on her nipples she reached between us and started fumbling with my belt.
My parents raised me to always be a gentleman and since she was having some difficulty getting my jeans open I decided to help her. I unbuckled my belt, unzipped my jeans and lowered them to just below my knees along with my underwear. As my dick sprang free she latched onto it like she was drowning and I was her lifeline. She pulled so hard and fast that it actually hurt and so I grabbed her hand and whispered, “Take it easy Sweetie. We’ve got plenty of time.” She took a deep shuddering breath and I could feel her grip relax a little. When she started rubbing my pre-cum around my dick head the feeling was so intense that I actually thought that I was going to pee.
At this point I was beginning to have a difficult time controlling myself. I would have loved to get her up on her hands and knees and just fucked her as hard as I could. But I still wanted to savor every feeling, every touch and every response. Besides, I felt an obligation to show her that she hadn’t missed out on anything by not hooking up with my nephew. So I reached around and grabbed her chin, turning her face toward me so that I could kiss the corner of her mouth and just skim the soft inside of her lower lip with the tip of my tongue. She gently bit my tongue and then sucked it into her mouth for a toe curling French kiss literally had me gasping for breath.
“My God,” I whispered, “where did you learn to kiss like that?”
She softly laughed and said, “Seventeen magazine and a lot of practice. And you’d be surprised who I practiced with.”
“Hey, no fair teasing. Who?”, I asked.
“Can’t tell you,” she giggled, “I promised her I’d never tell.” Oh, sweet Christ! She had to be talking about my niece and that thought sent an additional surge of blood to my already aching dick. With the pad of my thumb I rubbed her lips, spreading her saliva across both of them and then tried my best to kiss them dry. A low growl arose from her throat and fueled a fire in me that really didn’t need any more fueling.
With my right hand I reached through the front of her legs and grabbed my dick. I was in a perfect position to pull the length of it up tight between her pussy lips. She was open and very wet by now and so it was easy to slide along her entire length and I knew that with the slightest change in my angle I could be buried to the hilt with one stroke. But I was still in some control and so with a slightly different change in angle I was able to rub my now wet dick around her clit. Not long stokes but short, firm ones and some side to side movement with additional pressure from my fingers.
After just a moment or two Sherry grabbed my ass, took a deep breath and had an orgasm that I could tell was an intense one. I could tell by the fingernails that she dug into my ass and I could actually feel her pussy lips squeezing the top of my dick. When she finally exhaled I could still feel her contracting and I couldn’t take it any more. I pulled back a little and with a little upward pressure from my fingers on my dick I was in.
I heard a deep moan and it took a second for me to realize that it was from me. Usually I like to tease a lady just a bit by pushing just the head of my dick in and then pulling it out a few times but my need was so great at this point that I gave up all pretense of control and began burying myself to the hilt with each forward thrust. On every third or fourth stoke I would hold myself as deep in her as I could. She was so warm and moist and tight that I couldn’t get enough of the feeling. The pressure building wasn’t just in my dick or my balls but also in my head. My ears were ringing and I was finding it difficult to take a full breath.
And then I guess Sherry decided that she wasn’t ready for things to be over and took matters into her own hands. So to speak. By simply taking her right leg off of mine and closing both of hers she not only effectively trapped me she also shortened the possible depth of my insertion. As hard as I tried I couldn’t move my dick any more than an inch or two and the additional pressure she was able to apply by squeezing her legs together was driving me fuckin’ insane. “Jesus Sherry, you’re killing me here. Please, open up,” I begged.
“Take it easy Sweetie. We’ve got plenty of time,” she said. Now where had I heard that before?
God, I really needed to cum! First I reached down and tried to lift her leg back up but she wasn’t having any of that. So then I figured I could play dirty also. With the two middle fingers on my right hand I started rubbing her clit high up on her pubic bone. She said something about me not being fair but she loosened up enough that I was able to go lower. I found that she was completely erect so I trapped her between my index and middle finger and began squeezing and rubbing her up and down and from side to side. Just a couple of minutes of this action and she was again breathing hard and on her way to an orgasm. She also put her leg back over mine giving me complete access to her depths again. I started pounding her a hard and deep as I could and my climax began building.
I would love to say that we had earth shattering, simultaneous orgasms but the truth of the matter is that I had absolutely no control left and I came first. And it was one of the most intense orgasms of my entire life. It’s really difficult to adequately describe a world class climax but I can say that I felt this one in every part of my body. And it just lasted and lasted. I held my breath so long that I nearly passed out. Once I came back down a little I resumed rubbing Sherry’s clit. She had been extremely close when I climaxed so it didn’t take her any time at all to go over the top. This time she came so hard and contracted with such force that she almost ejected my still mostly-erect cock from her pussy. But I felt it coming and pushed in as hard as I could. Deep inside of her I could feel every pulse and tremor and it felt wonderful.
I put my right hand back under Sherry’s shirt and cupped her left tit. With my face in her hair I went to sleep. I know that’s not very romantic but it had to be around 3:00 in the morning and we’d had a lot to drink and I had been up all day and I just drifted off. When I woke up it was around 10:00 and hot and I was still covered up with my pants down around my knees. No one else was around so I went to my place and showered. When I walked over to my sister’s later I found that Sherry had already headed back to Houston and my nephew back to Dallas.
I haven’t seen Sherry since then and have no idea how she feels about the night. Nor do I harbor any expectations that it will every happen again. But it doesn’t matter. I have a memory that not many men my age will ever have of a wild night of sex on a trampoline with a beautiful twenty one year old girl and two people there to watch. Yeah, my nephew told me later that he and his date actually sat up and watched us until we were finished. You’d think I’d be getting tired of him high-fivin’ me and saying, “You old horn dog, you.” But I’m not. And if I ever need a little help when masturbating I don’t have to work very hard to remember every detail.