We currently have 44664 stories with more being added every day

Well Schooled in the Art of Pleasing a Girl

Posted by: Author: Age: 48 Posted on: 3 comments
0 likes 960 views Category: Masturbation Male-Female Tags:

I read a recent story about learning from older girls and it brought back fond memories.


I matured at a very early age I was jacking off and producing ejaculate probably 4 years before others in my grade. I used to sit back by the older kids in the school bus and listen to there exploits and go into school and stroke one out while the other busses were arriving. I did not think it was unusual at the time I just figured kids my age kept it private.

Because of hitting puberty early I was ahead of all the girls as well so I tended to socialize early on with girls 2-3 years older than me. My parents were very strict and I was not allowed to date until I was 16 (probably would have knocked up some girl)

I read a recent story about learning from older girls and it brought back fond memories.

When I was young I used to have a sitters until I was 15, I think I was kind of an oops because my sister is 8 years older than me. My parents kind of did there own thing, and so I had a sitter at least two nights a week. It had been my sister, when I was real young, but when she turned 16 and was allowed to date, she would not be caught dead sitting for me, which was fine with me.

I had two sitters that I loved and I think they thought I was cool to, because I physically matured early I was taller than they were, and because we lived in the country and there were no kids around my age I was raised with a much more mature prospective. I think my sitters thought of me more as a peer.

Elisa was my first crush. I would do what ever she asked I would constantly be rubbing her neck or her feet, if we watched a movie it would always be her choice, if we played a game it was what she wanted to play, I constantly asked her about her dates and what she had done with boys. She would compliment me on my being a gentleman. She was allowed to date but was just getting to the point of kissing. She said it seemed weird like he did not like kissing. I told her I would love kissing and she could practice on me any time. She was surprised. “really”. I said sure you’re my best friend why wouldn’t I want to kiss you. She leaned in and gave me a quick peck on the cheek. I said that didn’t feel weird to me. That was the nicest thing you have ever done for me. I leaned in and gave her peck on the lips. Then there was a long silence. She finally spoke. I really do like you and I really do want to get better at kissing but I’m your sitter and it wouldn’t be right.

I assured her that I needed to learn as well and I promised no one would find out. What better way to learn than from a friend. She hugged me a long time very tenderly; I would have done anything for her at that point. She set all sorts of ground rules. The first night we spent a half hour kissing and nibbling. If I had touched my self I could have shot and any instant.

I had a firm bed time at 10, if I was up when my parents got home Elise would get canned and neither of us wanted that. She would sit on my bed reading out loud from her romance novel and I would grind away at the mattress. She had to have sensed what I was doing but never said a word. At some point she would say I need to go down stairs. I always asked for a good night kiss. She obliged and the rules were one by one obliterated as I got to fondle her boob first over than under, she stopped wearing a bra and took to wearing shear tea shirt and a bulky sweater or sweat shirt for easy access and quick dressing if it became necessary.

At some point we had progressed to me suckling on her boobs and frenching. Her breathing got short and ragged. I swirled my tongue around her nipple and her breath caught. She trembled and although until that very moment I did not know girls could cum, I though she must have. Things went quiet for a while and I figured she was ashamed. I told her “no one will ever know, I love being with you” we cuddled for a long time after that. On successive nights I got so I could make her cum easily she would grind her clothed pussy on my leg with sweats, and I would suckle her nipples.

Then one fateful night we were dry humping and frenching and I could not hold back. I came and when it hit me it was like an explosion, far and away the best orgasm I had ever had, and the first with Elisa. She stopped grinding and said did you cum. I said yea I’m sorry. She was quiet again and I figured I had really blown it, literally. She then said is that your first time. I kind of chuckled at the thought, when I told her when I first started having orgasms and when I first started having ejaculations she hit me hard, calling me a liar. I assured her that it was true. It was like a million questions after that. I finally asked her if her first orgasm was with me, she said yes. I finally dawned on me that I might be kind of weird. I asked her not to tell and she looks at me like I’m a dumb ass. Then she rips down my shorts to see my cum. Holy cow is there always this much, I said it was my best orgasm ever. She beamed. Then she leaned over and inhaled “it smells like cleanser what does it taste like.” It had never occurred to me to taste it. “I joked back I don’t know what does yours taste like. “Like sweet-tarts” I think it dawned on her and I at the same time, that she had just admitted tasting her own girl goo.

I was at full staff again. She noted “you can’t keep a good man down” I said “not when you are around”. She then asked if I could cum again. Again this was something I had never tried. I said “sure, I suppose so, I don’t know, can you” She smiled her nipples were so hard and distended I suspect she could cum in an instant. At that she jumped up and I said, where are you going. She came back with a warm wash cloth. I almost came again from her washing me up. Then she climbed back on me and started grinding away on my bear penis, no penetration, but I was in heaven if I had not just cum I would not have lasted 10 seconds. Inside of three minutes she was shuddering in another orgasm, which took me over the top. As she began feeling me cum, she jumped up. I think partially out of fear of pregnancy, and partly to see me shoot. I grabbed my dick to maximize the result. There was not as much cum this time, but 3 – 4 good ropes hit my chest.

I ran my finger through it and put it in my mouth. She looked at me quizzically, and I said “salty.” I grabbed her hand and wetted her fingers with my spunk and brought it to my lips I sucked them clean. I gathered another sample on my fingers and held them to her mouth. She just held out her tongue and shook her head. “no way” I said “I’ll taste you” No you wont. That’s enough for one night. Just then we heard the front door. That was as close as we ever came to being caught. Luckily my parents did not check on me. The room reeked of sex.

When Elisa went off to collage according to my parents I still needed a sitter if they were away over night. I should say by that time I was 6’ and weighed 200. I had a job after school splitting fire wood, and I helped local farmers hay that summer. I had the upper body of a lumber jack. I was tanned and ripped.

Susie was the new sitter. She came to stay when my parents were to be away for 10 days. When we met she was taken back. She asked my mom how old I was. She told her, and said don’t let his appearance fool you, he as immature as a 12 year old. He would eat pizza and drink chocolate milk for breakfast lunch and dinner if you let him. Susie was cool. I doted on her just as I had on Elisa on the third day she was allowing me to massage her back with her shirt up and bra undone. She let me stay up as long as I wanted. She would go to bed and I would jack off to computer porn in the den. She asked about my girl friend. Until only recently I had all my needs taken care of by Elisa. There was one senior I was interested in, but she would not date me because of the stigma of dating a sophomore. I told Susie that I did not like any of the immature girls my age. I also shared that I feared that my inexperience would be a problem once I got to collage. Susie suggested I could learn a lot from the internet. I suggested I needed someone to show me the ropes. Judging by how her nipples were responding, the prospect excited her.

She was only three years my senior. She had a job and looked to be in her mid 20 though she was only a year out of high school. I asked her about her love life, she had just broken up with her immature boyfriend when he went back to collage. She thought he never intended a relationship past the summer, but never told her until it was over. I told her she was too good for him, and she was super hot, and would have a hunk in no time, “till then you can have me. Why don’t you go take a bath and I’ll make dinner.” Despite my pension for pizza, I make mean spaghetti and meat balls with decadent garlic bread. She came down after two hours in sweats and a robe. She smiled and thanked me and said “I needed that, what’s for dinner”. She was surprised that it wasn’t pizza and when I brought out a 12 ingredient tossed salad by candlelight, she said I think your mom was just pimpin you a girl friend. I said so then you will play along and say that I’m an immature child and assure her that I should not be left alone. We both laughed. We both had some wine with dinner I said my parents let me when they are at home. She was not of age either so celebrating the taboo had her jazzed as well. I rubbed her neck as she did the dished. Then I asked for a lesson about girls. She laughed and said you are doing just fine sir, just keep doing what you’re doing. I asked what about kissing though. “Would you go out with a guy who was a lousy kisser?”

She allowed as such as that was an acquired skill. As she finished the dishes she enlightened me with all her pet peeves in kissing. Shave before the date, Brush your teeth, no garlic or onions all day, don’t start with a tonsillectomy, and don’t ignore the neck and ear lobes. As I massaged away, her voice dropped away and became dreamier. Light pecks to begin, run your hands through her hair, hold her like she is your only desire. When her breathing changes, then you can explore a little more. Don’t rush it make it last. Then she leaned back on me and becomes aware of my hard on. She turns around and gives me a peck on the lips. She says why don’t you go take care of that and we will see about your lesson. In my experience unless you don’t need it, you won’t take the time to give a girl what she needs. She swatted me on the butt and said run along now.

I suggested it would go a lot faster if she would help. She laughed and said “I’m sure it would, this is to be a lesson about how a girl wants to be treated. I don’t need any lessons on how to treat a guy.”

I moped up stairs half intending not to come back down. I rather mechanically stroked one out. As I got closer, I imagined Susie jilling down stairs, thinking of me. I busted a pretty good nut in no time. I snuck back down hoping to see her priming her pump. But she was at the computer reading. As I walked over she asked if I felt better. I admitted I was still horny, she smiled said let me see. I guess I wasn’t tented too badly.

We started with what she called the first date kiss. She was very mechanical about the explanation it needs to be long enough to imply some definite interest but not so long as to suggest that you are expecting more. It can be moist, but no tong. You’re a tall guy you should allow her to be up one step, so she feels your equal. Don’t hold her so tight that she can’t get away, but definitely hold her. Ok let’s try.

I immediately swooped in and kissed her on the lips. She was taken back, she wasn’t ready, she was not on a step and I had not held her. She admonished me, this is a girl you care deeply about and you just spent all afternoon with. You want her to know you desire her, but she is in control. She walked me over to the steps and assumed the position. We were eye to eye. This time I waited we looked each other in the eyes. I waited until she closed her eyes, “Susie I want you so”. I kissed her on the lips with two short tugs on her lower lip as I drew away. “Much better” she said “let’s do that two more times to make sure you have it”. “Say the word and I’m yours” a duplicate kiss with top lip in play. She was definitely I little distracted, she said nothing I looked her in the eyes and said ‘Please kiss me like you need me” That did it we were all over each other. Just then the phone rang. I was late enough that I would need to be home. So I had to pick it up. It was my parents checking in. They asked how Susie and I were getting along. I allowed as such that she was a slave driver she would not let me have my way with anything. Mom chuckled and said good girl. Susie got on the line a bit and assured my mom that she would keep me in line.

The rest of that week we expanded my education and polished my skills in the end Susie said I was a born natural, and I would have no problems when I found a girlfriend. I asked her if she was available. We were friends with benefits, until I started taking some courses at community collage my junior year of high school. Apparently there is no such stigma of dating a younger guy in collage. I continued dating over my age till I met the girl who became my wife. Tracy is 3 years younger then me. It really felt like I was robbing the cradle then, and even more so as the years go on. I have continued to look older and perform as if I were 25 % older than I am, and Tracy has barely aged a day. It’s fun to see her shoot down young studs thinking she is a hot cougar and I’m her old man. Tracy says she decided I was the one long before I proposed, she had never had a man who was more concerned about her than he was about him self. We still make out and mutual masturbation is a big part of our sex life, in part because I can’t perform as well any more. I’m looking into h hormone replacement therapy. I’ll let you know how it works out.



You must be logged in to post wall comments or like a story. Please login or signup (free).

Other Stories You May Enjoy