Will you teach me how to please a woman?
Let me tell you about myself, first. At the time this went down, I was 19 yrs old, 5-7, 135#, 5 1/2" and wore very thick glasses. This took place around 1968 or so, and contact lenses were not developed for my eyes yet. So I looked like the sterotype of the Japanese man with coke bottle glasses. However, without glasses I could function socially, but forget about reading, driving, or working. I was skinny, but not weak, as my job of repairing and maintaining medical equipment involved some lifting, stooping and bending on a daily basis. I considered myself very average in all respects, and did not stand out in a crowd, except for the goggles.....
As a teenager, I led a very sheltered life and was still a virgin at 19 yrs old. I was an electronics nerd throughout high school, and while I asked out a few girls, nothing serious evolved and certainly not loosing my virginity. My glasses kept me out of the military draft, so I went into the workforce right out of graduation from a technical high school. My family could not afford college, so my plan was to work at a technician level with a company who would pay for my degree.
The town: The town is in the Northeast and is an old established very religious one. Very religious, where there are NO adult bookstores or adult entertainment places. In fact, if you wanted something such as a Playboy magazine, you had to drive to another town. If you suscribed, the mail personel would know and it would be all over the town in a hurry, you would be shuned. Sex was not even discussed in the locker rooms of either sex. Prudes! My family was no help that way. One time when I was 16, I woke up with "morning wood". My mother opened the door to roust me out of bed for school. She saw the tent in the sheet and said "If you have to pee, go do it and get dressed." Kind of makes you wonder how they had me......
I did not socialize much outside of my nerd buddies. One day we got a new guy working for us who transferred from out of state, and after 2 weeks he got settled in and posted a notice of him throwing a party at his place. I decided to go there. The party was in an apartment conplex near the hospital, and I knew that a lot nurses lived there, because when on call, they had to be less than 5 minutes from there,(or stay in the hospital dorm which was like an Army barracks) and I thought it may be a good way to meet some girls. The group there seemed to be 75% girls of all ages. Most guys were from my job, and I knew them.
So early on I got a beer, because I was on call that weekend and had my pager. If you showed up even mildly drunk at a customer location, your job went away on the spot. So with beers I could take a few without being blasted due to my fast metabilism. While sucking down a beer, I was standing next to a passageway and could hear 2 women talking on the other side. I ducked my head arouned the corner and saw them. One was about 5-1, short but thick hair in a pixie looking haor-do, very cute face, small breasted and looked like a gymnast with a very tight body from what I could see. She was wearing the hospital uniform: White loose fitting blouse, skirt just below the knees, and knee socks. The hospital was owned by the Catholic church, and the hospital personnel dressed like the catholic girls in school. The other woman was older, about 40 and on the heavy side, but dressed like they did back then in jeans and a sweatshirt.
The conversation went like this, with the small one first. "How are you doing, having seen you in a long time?"
"Really good, Cathy (later found it was the samll ones first name). How about you, did you get re-married?"
"No. But if I can't find someone soon, a good lay would be appreciated," They both laughed.
Then a lot of small talk and the larger one said "I have to get to the hospital to work see you later."
So I removed my glasses and walked thru the opening and headed to get another beer, trying to look nonchelont, and took up a position near her. She looked at me, and and said "Do you work at the hospital? I see your pager is just like mine"
I told her I repair medical equipment and get there frequently. She said she works for a OB/GYN/Urologist who specializes in the reproductive system, and she's on call for those type of emergencies.
To break the ice, so to speak, I said "What emergencies, someone can't get it up?"
She laughed and said "Well sometimes, but they are seen there during the day. Sometimes we get injuries in that area of the body and my Dr. is in call for the surgery to repair it. I like your sense of humor. The people I work with don't have a sense of humor, very straight laced."
She told me that she had been into an automobile accident and it required removing some of her reproductive equipment to save her life. She could have sex, but not kids. Her husband wanted kids and would not adopt, (Macho man) so he divorced her. The settlement paid for her to get a B S degree in nursing. She chose this specialty based on her medical problem.
She said "In this town of Victorian prudes, there are many newlyweds who do not have any idea of what to do to start a family. This is beause the school system being run by prudes, does not teach sex education, and who can you ask-- your priest? Parents? and even talking about it is taboo. We have many patients who come in there to find out. I mean we don't jump into the sack with them and after doing them say 'See?'. We use a book and discuss with them what to do so they can go home and try it. Since it's taught in church and home that sex is taboo, and its there for a purpose, none of which is for enjoyment. The patients come back and say we did not know its so much fun."
I said "I hear that. I hope you don't get mad at me, excuse me, but I overheard your conversation with the other woman an hour ago, and I would guess that would make you kind of horny talking about it all day and not getting it." She responded by a quick kiss in the lips and said "Got that right."
"My friends brag about doing some girl, 10 minutes, zip up, and go home. They seldom talk about a lasting relationship and I would guess that women want to be satisfied instead of a quickie?"
She said "Right on."
I said "Thank you for being honest. My turn to be honest." I took out my glasses and said "I wear these most of the time. It repels women to look into my eyes and have them magnified 3 times. I have removed my glasses for tonight" I put them on and she said " I see what you mean. Without them you are much better looking."
"For that and my shyness, I am a virgin. I would like to learn how to please and satisfy a woman, and maybe I can form a lasting relationship with one. Not knowing what to do, when we got to that point, I bailed out. I feel if they are satisfied, I will be, knowing I caused theirs. Also if the oppurtunity presents itself I doing want to look like a moron and embarass myself. Would it be possible to get one of the books you talk about?"
"I think I can get one for you" She took a piece of paper out and wrote her phone number on it and said "Call me Monday evening, and I'll meet you somewhere to give it to you. I will get pleasure knowing I am going to help make some woman very happy in her life. I need to get going, as I start work at 7:00 tomorrow. Call me."
So Monday after dinner I called her, and she told me to come to her place. She handed me the book and said "Take it home and read it over. Jot down any questions and call me I will answer them. Meantime, would you like something to drink?" I said coke would be fine. We talked. She liked the same TV shows, her record collection was of many of the same artists I liked, and it became obvious we had a lot in common.
A couple of hours later she said "Getting back to the party and what you heard me say, I am intrested to helping you learn to please a woman. I like you. You are nice guy, not pushy and we have many things in common-- same likes and needs. Maybe with live on-the-job training." She had a big smile after that.
"You mean..." She cut me off and said "That's exactly what I mean. Some ground rules:
“1 With this prude town, if they found out I was even just dating a man half my age, I would be fired from my job and run out of town. So this stays just between us. No bragging to your buddies, no one." I nodded my head yes.
“2 We will get some kicks, laughs, and experience, no falling in love; for the same reasons." Again, nodded my head yes.
“3 I do not need any contraceptives, but I will train you how to properly use them. Its not as easy as it looks. Remember, my Dr gets the people whose contraceptives failed...." We laughed.
"Go home and read up. Call me Thursday and I will know my weekend schedule."
As we walked to the door, she kissed me showing me she was serious about this. My dick quickly agreed.....
I called on Thrusday, and she said Saturday evening at 9 PM. I read the book through about 5 times. It started with foreplay, went into the missionary position, then into other positions. Last it discussed Oral sex. I work with manuals (equipment, that is) in my job, from all over the world. I can recognize they way its translated into English, and its origin language. This one is definitely French. Hence, the oral sections. In our part of the country, being prudish, oral is for whores, or gays and lezbos who are grouped into "queers" (terminology of that time). "Nice" girls did not do that, even AFTER marriage. So this is getting very intresting. One of my older friends said that doing oral will assure lifetime sex.
Saturday evening, I arrived and she sat me down next to her on the couch and said " I am going to do this in the order of the book chapters. I usually do this at work with the woman. The Dr. prohibits cross gender instruction classes. Lets start with foreplay. Pretend you are on a date with me."
"My pleasure"
She started kissing and carassing without sexually touching. As it evolved, she said "You got that one down OK. Now, listen. While kissing move your hand toward her breasts but do it slow. This gives the girl the oppurtunity to say no. If there is no resistance, cup it thru her blouse, and if she says no, stop. If she smiles or does anything but smacking you, she is willing.
I said "I will do that with my glaswses off so they won't get broken." We both got a laugh out of it.
I did as she said and she started purring. Said something under her breath like: "Its been a long time". So the kissing and feeling also got my motor running, and my dick at full mast. She rubbed my chest near my nipples and it felt great.
After a while she said to slip my hand under her blouse and do the same thing to her and roll the nipples between your thumb and index finger." I did so and she moaned. She then said "As you can hear, us women make non-verbal sounds which indicate us being pleasured. Use the sounds as you guide to go on. Unbutton my blouse, button by button starting at the top, with your other hand."
I did that and she shifted to allow me to remove it, so I did so. She said "You are catching on, fast."
After removing it, she unbuttoned my shirt and lifted it over my head. It was deposited on the floor along with hers.
She said "Pick me up and carry me to my bed." and pointed to the door. I did so, as she only seemed to weigh 90#. As I placed her on the bed, face up, she pulled me on top of her, and we resumed the kiss and grope session, and she said, take down my skirt and panties. By the way, womens skirts have the zipper on the left side. Then I will take down your pants and boxers."
She moved so to make it easier and then I positioned myself for her to do so. I noticed she was very hairy down there and held my eyes there a while. I looked at her nad she said: "You like?" I said "Excuse me for staring, this is the first live one I have ever seen." She said " I guessed that, now, I want you to curl your long finger, like saying come here, and then put it into me down there (pointing)and gently rub the inside of me. I am already wet, but I will get more wet and make insertion easier. I fingered her gently and she started a flow going.
She said stop! I though I did something wrong. She said "The womans clitoris is the most sensitive part. You wanted to learn how to pleasure it, so I an going to place your finger to locate it, then rub. Some women like it very gentile and some like it rough. This is something you and the woman came come to an agreement on how heavy it gets."
She placed my finger on the little nub and I started to rub it. She said "Up and down, sideways, whatever. Her sounds and lubricant flow is your guide as to how much shes pleasured."
I ramped up the motions, and suddenly she let out a squeal and the fluid gushed out. She was breathing hard and red faced. She said "Good job. That is the first orgasm I had in 4 years, and it was a good one."
I held up the finger and said "I AIM to please." and we both laughed.
She said "The woman may also stroke your penis while you are fingering her. This is definitely a sign of her being turned on wanting *it*.
My dick was so hard it hurt. This was blue balls and blue dick. She said "Now we will have real sex. I want you to mount me missionary , but do it slow. two reasons: I have not had any sex after they accident surgery, and you are inexperienced. I don't want you to ram it in and possibly injure either of us. For you, slow will allow you to savior the moment."
"I get it. I just want to say this. This comes from here, (pointing to my heart), not here (pointing to my crotch). Although I have only known you about a week. I am glad to be giving my virginity to you. You care about other people."
That got a passionate kiss and she said to put it at the opening, and she will guide it. I slowly pushed it in slowly, until my pubes touched hers, or in slang terms, balls to the wall. She was tight, but very wet. This said she was as into me as I was to her. She said "Ok, now do the stroking. Gently at first."
I said "I may be inexperienced but not that dumb. I was savoring the moment" I started stroking and after a while she said "faster". She started pumping to meet my strokes and I knew this was what its all about-- two people mutally pleasuring each other. After a while, I said I am going to cum. She said "Please." When I started to cum, she had this big-time orgasm, while I came into her with much more stuff then I have when masturbating. I totally drained myself. I lay there panting and sweating, and she also did, wet with both of our love juices. We lay there for a while holding each other, kissing and foundling.
She made a growling sound, then said "You did very well for your first time. I am going to enjoy this as much as you are. We need to clean up before you go home. Know this: the odor of sex is unmistakeable, and your parents will know. Want to join me in the shower?"
I grabbed her hand and nearly dragged her into it. We soaped and washed each other and we discussed the sensitive parts of both man and women. After drying each other, she said "Next Saturday, I want to skip to oral. Doing oral on a women will make her want you for life. Re-read that section.”
I said "OK see you then", and we embaced into a 5 minute kiss (and grope). I went home.
During the week we talked on the phone a few times and got together next Saturday night. She had a small glass of wine for each of us and said "Lets go over this before doing it. If you read it over, you must have second thoughts about putting your mouth down there, as most men do, and the women thinking of putting that "thing" in their mouths. I want you to try it. If it repels you we will do something else. I also have not done this before, as my ex did not want to do this or receive it. Religious reasons you know. We will go in the bathroom and shower together and clean up the areas we will use. Any questions?"
"You just answered them. I'll try it. Just teach me enough so I don't look like an idiot if I do this on some other woman."
She said "I'll do that."
With that, she took my hand and we stopped in the bedroom, just long enough to shed our clothes. I noticed she had trimmed her pussy. I must have stared at it and she said "That will make it more desirable for you." I shook my head yes.
Then I asked if I should trim mine? She said it don't get in the way on a man as it does on a women. I nodded yes.
We washed each other as she wanted to see what I learned about doing a sensious wash. I got an "A".
We went to the bed, where she had me sit on the edge. She said "I will do you first. As I am also new to this I read the book, and please give me feedback. Tell me when you are going to ejaculate. And watch how I try to maintain eye contact with you to "read" your facial expressions. And when you do me, try to maintain eye contact with me. It shows the other person you care."
She licked the head and paid attention to the sensitive underside. Then she put it in her mouth and tried to deep throat it in one move. She pulled it out, gagging. I said "Like I did to you last week, do it slow and get used to it before proceeding."
She tried it again slow. About halfway in, she was maintaining eye contact and her facial expression said she was enjoying the hell out of it, as was I. She got the whole 5 1/2 in, and the head was in her throat. (Remember, 5-1, 90#). She worked it slowly and very sensuously. In my mind, this is as close to excasy as it gets; all I have to do is stay hard-- she does the work.
I got close to cuming, and said so. She pulled off me, put her hand over the dick's head and used her hand to finish me. I came into her hand, which dripped all over my dick and lap. She said "Excuse me, but in reading the book, I wasn't sure if I could swallow." She scooped up some of my love juice and tasted it. She said "A bit salty, but very good tasting. Next time I will try swallowing." She did put her mouth back on it and cleaned me off. "Yes, next time I'll try to swallow."
Now she traded places with me. She told me to finger her for a short time and get her good and wet. After that, I took my fingers to my mouth and tasted it. I raised my eyebrows and said "Not bad at all" Then she placed my head down there and she said "Remember what you did with your finger, do the same thing with your tongue."
I got down there and started by licking the outside and then into the middle. I mentally noted that the trim job was a good idea, as I was taught to floss after eating, not during.....
I progressed and she said "Now lick and suck on the clitoris. I will guide you. And while down there get a good look at it for future reference. On a woman it enlarges like a man when aroused, but not as pronounced."
I found it, licked and sucked on it. Eye contact said she was in heaven and her love juices were flowing. It enlarged a bit as she said, and I sucked on it a bit harder. Her moans said I was doing it right. After a while I put my finger into her love hole, and did a "come her" finger crook and found the "G" spot. I rubbed it a few moments, and she stiffed up, put her hand over her mouth, gave a muffled scream and squirted on my face. She shook a while and said "Where did you learn that? It wasn't in the book?"
I said "I don't know. Remember, I am a techno-nerd, and it seemed that if either fingering or oral hed you orgasm, I though that both together would cause a bigger one."
"Let me tell you, it did."
"I noticed your very subtile hint"
"She said "Subtile as a blowtorch."
I continued until she came again, and she said she was a bit too sensitive. Lets rest a bit and try mutual oral, or 69.
I said "Question time. Doing oral is the most pleasurable thing for both man and woman. How come it is looked very down upon and is considered taboo here?"
"Good question. Here in the US we are kind of Victorian prudish in our sexual practices, as compared to Europe and Asia. For instance, in many places other than the US, if you go into the rest room, there will be two doors marked man and woman in their language. Both doors open into the same room. There may or may not be stalls with walls or it may be toilets in a row along a wall. In some countries, arranged marriages are common. The woman is raised to serve the man and she is the housekeeper, child raiser, and cook. If the man wants to stop off at his girlfriends for sex on the way home from work, its condoned, even by the wife. You see, they separate love and sex. So when they do oral its a way of showing appreciation of the other person. Granted, not all countries have this, but the attitude is there. In some places in Scandinavia, the farms are huge and most do not go into town a lot because of the heavy snow. So if you visit someone, its for an overnight. They put the single men up with their oldest daughter because she must get married first."
"Sort of test driving a car before buying it?"
"Exactly. The mothers teach their daughters how to pease a man. Here in the states, no way"
Now she motioned me to lay on my back.
She said "Do you remember in the book the picture of 69?"
"Yes, vividly"
"Good. Heres how its done. The heavier person is on the bottom, and the smaller one on top. I will take yours in my mouth and then adjust mine to your mouth. Just do what you did before and I will do the same. In this position, maintaining eye contact is almost impossible, however, the fact of mutual satisfaction will be judged on non-verbal sounds. You mother must have taught you not to talk with something in your mouth?"
We both laughed. I said "Cathy, you have a very warped sense of humor, just like me. I love it."
I laid back, and she crawled over me and positioned herself onto my dick. I placed my hands on her hips and guided her to me. I started licking and fingered her at the same time, and she sounded like she was really being pleased. I made some sounds to inform her. After some time, I tensed up and shot my load into her mouth, it was somewhat less than before, but still a lot. She tensed up and flooded my mouth and face. She rolled off me and said "That was great. Having you is one of the best things that happened to me."
She cleaned me with her mouth, and I did as much for her as I could. She said "Next time, we will experiment with other positions. If it would be OK with you, I would like to try it with me on top?"
I said "hell, yeah."
She said "you are too eager."
"hell yeah." We both laughed.
She said "Mostly all men in your age group are like that. in one word, HORNY. Women are most horny at about 38-40 yrs old, so we are both at our peak, sexually, medically speaking, and horny."
I said "I understand. We both are enjoying this a lot so what's wrong with it?"
"First, this is a town of prudes. Secondly, I am twice your age, going along with the prude factor."
"OK."
We did our clean up shower and did our "good night" 5 minute kiss.
Next time, she said she wanted to cook dinner for me before we entertain ourselves. She made a meatloaf which is my favorite, and said "I made this because it was my favorite.” Which I re[plied "Mine too. I am a meat and potatoes guy."
I struck up a conversation at the table. I asked her "Lets take a hypothetical case. Let's say there is a couple with a big age difference, like us. Yes, I realize that in this town its taboo. However, what if both want to relocate to a more progressive town, where it would be more socially acceptable and live together or marry."
"I know you mean us. I also thought about that. Both of us can get work almost anywhere. Even small towns have nearby medical facilities. And your job can even be home based. I want to think about this and don't bug me about it and I will let you know when we can further the conversation. I have one question-- Are you OK with not being able to have kids?"
"I knew that would come up. We would have each other. If we needed the patter of little feet, we could either adopt or buy a dog." She was sipping her wine and spit it out and laughed.
She, "And you commented on my weird sense of humor-- but I got the message."
Afterward we went into the bedroom, and she opened "the book" to the picture of cowgirl. Back then it was called 'woman on top'. I lay in the bed, and she started me with a blow job to get me good and ready, while I fingered her. She had a good flow going and moved over me. She took it in her hand and adjusted her position and slowly sank down on it. She said "I did this slowly. If it was not lined up properly, it could cause injuries to both of us. Tearing a muscle in the penis could result in permanent injury and a lot of pain."
"It hurts just thinking about it."
She worked it in her using her leg muscles and just like getting a blow job, all I had to do is stay hard. We both groaned, and made noises and maintained eye contact. This was as good as it gets. Unlike masterbation, when you cum, there is someone else to share it with....
We did some other positions later on. Rectal was not discussed in that book, and at that time, it was only considered for "queers" (dialect at that time).
I grew a mustache and looked a bit older, as my customers commented on my looking too young to repair medical machinery. (In fact, I was asked for proof-of-age at bars until I was over 40. Cathy's petite stature made her look younger, so we looked like a mid-20s couple. We went on dates on the other side of town. We agreed to show no signs of affection in public, and our story if questioned was we are cousins from different towns. One time, my company sent me to a town about 100 miles away to fill in for 3 days for a man who was at a company school. They put me into a motel; she got some vacation time and went with me. She had her wedding rings on so it was not questioned, and this town was not prudish like ours.
Besides the sex, this was my first time actually sleeping with a woman. Masterbation don't keep you warm at night. The pleasure of being woke up be being blown revelie.... The closeness of being with someone like that, well-- you all know what it's like.
She bought some new clothes which were more like what 20 yr olds wore, and looked damn good.
One day she says "I have re-done myself and gained more confidence on myself. A co-worker asked me out next Saturday night. I will let you know if it clicks for me."
I said "Bringing the book?"
She laughed "He's about my age but he's very sexually inexperienced. A momma's boy, but she told him to go find a wife. I'll play this by ear. Now that said, we need to talk seriously about us. I thought this over very carefully. If we adopted, when the child graduates high school, I would be almost 60. Other kids would be calling me her grandma. And refer to me as your mother. I do not want to leave here because my family and friends live here. I must say this-- I think we both broke one of my rules-- we both fell in love with each other. However, as I said it would not work." Then she started crying.
I said "Aside from the 'new toy' aspect, I would have to agree with you. We had one hell of a ride, and I will never forget you. I knew this day would come. Loving someone is knowing when to let go. Although will take me a while to get over it."
It did take a while, but I got back into my routine. I made service calls to her hospital, but she was usually in the Dr.s office with patients. I called her once, a month later and she said it was working out with her new beau. I said that I would not bother her again.
A while later, my employer gave me a service call to Cathy's doctor. The receptionist called her to the lobby, and as she entered, I noticed she had a different wedding ring on. We went to where the machine was, and she closed the door. She said "God knows I wanted to tell you and have you meet him. I thougt it would be awkward for you."
"Yes, it would. Did he turn out to be what you wanted? Did you have to instruct him?"
She said "Yes to both questions, and I used the book. I have a finely tuned sexual partner, like you,."
"OK. If you are happy, than so am I." (I lied; I was NOT happy, as you can imagine.)
I seviced the medical machine and left. She did kiss me and say thank you for everything.
The main thing for me, was not only had I got supreme sex, but what I learned both in and out of bed, gave me the confidence to date and subsequently bed down women. Yes, I never forgot her. One thing which I came out of the short relationship with-- I knew what I wanted when I got married. I also knew the sexual skills can be taught, however, BOTH parties must be willing to learn. Cathy was small, whitty, had a sense of humor, and the biggie: she cared about others. I kept the book and I used it when I got married. I had it hidden, because every time I saw it I could not help but wonder "What if....", however, I did not let that consume me.
This story is mostly true.... There was a Cathy (Not her real name) amd she did teach me.
