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If I'd Known Then....
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Updated 9/08 [M 51] During the summer of my 12th grade year I had just turned 18 and was invited to a student government institute for the entire summer. As it turned out a 5 year older cousin lived only 3 blocks from the place the course was held which was about 5 hours from where my parents lived. Money was a little tight and staying
with my female cousin saved lots of money so that is what I did. Even though I
had a car and I was taking the car to my cousin's my parents both went with
me the weekend before the course started. On Sunday at lunch we all went to a
park for lunch and as we sat at the picnic table, my mother told my cousin to
make me behave and what ever she needed to do she had their full support no
questions asked. Little did I know what that would mean. My cousin was beautiful
and had a really hot body, so as a 18 year old, I was looking forward to being
around her. Just after lunch, my parents started to leave and again my mother
told Kay that anything she needed to do to keep me in line was fine with them. Kay said she would make sure I was good. To my surprise my mother walked behind me and gave me a
very hard swat on my butt. Kay smiled at me and my mother.
Nothing unusual happened the next week then on Saturday afternoon, I was doing
some of the reading that was required when Kay came to the door of my room and
told me to come to the kitchen. I needed a break and so I followed her to the
kitchen. Still on the counter was an open peanut butter jar and a sticky jelly
knife where I had made a pb&j earlier. She asked me if I thought she was my
maid, I told her I was sorry and started to clean it up. She grabbed my arm and
told me this was not the first mess I had left that she thought I needed some
punishment. She reminded me that my mother had said what ever was needed to keep
me in line. Then she told me to got to my room and take off everything except my
underwear and to bring her blue hair brush and come to the den. I begged her not
to spank me and she gave me a firm swat and she in a firm voice "NOW!"
I went up to my room and took off my shorts and tshirt and wearing only my
underwear came back down with the hairbrush she asked for.
Once I got back to the den she told me that not following her instructions the
first time had cost me my underwear to take them off and hand them to her. She
was getting ready to be the first female to see me naked besides my mother and
my doctor. I pushed my underwear off and handed them to her, she took them from
me and told me that I would not wear underwear for the next 4 days. I was uneasy
about the spanking I was getting ready to get when she told me to bend over and
hold on the the ottoman in front of me. I did as I was told and she told me to
spread my legs wide. Then she reached between my legs and squeezed my penis and
told me "If this gets hard, you will have to be naked every minute you are
in this house for the next week" I was already in trouble, I was getting
hard as she squeezed me. She laughed at me and said, "Glad you like being
naked" and started to spank me with the hair brush. I got 20 that were firm
but not unbearable.
As soon as she finished spanking me she told me to go clean up my mess and to
come back to the den. I did as I was told still naked. When I returned to the
den she had changed to a very tight t-shirt and no bra and real short shorts. As
soon as I saw her nipples sticking out from the t-shirt and my penis jumped back
to full erection. Kay looked at my erection and told me I had to keep that in
check that her mother (my aunt Judy) would be there in just a few minutes. I
begged her to let me dress and she said if I did that both of them would be
spanking my naked ass the rest of the day. She then told me to bend over and let
her check out how red my butt was. Once I was bent over she once again reached
between my legs and squeezed my penis. She said not quite red enough I will just
wait till mom arrives and spank you again. Then she told me to stand with my
back against the wall and my hands on top of my head until she arrived. Every
few minutes she would walk over to me and stroke my penis to keep it real hard until we heard thecar door close.
In just moments Aunt Judy opened the door and walked in with me standing there
totally nude and an erection as hard as I could produce. Aunt Judy said at
once,"Hmm someone has been a bad boy" Kay spoke up and said I had lost
my clothes for a week, and Judy told me to turn around and let her see my butt.
I turned around and Aunt Judy said that Kay had not been firm enough with me.
Kay said that she thought that she could help her with giving me a better
spanking and Judy told her that she had to learn to do it right if I were going
to live there all summer. Aunt Judy then asked Kay if she was going to do it
right or did she have to do it herself. Kay said she wanted to watch one time
and then she could do it right from then on. Aunt Judy sent Kay to the maple
tree in the back yard to get 5 switches. While she was gone Aunt Judy left the
room and came back wearing one of Kay's t shirts and a real short skirt.
Once Kay came back with the switches, Aunt Judy
told me to come to the ottoman and bend over and hold it. She told me to
spread my legs wide and once I had followed her instructions just as her
daughter had done before Aunt Judy reached between my legs and stroked my penis
and told me if this is still hard when I finish or if you take our hands off the
ottoman, she would give me 5 swats with the switch directly on my penis. She
stroked a few more times and then started to spank me with the switch. Not too
hard but it really stung. It went on for ever it seemed like and really started
to hurt, then with the aim of Robin Hood she let the tip of the switch hit right
between my legs right on my scrotum. Somehow I managed to keep my hands on the
ottoman, but then the very next one was much harder and again right on my
scrotum.
I dropped to my knees but kept my hands on the ottoman. She made me
stand back up and made me spread my legs wider still. Before the next swat she
asked me if I wanted the spanking to continue or if I just wanted to go ahead and take the 5 on my penis. I said I did not want any on my penis. Then she got a new longer switch and took the first swing, it wrapped all the way around my side and hit the side of my penis.
I jumped up and grabbed my penis and screamed. Aunt Judy just laughed and said
"ok here is a deal. Since you are not circumcised then you can take the 5
on your penis as it is natural or you can take 1 with the foreskin pulled back.
Which will it be?"
I knew that there was no way out of this because my own
mother had told me that she would spank my penis one time after she caught me
sneaking a look at her in the bathtub. I tried to decide which would be worse
and decided to take the one. So I told her just the one. So she made me stand
with my back against the door and my hands on top of my head then to my surprise
she told Kay to pull my foreskin back and hold it tight. As Kay held it back
Aunt Judy told me that after she hit it I could not touch it for 10 minutes if I did I would get the other 4. Then with perfect aim she swatted my penis right on the head with the switch.
Tears filled my eyes and I thought she had knocked it off. As I stood there for
the 10 minutes a puddle of pre-cum formed on the floor. And the pain turned in
to a deep sting, that was a little painful but mostly exciting.
After the 10 minutes my Aunt told me I could touch myself but I was not to move
from that position until she told me I could. She then looked at Kay and told
her that since she had not spanked me properly that she would get it now. Kay
stood up with her head down and said yes'm. Aunt Judy told her to go to the
dining room and undress. I could not see into the dining room but could hear
everything perfectly. Aunt Judy walked back in front of me and I could see that
she too did not have a bra on under her tshirt. Aunt Judy looked at me and said
"You can look at my boobs all you want and you are right I do not have a
bra on, but if I catch you looking up my skirt, you will get this kind of
spanking again at the end of the summer in front of your mother, sister, and
grandmother. I will even show you my bare boobs any time you want. But I want
you to know that there is nothing under this skirt and if you look you will get
what I promise."
Knowing what I know now, I would have looked!!
Updated 5/08 [M] If I'd known then what I know now, I'd probably have a coupe more relationships under my belt and more sexual partners. There have been many time in my life that I could have had have a relationship or at the very least, a sexual encounter but never materialized either because I played it too safe or was totally clueless of what was happening. (I was kind of a nerdy guy in my much younger days)
[M 54] Yes if I'd only known then. That would be thirty-eight years ago during the Vietnam war when I was stationed in Thailand. Being a nineteen year-old horny GI on my day off I headed to town with a little money, a bottle of booze, and a hard cock,looking for a good time. Well after a few drinks I ended up going home with a very lovely young lady. She wasn't one of the regular girls I normally went home with, they weren't around and I thought what to heck, right now a pussy's a pussy. When we got to her place we went through the usual ritual, she undressed me and than herself and we went into the bathroom and she bathed both of us. She led my hard cock and I back to the bed and this is when it started to get weird, or at least I thought so at the time.
She didn't speak much English and my Thai wasn't that good but she had me sit in the middle of the bed and cross my ankles, then she sat in my lap facing me. At first I thought this was great until I realized my cock wasn't in her pussy and when I tried to reach down and put it in her she pulled my hand away. Then she tried to get me to stare into her eyes and breath the way she was. Well being the nice guy I was I played along but I could never get the breathing part right or at least good enough for her and I would laugh everytime she would stare into my eyes, probably because I was pretty tipsy at the time. After about half an hour she became frustrated with me and climbed off my lap and proceeded to jerk me off. After her sitting on my lap all that time it didn't take long and my cock turned into a cum geiser spewing cum all over both of us.
Acting disgusted she took me by the hand to the bathroom and cleaned us of again and then back to bed. Again she started trying to get me to breath funny and kept pressing on a spot between my balls and my ass hole, and kept saying no cum, no cum. All I could think of was no cum my butt I want to fuck and cum over and over again. Well she gave in again and sucked my cock but to my surprise instead of swallowing my cum or pulling my cock out of her mouth and shooting it on the bed she shot my load all over her face and then began rubbing it around on her face with her fingers. I lay there in amazement while she laid perfectly still for about five minutes or so.
At first I didn't know if she had passed out or was really enjoying my cum that much, but then she sat up, wiped my cum of her face and asked me to leave. I got up and got dressed and went back to the base thoroughly confused but very happy that I had just got off twice with a very beautiful woman and she never asked for any money.
You're probably wondering what I wished I would have know then that I know now. Well what she was trying to get me to learn were Taoist and Tantric methods of love making. The Lotus position she had us in is considered extremely close an intimate and if I would have been more open to new things and been more patient she would have eventually raised up and took my cock into her pussy. Now after years of reading about and trying to practice some of these methods I wished I would have listened to her and spent more time learning what she was trying to teach me. It would have made me a much better lover overall. When she wanted me too stare into her eyes and I thought it was weird I now understand that the eyes are the windows to the soul and open up a persons deepest feeling which can enhance the sexual experience. Matching your breathing to your partners helps you both get your sexual energy in sync which is important when you join together; she climbs on your cock, and begin exchanging sexual energy.
The most important part I should have paid attention to was when she pressed between my balls and ass, she was right if you squeeze your PC muscle or just press on that spot with your fingers you can stop yourself from cumming and still have a very pleasurable orgasm and not loose your hard-on and you can keep fucking as long as you want. I didn't learn these things until about seven years ago, what a waste. I not complaining about my sex life, my wifes hot as can be and we have enjoyed learning fantastic things together. The only reason I learn the Taoist and Tantric methods is I started having erection problems and found some exercises to help me get my cock hard in some books that taught the Taoist and Tantric methods of sex. They helped my erection problems and improved our love lives greatly; my wife Di loves me being multi-ogasmic like her now, but they also showed me how much I had missed out on all these years because I thought the girl in Thailand was wanting me to do weird things.
Updated 1/08 [M 35] My first experience was with my friend's eldest sister. At that time she was 25-26 and I was 14....
Well sticking to the topic , If I had known then, I would keep the details only about this aspect only. Had I known the taste, I would have never said NO when she pushed my face from her breast to her pleasure valley..... At that time I thought V-area was a bad thing...... had I known at that time, I would have loved to taste her down there and play with her clit and lips.
She also invited me to kiss her hips and the back area to which I again said NO.... but if I get a chance now, I would not only kiss there, I would lick and put my tongue IN there too..... I concentrated on her breasts and then on entering her and just because of my lck of knowledge missed the chance to tongue her heavenly holes.
[M] I guess I'd have had a lot more "experience" if you know what I mean. I may have had more women in my life and perhaps would have been better able to get along with and make more women friends. I was always shy and never really developed any kind of friendships, let alone intimate relations, w/ women prior to my twentys. I was kind of a geek I guess. I think I may even have lost my virginity earlier.
Updated 11/07 [M 33] If I'd known then? Personally I would not have changed a thing. I never wanted to "play the field" as it were and have a string perhaps of lovers/girls in tow. I wanted to meet the "right" girl and work on things from there, so I saved myself and waited my time, and I'm glad I did because the wait was worth it. I lost my virginity to the girl who lost hers to me, that was what I wanted, and as time passed we learned about one another as couples do sexually, together and at our pace, comfortable with one another's body. As a result of this we have in my opinion something to be proud of. I got my wish. And had I a chance to go back on it all, I'd do pretty much the same again to have what I do today. As the French say, "je ne regrette rien."
Updated 10/07 [F 42] If i had known than what i know now i would have become sexually active at a younger age and i would not have held out for head over heels love. To be truthful in the end i was 21 and tired of not being with any one so i jumped a close family friend's son. i knew that he was 'so called' safe with no worry about aids or anything else and i also knew that he had wanted me for a long time. in the end we both used each other and 2 days later i meet my husband through his sister - she was going to marry his bother. Talk about an odd world.
Updated 2/07 [M] (M) About if we had known then what we know now, oh yes! Would things had been different back then. I know now I would almost with certainty had lost my virginity at the age of 19 with a living doll named Peggy. Her and that fantastic body of hers was so hot and ready but I just didn't know what to do to "break the ice", so to speak. All I had on my mind was to get my hand up her skirt to her beautiful inner thighs for a good feel of this. But, knowing full well that for me to had shoved a hand up there would had probably got me a slap on the face. Didn't know it then but I do now. The breast were the key! If only I had eased my hands around and started caressing on her breast through her top things would had sure been different. As it turned out back then I'd always end up dropping her off at her house and leave with a raging erection in my pants and not in her hands or in her pussy. If only I had known about tits being the key to what I really wanted which was in my case being legs and eventually, pussy! If not for the girlfriend I had THREE years later making the first move on me, I might had never got to feel some soft female thighs and got my first pussy. It was this later girlfriend that made the first move which was rubbing on my very erect penis through my pants one night while we were laying down kissing. I then FINALLY got my hand up a skirt and between a girls legs. It was seventh heaven! Needless to say, I lost my load of semen right there in my pants. At least, the door was open and I must had tried to make up for all those years of doing without with this girl. I spent the weekend with her and how she kept from getting pregnant I'll never know. I can't even imagine how much semen she had pumped into her that weekend by me. I was almost constantly in her with my penis and was almost sore from all the screwing and was completely drained by that Sunday evening. I don't think I could had gone again. But, anyway, I've been doing my best to make up for those early years of doing without ever since. But, if only I'd known. I know that with Peggy I would had "broken in" with the best. Oh, this girl had one beautiful body and that HAD to be some kind of pussy to be in!
