After School Sex Tutor
This happened many years ago and it remains to this day the most memorable sexual experience of my life. I was just sixteen years old and living with my mother and younger b*****r in a South American country of my parent’s birth for one year. I was miserable, separated from my friends, going to an all boys prep school, and still a virgin. I spent the first 8 months trying to get laid without any luck; with girls my own age, older girls, I even went looking for hookers without any success of ridding myself of this terrible affliction of virginity. Then my luck changed in a big way and from a most unexpected corner, my own f****y.
She was related to my mother by marriage, a second or third cousin. We met Anna and her husband for a spring weekend drive through the city. Anna was about thirty, with shoulder length light brown hair, olive skin, slim with smallish but shapely breasts and a wonderful smile. She was attractive, you would have given her a second look if you passed her on the street. Although at my age I would have looked at an ugly woman and gotten hard, I was so horny. She was very outgoing and talkative, asking questions and laughing easily. He husband was older, and a bit dull.
We all went for a drive. I don’t remember where we went that day, but I do remember her sitting in the back seat of her husband’s car with my little b*****r on one side, me on the other. While she was talking the car took a sudden turn which threw her into me. Her hand gripped my leg as she let out a short cry of surprise. She kept her hand on my leg and squeezed, looked at me and smiled. Just then she noticed something outside the window and leaned over me while pointing at it, as she did her breast pressed into my arm and the hand that had been on my leg was now for a moment in between my legs pressing back and forth over my encased and quickly aroused cock. As quickly as she had moved her hand between my legs she moved it away again and leaned back in the seat. I looked at her and she smiled, then she grabbed my hand with her hands and gave it a quick squeeze. I really don’t remember much of the rest of the day, my head was in a fog. I know I wanted her to touch me again, and I took every opportunity to stand close to her the rest of the day for a repeat of what happened in the car but it didn’t. We parted and I thought that was that. How was I, a sixteen year old k**, going to set up a meeting with an adult married woman? Beside, maybe it was all in my imagination, perhaps it was all very innocent. That night I had to rub one out thinking about her.
A couple of days passed. While leaving my apartment building, dressed in my blue blazer, and gray pants, heading off to school, Anna approached me, out of now where it seemed, very excited, talking very fast (she latter admitted to me she was very nervous). What a coincidence it was that we should meet on the street like this, she was in the neighborhood looking at an apartment to rent and would I be a dear and go with her and tell her what I thought of the place, it would just take a minute. Before I could really reply that I had to go to school and was late already, she was pulling me by the arm down the street. Anna was dressed in a bright sun dress, perhaps too light for the season, showing lots of skin, with her hair and makeup just so, as if she were going to an interview. In a sense, she latter told me, she was. She assured me it would not take long and that she really valued my opinion, although I couldn’t imagine why.
We stopped in front of a place just four blocks from where I lived. It was an old apartment house without an elevator. We walked up three flights of stairs, Anna talking very fast the entire way, I said maybe three words since our “chance encounter”. After taking out a key and opening the door to an apartment that looked out over a courtyard she practically pulled me in. It looked like an old woman’s apartment, which is what it had been, she had died and her c***dren were renting it out she told me. Anna moved about the small living room, showing me the tiny kitchen and bathroom. She pulled me over to the window that looked out over a courtyard. It was covered with those lacy kind of curtains favored by old women. Anna stood very close to me and looked me right in the eyes and asked:
“Well, what do you think?”
I am 5’7 and Anna was almost the same height. I felt very nervous all of a sudden standing there so close to her. I think I stammered that I thought it was fine or some sort of nonsense. She took my arms and placed them around her slender waist, then she put her arms around my shoulders and pulled me against her body. I would like to think that I moved to kiss her first but I think she was the one to first move her lips onto mine. We kissed lightly at first, then with more pressure, quickly thrusting tongues into each others mouths. Needless to say I couldn’t believe it was happening, I might actually get laid. She broke our lip lock and deftly took off my school jacket with its school emblem patch sown on the front pocket and threw it aside. Then she took off my clip-on tie and unbuttoned my white shirt. Then she did what I have wanted women to do ever since. She got her knees and unbuckled my belt, then unbuttoned my pants and pulled them down my legs, making me pick up my feet to take off my grey trousers and tossed them aside. She then proceeded to rub my cock through my underwear.
She began to talk about my cock.
“ It’s so big already. You have a man cock not a boy’s cock.”
She continued for a while stroking my cock. Then without warning she grabbed the elastic to my underwear and gave it a tug down to my ankles and again made me step out of them. My 16 year old cock was by now almost at full staff directly in her face. She began by fondling my balls, cupping them in her hand saying things like:
“Oh my your balls are so big and manly. I bet they are filled with beautiful hot cum.”
She then began to jerk off my cock but not in the rough clumsy way that girls my age had awkwardly jerked me off in dark basements back home. But gently, using her saliva to glide her hand over the head and down the shaft then back again.
“God you have a nice cock, a man’s cock. A cock that needs to be sucked by a woman’s mouth doesn’t it?”
I don’t think I could answer the question, my mouth wasn’t working very well, so I nodded my head in the affirmative. She smiled and then started to lick the head of my dick. Then she placed it in her mouth, gently at first, then with more suction, more and more of my cock disappeared into her mouth. They were slow leisurely swallows, with a slight head shake a couple of times at the apex to try and fit even more of my cock down her throat, until her nose almost touched my body. I have tried to teach that technique to girlfriends ever since by the way, with varying degrees of success.
I can only image what my face looked like when she would look up at me with my cock in her mouth. My eyes wide, jaw slack, she was blowing my mind as well as my cock. I don’t think I lasted very long, although she latter said she was surprised at how long I did last for a sixteen year old k**. I could feel the eruption build from somewhere deep in my groin. She could also sense I was close because she speed up her journeys up and down my cock with her mouth. Suddenly she stopped sucking and began rubbing my hard cock very fast with her hand. My legs shook, I closed my eyes and streams of cum shot out my cock. It felt like I was pissing because of the volume of cum that shot up from my balls. One stream of cum, two, then three, each accompanied by a shout of surprise, delight, then laughter from my sexual savior. I guess I must have moaned, but what I remember is that all the neurons in my brain fired at once sending shock waves through my body. I think I blacked out for a moment, because the next time I was semi conscious again, I was on my back on the floor, I have no memory traveling to the floor. When the fireworks in my brain subsided I opened my eyes again, I feasted on the sight of Anna gently stroking and licking my cock. My cum was in her hair, on her mouth and cheeks, and all over her chest and pretty sun dress.
She smiled at me and said,”so did you like that?”
We both laughed.
We talked for a bit just like we were, my cock in her hand, my spunk all over her.
“I want to be your teacher. Would you let me teach you about love making?”
I think I said something intelligent like “you bet you can”.
Class was in session. Well it literally was, so I had to figure out how to cut class that day. I remembered that my mother was going out all day, I would go home tell her I was sick and then leave after she went out. It only took about an hour an a half for me to go home fake my illness, then return to the arms of my love tutor, but it seemed like forever. I ran all the way back to that dead old lady’s apartment where my very much alive love professor was waiting for my sixteen year old cock.
When I got back, her washed dress was hanging in the kitchen to dry, and I found her in the bedroom wearing nothing but her bra and panties. I quickly undressed and joined her.
She told me that she could get away from her husband three times a week and that we could meet after I came home from school. That sounded like a wonderful plan to me. She admitted it had been fantasy of hers, to teach a young man the ways of lovemaking. I said that I would be the best student ever, in the history of education.
“Well then lets begin”, she said as she slipped off her panties and spread her legs and then her vulva with her fingertips to show me around the hood.
“This is a woman’s clitoris...” Soon I was licking and sucking my teacher to a leg contracting body shaking orgasm. My first exam and I aced it. If only chemistry was as much fun.
We ended that day with my first sexual intercourse of my young life, and about time. Just a straight missionary position but in the coming weeks and months Anna showed me many more.
Our lessons would begin when I got home from school. I would tell my mother I was meeting a friend and would have dinner with his f****y, then run the four blocks. She would have to leave around 8pm which gave us a good four hours a day for my lessons. We would take time out to eat a little something she cooked us but then back to the books, between my legs or hers. It was a dream come true. She told me her husband was impotent and wasn’t much interested in sex anyway. She had married him when she was young and dumb, but she was trying to make the best of a bad situation. His loss was my gain.
By the end of our first full week of study, she had shown me the finer points of anal sex (use lots of lube) and the 69 position. Needless to say I failed every subject at school that year, but got straight A’s from my favorite teacher.
Before I knew it we were getting ready to return to the U.S. and truth be told, as great as it was with Anna, I was ready to graduate and try out my new skills on girls my own age. It was a tearful good bye at our last lesson at the little apartment that I gotten to know so well. With a promise to come visit me one day in the US she gave me a kiss and a good bye blow job and we parted.
When I got home I had to repeat the 10th grade but that was fine with me, my public High School in the US was coed. With my new sexual confidence I had plenty of girlfriends and lots of sex. I had Anna to thank. Not that I was the best looking, or the biggest guy in school, nor did I possess great social skills, but I did have one skill. I knew my way around a woman’s body. I was maybe the only guy in the whole school who knew where to find a clitoris. I learned girls talk to each other about things like that. I fucked freshmen on up to even a senior. By my own senior year, older than almost every student in school, I make out like no ones business, it was like shooting fish in a barrel.
It was in my pussy filled senior year that I received a letter from Anna informing me she would be in New York soon and she would love to see me. By that time I had plenty sex in my life, but I thought it would be fun to see my tutor and wrote back sure I would love to get together for a drink and dinner.
When I met her in the city for dinner, boy was glad that I did, she was with a friend, a very attractive younger woman named Susan. Susan was in her early twenties, with fair skin and light brown hair, sort of a younger version of Anna except with, what I noticed right away, much bigger tits.
I learned that Anna had left her husband and was now tutoring for the other team; Susan was her new student. Susan knew all about me. She told me she preferred women over men but she found me cute. This was in the first fifteen minutes of meeting her. I knew I was in for a special night.
After dinner we where all back at their hotel room to getting to know each other better, much better. I didn’t know how to get a threesome going, but Anna of course took charge. She said to Susan:
“I’ll show you how I seduced this stud when he was still a young boy.”
And proceeded to reenact that first blow job of four years earlier. Only in mid-blow job she stopped and told Susan to come kneel next to her, she want to share this cock with her. Susan did as she was told. No longer a k**, I held off dropping my load on them both until much latter in the evening.
Anna was in her professor mode directing her two students in the art of pleasuring each other and her. Anna being the good educator that she was, had brought along study aids, such as a strap-on dildo. I dropped my first load of the night fucking Susan in the ass while she fucked Anna with the dildo.
They stayed a week, and what a week it was, after a day of sight seeing we would order dinner in their room, and then continue with our hands on sex education. It was hands and cock and mouths and pussy and asses, and tongues, in every combination possible and some I had never even thought possible.
It was just one more gift of the many that Anna had given me. So I bought her a nice pair of earrings before she went home. My experiences with her, almost thirty years ago, remain to this day the best sexual experiences of my life.