Written by wildchildtammy

05 Oct 2013

my first sexual experience with a man

Many of the guys (and some girls!) have asked me how and when I first had sex.

It’s not the way I would recommend to any girl now, but, like so many things when one is young, it seemed like a good idea at the time!

I was born and grew up in Cape Town, where my father still lives. I went to an all-girls school in the suburb of Rondebosch. I guess it was a typical girl’s school- lots of good times and good friends and a lot of real bitches, practising for marriage and making their husbands unhappy.

By standard 8 (grade 10 in JHB), I was 15, and already quite well-developed. Some girls at that age are still like boys- no hips, no shape and maybe small boobies, but I was more like a small woman. I had nice hips and legs, a very nice bum, and quite large boobs. (Not little cones, but more full and round.)

From when my boobs started to develop beyond just bumps, I could see the effect they had on the boys. When I went up stairs, boys would try to be underneath to see up my skirt, and at the beach boys would stare at my boobs like only a 15-year-old can.

In gym, some of the girls had shaved legs, but most left their pussy-hair as it was, with maybe a trim on the sides so they could wear a bikini.

I had seen my older sister and her friends nude a lot, and I knew what pussy-hair should look like, so very early on I would shave it into a proper bikini shape, and even into a landing strip, which got a lot of bitchy comment from some girls: “she’s having sex, she’s a tart, she’s sleeping with the whole rugby team of the boys school” etc. but I liked the look and feel so I left it like that.

Anyway, back to first sex.

I had lots of boyfriends, although none very serious, and I had let a few of them go quite far when making out.

I had let them touch my boobs under my bra, eventually took my bra off and let them play with my nipples, feel my pussy over my panties, and I had felt their cock in their pants, and one guy I had let him take his cock out and I had stroked it . (The fact that he came at once all over me had a lot to do with what happened next! Have u ever tried to get cum out of a skirt? I am not sure what is in it, but it is the most effective stain ever- it NEVER comes out!)

I knew that I wanted to experience sex, and that I was emotionally ready for it, but I was not going to let any one of the guys I knew be the first, so that he could go around boasting that he had fucked Tammy !!

I had to find someone who knew what to do and do it well, and would keep quiet. Someone who had more to lose than I did by speaking out. Like?? A TEACHER!!

I had 2 very good friends who I could trust, so one night I told them of my plan, and we sat in my room going through the list of possible teachers. Well, we were hysterical- most of them we could not imagine naked, let alone fucking and some we doubted had in fact ever fucked. Some of the gay female teachers were considered, but I wanted a guy, not a girl- if we wanted to experiment with each other we could, we did not need a teacher to show us. (And we did later that year, but more about that later)

Eventually we narrowed it down to 2 teachers: a very good-looking guy, about 40, who took us for English, and the Art teacher, a guy about 30, who looked a bit like Hugh Grant- not butch and rugger-bugger, but softer and more gentle.

We decided that the English teacher was too old, and he was married, but the Art teacher was younger and single. So, Andrew (not his real name- don’t worry Sir, I won’t give our secret away!! although if u are on this site let me know- maybe I could teach you what I now know! Just tell me my pet name for your cock- then I will know its you!)

We figured out that we would need to get him interested before actually getting him to have sex, so I made sure that I was where he could see lots of me every Art class.

I would sit in the front row, and let my legs open a bit, with my skirt pulled up a little. From where he sat at his desk, I knew he could see up my skirt and see my panties (my friends and I had tried it, so we knew he could!)

At first he tried to ignore it, but one afternoon when I saw, out of the corner of my eye that he was looking, I quickly looked at him, and caught him looking. He went very red, but I smiled and opened my legs some more, and pulled my skirt back some more- bingo! he realised that it was deliberate . From that day on I would let him see more and more, both of my panties and, when he walked around to check on our work, I would unbutton one button of my blouse buttons and lean well forward, so he could see my boobs in my bra.

I don’t know what he thought was going to happen, but he seemed quite happy to look without trying to do anything else, so it was going to be up to me.

One afternoon, on a Wednesday, we had PT (PE, Gym, don’t know what it’s called now??) as our last period, and we were allowed to keep our gym clothes on if we had after-school classes. Which I did. ART!

The after- school Art class was in the school hall, not in the classroom, as we used lots of messy materials like glue and paper-mache etc.

The class went fine. I again made sure that I was in front, but now I was ready. I had shaved my pussy fully (although I did not have much hair there, then or now), and I had changed after PT into very small lacy briefs, not the regulation school blue granny-panties, and I had on a light-weight bra not the school version

When he sat in front, and I opened my legs a bit and he saw my pussy covered by the lacy panties, with a clear camel-toe, he almost fell off his chair! He looked carefully at me, and I smiled sweetly and stretched my hands over my head- it was sooo hot in there!! lol. my light bra hid nothing, and I knew he could see my boobs as though I was nude, and my nipples were obviously erect underneath.

Now the fish was on the hook. I waited till class ended, and then stayed to help him clear up. I think he knew what was possible, but could not believe it.

We packed away, and I opened the door to the store-room, where all the gym mats were stored. Once I had the key on the inside, I called to him to help with some equipment. He came over, walked into the store room, and I closed the door and locked it!

I went up to him, put my arms around his neck, and kissed him. Now I am a very good kisser, and when I kiss someone, they know they have been kissed! He tried to pull away at first, but I was expecting that and I held on behind his neck.

When he stopped pulling away, I took one hand away, took his one hand and put it onto my boob. My little nipple was rock-hard. Initially he did not move his hand, but then he started to fondle my nipple. I took his other hand and put it on my other boob, still kissing him.

I reached down and lightly stroked over the front of his pants- he was not fully erect, but he was getting there!

I was not sure what to do next. I had never given a guy a blow-job, so it did not occur to me to start there. I thought if he felt my pussy, he may carry on on his own, so I took his one hand off my boob and put it under my skirt on my panties. He slid his finger along my slit, and then , (and I guess it was at that point that he decided) he moved the panty fabric aside and slid his finger along my smooth (and wet) slit.

I unbuttoned my blouse and took it off, and then with his finger still on my slit, I took my bra off.

I knew from experience with boys that my boobs got attention, and his reaction to the sight of my young and very firm, full boobs suddenly in front of his face was amazing. He stopped all pretence of not wanting this, and started making love to me properly.

He leaned forward and kissed my boobs, my nipples and under my boobs. I was in heaven - he was so much better than the fumbling boys. All the while he slid his fingers up and down my pussy, slowly parting the lips and letting his finger go into my pussy.

I backed away, stepped out of my skirt, took of my panties and lay down on a mat. He looked at my lying there, and took off his shirt, shoes and socks and then his pants. He stood there in his boxers, and I could see what was for me then the biggest cock I had ever seen (by now, I know it was normal, but with only young boys to compare it to, it seemed huge)

I think he realised that if he took off his boxers while standing over me it would frighten me, so he lay down beside me, and put my hand on his cock. I stroked it like I had with the boys, but there was so much of it!

He put one finger into me, and pushed it deeper. I took his hand and pushed it even deeper, as my sisters dildo had gone in at least that far, and often.

He wriggled out of his boxers and I saw for the first time a fully erect, real-life mans cock.

He put my hand on it and I curled my fingers around the shaft and moved up and down.

Meanwhile, his fingers were doing their job on my pussy- I was really wet, and when he stroked near my clit I just moaned and arched my back.

We played like that for a while, me getting wetter and he getting harder, if that was possible.

Then he knelt over me, with his cock just over my wet pussy, and, playing with my boobs, asked whether I really wanted to do this.

I did not answer, but just took his cock in my hands, guided it to my pussy lips and opened my legs some more.

He asked whether I had done this before, and I said no.” it will hurt a bit”, he said. I told him I knew that and it was ok, also I was on the pill so he could do it.

He pushed his cock slowly into me, further and further, and I felt the most fantastic sensation inside me. He went deeper and deeper, and suddenly I could feel him up against my hymen. He paused, looked at me and I nodded. He gave one harder push, it hurt briefly, and then it was over- I was no longer a virgin!

He thrust more and more, and I got more and more excited. Suddenly I felt the familiar feeling of a climax approaching- I lifted my hips to meet his thrusts, and with a small scream came for the first time with a man inside me.

As soon as had finished cumming, I stopped him. He looked at me in surprise, but I said to him I wanted him to show me more before he came.

We chatted a bit, and I told him that I wanted him to teach me what a man likes, and how to do it.

The next diary entry I will tell you about what he taught me.