Jump to content

My comical adventures with the opposite sex

Recommended Posts

                                                                                 Pauline Phillips  




My first sexual boyhood experiences with the opposite sex took place at the age of twelve.

Let me relate what happened.

I went to boarding school as my parents were overseas my Father working for Burmah Oil Company. (That’s not spelt wrongly that’s how the company spells its name and they’re still in existence today.)

Anyway after tea we were confined to certain areas of the school. So as would be, rules are made for breaking especially when you’re twelve years old, so my friends and I decided to break bounds. We agreed to break out and head for the playing fields that were the other side of a main road. Vic Algernon (short for Victor) led the way followed by myself and Pete Buckhurst brought up the rear. When we got to the playing fields we headed for the hut, it was there at the side of the field up alongside an 8ft. hedge. Workmen who were doing some work in the surrounding fields, used the hut during their Tea Breaks. Now it was deserted and the three of us entered it, we were sitting there just chatting excited that we’d broken bounds when we saw Pauline Phillips walk past the hut window. We all jumped up opened the door and yelled for her to come in, which she did.

Pauline was a local village girl, well known by most of the older boys in school, as lots of stories were circulating about her. She was 16yrs old and had rather large breasts. Anyway we started chatting her up and soon the talk turned to sex. After allowing us to play with her tits and her crutch she took her panties off and lay on the hut floor. Soon all three of us had our pants off, Vic was the first to go, he lowered himself onto her, inserted his 3 inch dick and after about half a minute shot his load. I went next with a similar sized cock, and after sticking my dick inside her (this was the first time for any of us) a couple of strokes and I was shooting my load. Pete who had been waiting impatiently lowered himself down on her, but before he could get his dick inside her his hips started pumping and he shot his load all over her dress. God, was she bloody mad, it would leave a stain and she would have to go home like that. We took the piss out of Pete something wicked on the way back to school.


We entered the school grounds and didn’t see Pauline again till about 2 weeks later. We were in the workman’s hut again, and like the previous time she came by. She came into the hut and we started chatting and then we tried to feel her up again, but she resisted and told us not to do it. The three of us were all worked up so we didn’t take no for an answer. Pete grabbed her legs, and I wrapped my arms around her pinning her arms to her side, and Vic started to put his hand up her skirt to take her panties off.  She struggled so much that she got her legs loose and started kicking out, so we let go of her and got the hell out of there, and back to school.

The next day during lessons the whole school were taken out of their classes and assembled in the main hall, and up on stage was the Principal, Pauline, and her mother. The next thing was after being identified by Pauline Phillips, we three were pulled out of assembly and told to go to the Principal’s office and wait there for him.

About ten minutes later he arrived, and had three shit scared boys standing in front of him. Sitting down he looked at us and asked us, “Why did we try to rape Pauline Phillips.”

We were dumbfounded then shouted out, “We didn’t try to rape her sir, and because she wouldn’t do it with us we thought she was just trying to be awkward. So we tried to make her but because she struggled so much we gave up and left. We couldn’t understand why she wouldn’t do it like she did the last time.”

The Head stood up what do you mean the last time he asked.

I said, “The three of us did it to her about 2 weeks ago sir.” He had a bit of a smile on his face and asked, “What did you do to her?”  So Vic says “We put are thingy’s into her and shot so we didn’t know why she wouldn’t do it this time.”

“Didn’t you Idiots know that she was having her Periods”? He asked. We all looked at him with blank faces and Vic asked. “What’s Periods sir?

He looked at us,  “You’ll learn about periods at a later date, meantime you boys will go without pocket money for the rest of term, and if any of you are in front of me again I will inform your parents and expel you, is that understood.”  All three of us nodded he then dismissed us and we left his office.


Only six months later did I learn what periods were as did the other two. Meanwhile for the rest of the term the three of us had reputations that many of the other boys would have given their right testicle for.

I often wonder what Pauline Phillips thoughts were, on being screwed by Three boys in less than two minutes. Mind you she was good wank material for quite a few months till Valerie Caxton got her hands on me.






One of the first girls I ever went steady with was Valerie Caxton.

I’d been going out with Valerie for a couple of years from the age of thirteen, she used to live across the road from me. I, at that time lived with my aunt as my parents were overseas.

My aunt, was a friend of the Caxtons that’s how I got to know her. Valerie, took a liking to me she fancied my long hair and tan.

I was attending boarding school so only saw Valerie during the holidays. While I was at boarding school she used to write to me. I was one of the few boys who got letters from a girl-friend and I guess the youngest, which was a terrific status symbol, I used to feel ten feet tall but in reality was 4’ 11”.

Anyway, we used to see each other when I came home on holidays, and go to the movies, and such, no sex was involved at that time only friendship.

When I was nearing fifteen, we started having some heavy petting sessions, she would feel my dick by putting her hands in my pocket and I would finger her and play with her breasts. One day her parents were out, I was never the forceful type actually a bit shy, she dragged me up to her room, we started kissing and some heavy petting, when suddenly she said, “It’s about time we had sex.” I knew the basics about contraceptive’s and the like so I told her “I didn’t have any.” You wouldn’t believe it she pulled one out, (She must have been planning it) and from that day we started having sex on a regular basis.


About three or four months later, when talking about sex with some of my friends at school Vic included, one of the older boys tells me. “The best method is to get her to lie across the bed with her arse right on the edge, then lift her legs up in the air and then do it, you’ll be able to get your balls in as well”. So, being naïve, and armed with this knowledge, when I went home for my summer holidays, I intended at the first opportunity to try it out. About a week later when her parents were out, we headed up to her bedroom. She dropped her knickers, I my pants, put on the rubber then told her to lie across the bed. She looked a bit surprised but did what I asked, then when she’d got to the edge of the bed, with a bit of a struggle I lifted her legs into the air. I lined myself up, and leaned over to enter her.

Now comes the tricky part. Valerie’s bedroom floor is covered in Parkray tiles that are highly polished, and she had a bedside mat that I was standing on. So, as I leant over to enter her, the mat slipped from under my feet. I came crashing down, my face hitting her in the crutch.

My erection went down so fast it was ridiculous, and she was killing herself laughing, which only added to my embarrassment, jeez! I could have died. But we did succeed the next time with the bedside mat, and my socks removed, didn’t get my balls in.




This story about my adventures with the opposite sex was like a Shakespeare play, Loves Labour Lost.

I had left school at 16 yrs and 6months without the knowledge of my parents, as they were still overseas and started work as an Apprentice Electrical Engineer.

I had met a girl Una, just can’t remember her surname it might have been Daley but I’m not too sure. Anyway she happened to be a friend of Valerie’s so that was how I came to know her, picking up girls on my own at that age just about terrified me so I usually relied on friends.

Una was a prick tease, she would let me play with her breasts, and finger her and she wanked me a few times, but would never let me put my dick up her crutch. This particular day I came home from work and she phoned me, (I’d left my aunt’s house and was living with a cousin who had his own house, and had rented a bed-sit to me.) I spoke to her and told her to come over to my room as we could have more privacy.

She arrived about 6.30pm and after a brief hello, I started on her trying to get between her legs. After about an hour of really getting her worked up she conceded to letting me shag her. I was all excited then realised I didn’t have any rubbers, and that really annoyed me as she wouldn’t agree to doing it without one. So I started on her again, and by promising her that I would pull it out when I was going to discharge, got her to agree  to open her legs again. This time I had my pants off in two seconds flat, she was on her back and I buried my dick inside her without any ceremony. I started pumping and having been worked up for so long, it wasn’t going to be long before I achieved an orgasm.

Now at nearly 17 I think I weighed just over 8 stone about 120lbs. So being buried deep within her and nearing my orgasm, there was no way I was going to pull out. Una sensed this, and just as I was about to blast off, she had her hands on either side of my pelvis and she just lifted me up and threw me off her. Bloody hell, one minute I was deep inside her fucking like a madman, the next I was flipped off, her furiously fucking fresh air and my spunk flying all over the place. Boy was she mad at me, as some of my semen had gone on her clothes and for not pulling out like I said I would. For me it was terrible not having anything wrapped around my dick when I was cumming and ending up on the floor. Needless to say the next time I made sure that I had an ample supply of rubbers.

So now you know why I call it Loves Labour Lost.


In conclusion what I did learn about the opposite sex, was that they cannot handle the male organ as proficiently as another male. Females are competent, but men, from a very early age learn how to play with their ding-a-ling. So woman are a lot less experienced and not in the same class as a man.

My adventures with the opposite sex came to an end, when I met a rather handsome boy during my Engineering apprenticeship. Who seduced me, and gave me the best hand job of my life. He’s kept up the good work ever since, and the best part no rubbers involved.

Link to comment

Create an account or sign in to comment

You need to be a member in order to leave a comment

Create an account

Sign up for a new account in our community. It's easy!

Register a new account

Sign in

Already have an account? Sign in here.

Sign In Now
  • Create New...