I was taught to masturbate at the age of 12 by a very sexy but frustrated older lady (see 'Thank you Aunty Doreen''). In the months after this I started to masturbate virtually evey day, often twice and sometimes more. By 14 I considered myself a connoisseur. My favourite method at the time was humping my pillow while fantasizing that I was really fucking a girl. But I was still so shy that I couldn't even talk to girls, other than a couple I had sat next to in junior school (age seven to eleven in the UK) and then only to acknowledge them. Our senior school (11 to 16) was sex-segregated; all my male friends would openly boast about and discuss their masturbation exploits and techniques, but I kept mine strictly to myself. About this time a group of my friends started having wanking contests, seeing who could cum quickest, shoot furthest etc. I longed to join in, but was too embarrassed. After a while a couple of girls joined in this group, including to my surprise, Caroline, one of the girls from my junior school that I acknowledged. She was a pleasant, petite girl with a rosy complexion and short, raven hair.
One afternoon after school when I was round at my friend Paul's house and he was upstairs changing, there was a knock at the door. I peered out from behind the curtains and saw it was the wanking contest group, with two girls, including Caroline, all laughing and joking. I didn't really know the other girl, except that she was nicknamed Mounds, because of her very large breasts.
I froze. When Paul came down he answered the door and there was a hushed conversation. After they had gone he asked why I hadn't answered the door. I flushed and tried to change the subject. He said there was a meeting at Caroline's the next day, as her parents were out and that I should come along and have some fun. All that night and the next day my mind was in turmoil. At the end of school Paul said to me 'If you want to come be at my house by 4.30. and have a wank before you come.' As I went home I must have changed my mind a dozen times, but at 4.30 I was on Paul's doorstep with a dry mouth, my stomach in a knot and a raging hard on. We walked in silence to Caroline's house and when we arrived two of our classmates were already there. They teased me mercilessly, but Caroline quietened them, gave me a hug and told me 'You'll be fine.'
'As it's AJ's first time I'll go through the rules,' Caroline announced, producing a battered old school exercise book and opening it to a page ruled into columns. 'Your initials go here' she said filling them in. 'And the size of your knob goes there and ... oh, you'll soon see. But there's no fucking and there is only one boy allowed in at a time and there must be two girls. Alright. Who's first. AJ?.' I backed towards the door, but she grabbed my arm, 'No AJ. Please stay.' 'Paul, how about you?.' There was a spark of anticipation in the air and all the boys had prominent bulges in their trousers.
Paul followed Caroline into the bedroom with a sheepish grin on his face, and they were joined by Mounds who locked the door after them. All was quiet for a while and then the girls started to giggle. This was followed by another, longer period of quiet, more activity and the girls cheering. Paul came out smiling and tucking in his shirt. 'Paul did really well today' said Caroline, following him. 'At least better than last week' added the normally reticent Mounds, and both girls collapsed in laughter.
'I think we'll have Nicholas next' said Caroline, recovering. Nicholas had easily the biggest prick in our year. He was regularly teased about it in the showers, but everybody really envied him, myself included. There was a rumour that he was 'queer' ('gay' just meant happy in those days) after all he had been caught fondling his neighbour in a maths lesson. But he certainly seemed keen on some female attention today. A similar succession of activity and quiet periods followed from the locked room, climaxed by Caroline screeching 'Wow!'. Nicholas emerged still wearing his school shirt and tie done up, with his trousers over his arm and his still semi-erect, meaty penis sticking straight out in front of him.
Caroline approached me, took me by the hand and led me into the bedroom without a word. I was shaking and my erection had vanished. 'We need to measure your knob first,' she said 'so take your trousers off.' I did as she said. 'I think AJ needs a little help' she added grinning at Mounds. Both girls were still in their green and white check gingham school dresses. Simultaneously they both slowly unbuttoned their dresses to the waist and slipped their arms out. Caroline was wearing a pink, soft cotton bra with white lace trim around the straps, not much more than a short vest really. She pulled it up and her small perky breasts popped out, revealing what would now be called 'puffy' nipples, of the deepest pink. Mounds had on a plain white bra, which she quietly unfastened and let fall to the ground. Her nickname was certainly well earned. Her breasts were full, firm and round, and when she released them they hardly moved. Her nipples were browner and longer than Caroline's but with smaller, smooth areolae. She tweaked them with her finger tips, then gently squeezed them and they responded instantly, becoming invitingly erect. My own erection returned, pulsing visibly as strained to it's maximum. The girls giggled again. 'That's more like it!' observed Caroline, tape measure in hand. 'Ur, five and a half inches' she called out and Mounds entered it into the battered exercise book.
'Now Mounds is going to wank you and you've got to last as long as possible without coming, OK?' Now I saw why Paul had told me to wank before I came out and I was starting to wish I'd taken his advice. Mounds knelt in front of me and grasped my penis, whilst Caroline looked at her watch and counted down 'Three, two, one-go!'. I tried not to look at Mound's gorgeous, heaving breast as she almost mechanically slid her hand up and down my shaft, making my cap bulge and tightening my frenulem. But when I looked up I saw Caroline gently playing with her nipples as she counted out time. It was obvious that they were deliberately trying to foil my attempts at holding on. Mounds increased her pace and pressure, wanking me frantically. 'Come on,' she said 'come on, do it, squirt, squirt!' And try as I might I just couldn't hold out any longer. I gasped to orgasm and my knees buckled as I shot a powerful jet of cream, hitting Caroline who was standing several feet away behind Mounds. She clapped her hands in delight. 'Goood boy' agreed Mounds.
'You get a rest now' said Caroline, and she joined Mounds in a huddle in the corner, where they remained for several minutes in deep conversation. When she emerged from this scrum she told me 'This time you've got to cum as quickly as you can.' They had both slipped the tops of their dresses back on, but they were still unbuttoned and as they moved around the room I could still catch tantalising glimpses of their breasts and nipples. I was starting to get erect again already when Caroline lifted Mound's skirt above her waist, revealing her regulation navy blue school knickers. Mounds pulled these down around her knees 'Isn't it funny,' she said 'that your arms are just the right length to reach your fanny. Your hands just sort of go there don't they.' She gently squeezed her downy lips together and then released them. 'Ready AJ?' she asked. I was rampant.
'It's my turn now' said Caroline and she knelt down at my feet. I was expecting another pounding like Mounds had dispensed to me. But as Mounds gave the command to go, I felt Caroline's tiny delicate hands start to explore and caress my throbbing penis. She tickled my frenulem, opened my slit with her fingertips, stroked around my cap, gently massaging the flare of its ridge. This was heaven. Half of me wanted it to go on all day while the other half wanted to shoot the biggest load of my life there and then. God, these girls knew what they were doing, mind you they were getting plenty of practice! I started to thrust with my hips to increase the pressure. 'Hold on,' Mounds called 'calm down, slowly, enjoy it. Hold on, go with it.' But I was desperate now, it seemed that Caroline had been teasing my prick for hours. I was sweating, groaning out loud 'Oh please let me cum! Please!.' But Caroline just eased back the pressure and slowed down the pace, barely touching me now. Occasionally she would pluck my frenulem or run her little finger around my ridge. Then as she did this her dress fell open and I saw those perky, pink, puffy nipples pointing up at me. That was it, I went over the edge and as soon as Caroline realised she obligingly wanked me long and hard. I shot pulse after pulse of thick cream over her, in her hair and on her hand. 'Oh yes,' she said 'that was fab!'. While I recovered on the bed, she cleaned herself up and Mounds came up and gave me a cuddle,'Well done' she added 'I think you enjoyed that didn't you.' I went to join the others and the last boy, whose name escapes me after so long, went in. I was in a daze and slumped in a chair. Paul asked how it was. All I could say was 'I think I've got over my shyness of girls.'