Rip

foreskin

David Trenchant carried his virginity like a millstone. The swinging sixties and sexual liberation were long ago and, at eighteen year of age, he felt cheated. His mates boasted of regular sexual encounters, though they were conspicuously short on detail. Meanwhile, all the women of his age that he knew gave the impression that they were virgins. Something didn’t add up.
His ex-girlfriends had been a big disappointment. Only Jennifer had even permitted him to play with her breasts and that was the absolute limit she set on their intimacy.
Sally was David’s latest girlfriend of three months and, at long last, matters sexual seemed to be on the up. David really liked Sally. She was pretty and sensible; displayed little of the childish regression that his previous girls had hidden behind. He genuinely enjoyed Sally’s company and conversation but, most of all, he lusted after her body.
Sally had initiated French kissing on their second date. He was thrilled and encouraged by this show of independence and reciprocated desire. David felt that Sally would take him all the way, provided he let her set the pace. So he suppressed his urges and went with the flow.
After four weeks, their meetings settled into a pattern: they were together at her parents’ house most evenings, usually kicking around in the lounge or kitchen. But every Saturday night, her parents went to the local pub from eight to eleven, and Sally wasted no time in leading him to her bedroom.
He liked the way she gave him clear instruction as to which parts of her were on or off limits by guiding his hands, groaning with pleasure at his touch, but tapping his wrist if he wandered too far, as they kissed. Most of all he liked the way the on limit grew a little larger every Saturday night.
By Bonfire Night, they were both naked except for their knickers. Genitals were still out of bounds but David felt things were moving apace and it was only a matter of time. On the second Saturday of December he decided, albeit with some trepidation, to try using Sally’s tactic, took her right hand from behind his neck and guided into his knickers. He expected resistance or, at the very least, some reciprocal trepidation on Sally’s part. Instead she eagerly sought out his erection, began to massage gently whilst purring in his ear, as though she had been waiting for the invitation. David was so bowled over by this affirmation from Sally that he was moved to tears.
The following Saturday, David could sense the impatience and expectation in the air as they waited for Sally’s parents to get ready and leave. The very moment the door clicked shut behind them, they dashed up the stairs, giggling with excitement and tearing off clothing on route. David was slightly alarmed when Sally pushed him back on her bed, leapt on top of him, her hand immediately seeking his cock as she snogged him hungrily. Still she would not permit his hand inside her knickers but grunted and panted as he fiddled with her clit through the sodden cotton.
The fourth Saturday was Christmas Eve and her parents stayed in. David couldn’t cope with being with Sally yet unable to play with her, so he went home early. They met again on Christmas day to exchange presents. As they parted, Sally whispered in David’s ear “They’re going out tomorrow afternoon”.
Her parents had already left when she opened the door to him.
“Hello” he said.
“Fuck hello” she barked “get upstairs and get your knickers off!”
He obeyed at a gallop. This time, she too was naked as she jumped on top of him. Is today the day he wondered. But no, their activities were much the same as nine days previously, albeit with the added excitement of full nudity. He enjoyed what they did together and felt closer to Sally than ever before but still worried that she held so much in reserve and winced when he thought he still carried the label “virgin”. She recognised that he was brooding as they parted.
“You want to go all the way, don’t you?” she asked as she was dressing.
He was surprised at the question, first because of her directness but also because he thought the answer was obvious.
“Oh, yes Sally” he pleaded.
“Mum and Dad are going to a party on New Year’s Eve. We’ll do it then.”
“God, yes, do you mean it? Don’t tease me. Are you serious?”
“Yes, it’s time. I want you.”
The next five days dragged interminably. David could not think of anything else but their planned sexual encounter. His excitement was palpable but also he was fearful. Could he perform to Sally’s satisfaction? Her confidence scared him. Was she really a virgin?
New Year’s Eve found David in a state of acute agitation and near exhaustion. He’d spent the previous day and all night worrying about Sally and whether he would measure up to her expectations. He’d had no sleep and felt like he had a cold coming on. He spent the day trying to find something to distract him but nothing seemed to help. By the time he presented himself at Sally’s house at eight-thirty, he looked like death warmed over.
“God, what happened to you?” was Sally’s greeting.
“I’m just a bit tired” he replied.
“Do you still want to do it?”
“Yes, of course I do” he lied.
“Look, it’s no big deal. If you’re not feeling up to it, we can take it easy and try another time.”
“No, I really want you. Please don’t make me wait.”
“O.K. come on then.”
They stripped, she pushed him back onto her bed and they started kissing and heavy petting, as before. David started to relax a little and enjoy the stimulation.
Sally broke off kissing and panted into his ear “I’ll go on top the first time”.
She straddled his hips and guided his penis to her vulva as she sat back. He felt her warm and wet against his throbbing penis. This is it he thought and his every muscle stiffened involuntarily in anticipation. He was trembling with excitement. She still held his shaft tightly in her hand and started to rock back and forth. He expected to slide into her but instead he felt his cock being crushed, harder and harder as she pushed down upon him. Sally grimaced with pain but kept to her task, pressing down harder whilst manoeuvring his cock with her hand. Still he felt he was not inside her and, worse still, because of the mauling his penis was taking, thought he could not avoid orgasm for much longer. Then, in an instant, he was inside her and coming, but also squealing and writhing in agony. Sally climbed off him and turned to inspect the damage. David’s frenulum, the tie between foreskin and glans (bell-end) had ripped open and was oozing blood into the stream of semen flowing from the tip. David sobbed.

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3 responses to “Rip

  1. This is a very interesting story about first time and virginity. The shame of being a virgin at a certain age and the first experience… that should be a real first experience, not just a random experience.

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