Chapter 3
Virgin no more
My relationship with Charlotte meant that I maintained an active sex life but my virginity was still intact. Masturbating Philippe and sucking off Serge remained my only experiences involving men, or rather boys. But given my natural curiosity about what it would be like to have sex with a man, it was only a question of time when I would try it out.
Ironically, it was my virginity which delayed my first encounter of the penetration kind. I knew that losing my virginity would be an irreversible, once-in-a-lifetime, never to be repeated experience. I didn't want it to happen casually or even accidentally, it had to be a special occasion, a memorable event. So whenever a situation arose where I asked myself 'would I want do let this guy take my virginity?', the answer was inevitably no, and in spite of some really valiant efforts at seducing me, I never let it go beyond kissing and petting - some of it quite heavy, with hardly a piece of clothing left in place.
One Sunday, Charlotte invited me for lunch at her place. "Don't expect me to spend hours in the kitchen, though," she said, "I'll buy some ready dishes from the delicatessen and add my personal touch." She also put some wine into her fridge to chill.
We enjoyed the food and wine and each other tremendously. At one point, Charlotte, lying in the easy chair with her legs up in the air, decided to pour some wine into her slit and made me drink her 'pussy wine' as she called it. Of course, I didn't stop there. Later we changed roles and I served as her chalice.
It was a glorious spring day, too beautiful to stay indoors all the time. So we decided to go for a stroll in the nearby park. We were both slightly tipsy from the wine we had consumed and Charlotte was in an exceptionally good mood, so good that I felt comfortable enough to bring up a subject which she was normally not keen on: my defloration. We were sitting on a park bench, a little off the main path, sheltered from the general view by a hedge. I started off by telling her that I thought the time had come for me to lose my virginity.
"Anyone I know?" she asked casually.
"No, I didn't have anyone particular in mind. You know I don't have any male friends, and I don't really feel I want to get involved at this stage."
"In that case, how did you intend to go about it? Put an ad in a newspaper? Donate it to charity? Sell it to the highest bidder? Would you consider a gang bang? That way the question who was the first becomes almost irrelevant."
"Well, not exactly sell it to the highest bidder, but I thought I could let the most suitable man do it."
Charlotte was intrigued by the idea and saw a possibility for an experiment in human behaviour. "Define suitable," she said.
"It would have to be someone who can do the job well, you know, be gentle and give me some pleasure in the process."
"Hmm, that's an interesting idea, but you can't ask for references, like the names of other satisfied girls they have already deflowered. And you can't let them do a dry run and select the most suitable one based on the results. I suppose, it would have to be a best guess selection from the small group of boys you know."
As I thought about the boys I knew who might be worth considering, she peeked against the sun along the path where a group of three figures was coming towards us and said, "Well, speak of the devil."
It took me a while to realise that one of the three was Serge. The other two figures were boys roughly his age. They slowed down for a moment while Serge said something to the others, then they approached us.
"Hi Jacqueline, are you still wearing those woolly knickers?" Serge said, provoking laughter from the other two. I could have killed him for this stupid remark and decided to ignore him.
"As it happens, she isn't wearing any knickers at the moment. If you care to sit down over there, you can check it out."
Charlotte had decided once again to humiliate me. The three boys walked to the place which Charlotte had indicated and sat down on the grass. Charlotte leaned over to me and told me to spread my legs. Then she lifted the hem of my skirt so that the three boys could have a view of my pussy.
"This is your chance," she said while she slipped one hand into my blouse and started playing with my nipples. "I bet, all three are able and willing, you just have to chose one. Which one do you like best?"
I told her that I wanted to select my first male partner based on objective criteria, rather than good looks, a nice smile or pleasant manners. After all, these things did not guarantee that a boy was up to the task in question. She asked me what these objective criteria were and I said, "Well, he's got to turn me on, he's got to make it a memorable experience."
"That's not very objective, my dear, and whether it's been a memorable experience is something you'll only know after the fact, not before."
Charlotte did not seem to take my idea of selecting the most suitable candidate very seriously - in fact she thought the whole idea of selecting the man who would make a woman out of me based on objective criteria was hilarious and at one point she suggested to make them draw lots - but in the end we agreed on four criteria. Each boy would have to French-kiss me, caress my breasts and stroke my pussy and I would award points for the stimulating effect they achieved. This score would indicate whether the candidate would be able to make this important step in my life a pleasurable one. The fourth criterion was the size of his member, which we also considered relevant.
Charlotte pointed out that if I was serious about not being influenced by good looks, a nice smile, etc., then it would have to be a blind test, in other words I shouldn't be able to see the candidate who was stimulating me. I found that suggestion very weird, but I had to admit that it was the logical consequence of my own idea.
While we were talking, Charlotte had unbuttoned the top of my blouse and continued to play with my nipples. I started to get excited and slid down on the bench so that I was now in an almost horizontal position with my legs spread wide to offer the boys the best possible view of my pussy.
The three hadn't moved from their spot. They kept looking in my direction and enjoyed the improving view of my pussy from the distance. I could hear them talk and laugh, but couldn't make out what they were saying. Charlotte announced that she was going to inform them of our plan.
As she got up from the bench and walked over to the group, I assumed a slightly more respectable position. She addressed the three as 'young gentlemen' and explained that she was proposing a 'somewhat unusual competition' and that the winner would be able to a collect a 'unique and precious reward'.
I had mixed feelings hearing her talk like that about me, but had to admit that she was only presenting my own idea. After all, it had been me who started the conversation about me losing my virginity. As the boys wanted to know more about this competition, I heard her talk about the beautiful spring day, the sap rising and the birds and bees.
As she spoke, the wind picked up a little and it became increasingly difficult for me to hear what she was saying. I watched them talk and occasionally laugh, but could only understand the occasional word. I heard one of them say 'completely naked' and saw Charlotte nod in agreement. Then Charlotte said something which included the word 'condom' and all three of them pulled a brand new packet from their pockets. In the end Charlotte shook hands with each of them as to seal an agreement; then she returned to our bench.
Charlotte pulled me up from the park bench. "It's all agreed. Let's go. We need to prepare a few things before they come."
On the way she told me that they had agreed to my selection criteria, that they had insisted I be completely naked throughout the competition - and she didn't think that would be any problem for me - and that the lucky winner would use a condom. They had also demanded that the winner be able to enjoy his prize in privacy. This meant that she and the two losers would have to leave as soon as I announced the winner.
Charlotte considered her bedroom a special place and she wasn't going to let a bunch of boys defile its sanctity by deflowering a virgin friend of hers in it. Therefore we carried her bed into the living room and drew the curtains to keep prying eyes out. Charlotte also suggested I had a little more wine to calm my nerves. I followed her suggestion although I felt that it was really her nerves which needed calming. When the doorbell rang, she told me to strip and lie on the bed.
As the three boys entered the room and inspected my nakedness, I felt like a whore who was receiving prospective customers. On the other hand, I wanted them to be turned on so I displayed myself in a very sensual pose. Charlotte ordered the three candidates to remove all their clothes and soon they stood there, naked, their erections swaying in the air. There wasn't any significant difference in the size and shape of their cocks, so this probably wouldn't be the deciding criterion.
Charlotte told me to have a good look at my pretenders because this would be the last time I'd see them. Then she blindfolded me and proceeded to have the boys draw lots to decide who would be first, second and third. She reminded them to remain quiet because otherwise I might be able to recognize from their voices who was Number One, Two and Three.
Soon Number One approached the bed and kissed and caressed me. I couldn't help finding the situation very weird. There were three naked boys queuing up to convince me that they were the best choice for my first ever fuck. And in order to convince me they performed a sequence of pre-defined activities for which I awarded marks. Wouldn't it be more natural to let them all get a piece of the action?
My mind was still on these thoughts when Charlotte told me I still had to evaluate Number One's penis. I didn't just want to take it into my hand, I wanted to see it and took off my blindfold.
Charlotte jumped on me like a tiger to put the blindfold back, but she came too late. I had already seen the penis - and the boy it belonged to. She scolded me for having spoilt the experiment. She would now have to assign the candidates new numbers and start again from the beginning. And, to avoid a repetition of what had just happened, I would have my hands tied to the bed. After Charlotte had found some suitable pieces of string and tied me up the competition started anew.
The way I was lying there - naked, blindfolded and my hands tied to the bedposts - must have really turned the boys on. Or maybe I felt aroused by my own vulnerability. Whatever the cause, their kisses and caresses did have a stimulating effect on me and my excitement rose with each candidate. On reflection, I would say today that, scientifically speaking, my experiment was seriously flawed, because each candidate benefited from the level of excitement the previous candidates had achieved. So Number Two achieved a higher score than Number One and Number Three scored even higher and was declared the winner.
Charlotte told the other two candidates to get dressed and leave. I heard some grumbling; they were obviously not pleased about losing. Then Charlotte gave me a kiss, wished me luck and told me to enjoy myself. She would be back as soon as it was over.
My heart was beating fast in a mixture of fear and anticipation of things to come. Soon after the door closed I could sense the weight of another body on the bed and a few moments later that weight was on top of me. A hand pried between my legs, searching for the entrance and then guiding an erect penis into my vagina. My suitor apparently thought there had been enough foreplay already and decided to come straight to the point. He also didn't find it necessary to untie my hands or remove my blindfold. He pushed a little further inside me without any difficulties but then hit some resistance. As his cock forced its way through, I felt a short, sharp pain and had the sensation that there was some bleeding.
Once this obstacle was overcome, he started pushing in and out of me, at first slowly, but soon getting faster and faster. His breathing became louder and faster and soon his body trembled and he came. Very soon after that, he withdrew his softening cock from me and got up from the bed. I could hear some sounds, probably of him getting dressed, then the door opened and just before closing it again, he said, "Thank you."
There was complete silence. I was lying on the bed, blindfolded and with my hands tied, wondering if this was all intercourse amounted to. It had been over so quickly, I didn't really have a chance to decide whether I liked the sensation of having a penis in my vagina. It hadn't caused me any great discomfort, but there hadn't been much pleasure either. I concluded that this particular male probably wasn't very experienced - it was quite possible that I had been his first ever woman - and that it would be much better with an experienced man.
When Charlotte returned and helped me get up from the bed and wash myself, she was full of scorn for the fool who didn't even have enough sense to untie me and remove my blindfold. "You weren't supposed to see them before the decision, but there would have been no harm in you seeing the winner."
The episode confirmed her long-held conviction that males were completely useless, particularly when it came to satisfying a woman's needs.
In case there are any virgins out there reading my story, let me give you this advice: Very few men still consider an intact hymen a certificate of quality and expect their brides-to-be or girlfriends to be virgins. Nobody is going to return you to your parents as 'damaged goods' if it turns out on the wedding night that you're no longer a virgin. The hypocrisy of demanding that girls remain 'pure' while boys are expected to 'get some experience' has become too obvious.
Getting your hymen out of the way is not a pleasurable act. But it clears the path for fun and fulfilment. The problem is that most people consider defloration and first intercourse one and the same thing, or as two things which are intrinsically intertwined. They are not!
It's like the opening ceremony for a new bridge or a new stretch of railway track. During the ceremony the official only cuts the ribbon. The real traffic crosses the bridge some time later. Nobody uses an actual train to burst through the ribbon, they use scissors. The first train comes when the ceremony is over. Likewise you should plan the clearing of your entrance as a separate step so that you can later surrender to your chosen partner without any fear or anxiety.
My advice to all virgins is: do it yourself, in a quiet moment. Or ask your best friend to do it for you, using a candle, a carrot, or whatever other implement you prefer. If you really feel it's something that merits a big celebration, invite a few friends 'round for an inauguration party. You can even have the one who does it announce, "I herewith declare the pussy of (insert your name here) open to public traffic."
However, if you're one of those girls who already have a long standing relationship and want that man to be the first and only one - and I say this without a sneer - maybe you want to give your chosen one the honour of making a woman out of you. In that case, yes, let him do it, as long as both of you understand that this isn't sex, but merely part of feminine hygiene - and it's not likely to be a memorable event.