I wouldn’t describe myself as square exactly, but I was not the most world-wise 19 year old. I lived at home with my Dad and spent more time studying than getting up to regular sorts of teenage mischief.
I was still a virgin. I’d had some limited experience of sexual practices but never more than a series of fumbles with girls who were as shy and inexperienced as me.
When I started hanging out with Rebecca and Todd however, all that started to change. My name is Henry, by the way.
You know how it is at high school. There is always a group of ‘cool’ kids in the year who form a group. They tend to be the best looking, wear the trendiest clothes, have their own cars before everyone else and have a reputation for the wildest parties.
Well, Rebecca Ashton was one of this group at my school, Beaumont High. She was absolutely gorgeous which helped make her a magnet to girls and boys alike, but she was also a rebel which gave her the reputation of being cool too. She would come in to class late, openly challenge the authority of teachers and was one of the first girls in the year to be reputed to have “gone all the way” with her boyfriend Todd Bateman.
Todd can perhaps best be described as the male equivalent of Rebecca -good looking, popular, physically more mature than most of his friends and with a reputation for being a party animal. To be friends with Todd (if you were a guy) meant you were elevated to elite status by your fellow students. If you were a girl and you were lucky enough to date him, you would be the envy of the class.
Given their status as the rebel king and queen of the year, it was perhaps inevitable that Todd and Rebecca would end up an item. Their relationship was a pretty volatile one – they would just as likely be seen having a blazing row in the hall as they would making out in the schoolyard. But this was characteristic of their obsessive personalities and the fact that they were crazy about each other.
I couldn’t believe my luck when I first started to hang around with Todd and Rebecca and the rest of their group. I felt like I had been plucked from anonymous obscurity and finally given an identity. All of a sudden people knew my name and would greet me in the hallway; they would show me respect and laugh at my jokes.
I only became friends with Todd and his group by accident and to be honest, I never really felt I belonged. I tended to be the quiet one whenever we sat around our regular table at the diner, or the one who hovered nervously in the background while Todd and the other guys carried out some wild act or another.
They let me into their group only after I got my Dad to fix Todd’s car one afternoon (my Dad is a mechanic). He didn’t charge Todd anything for the repair and this was enough for me to start being invited to sit at their table in the canteen, and hang out with them on the weekends.
I never felt truly comfortable with them as a group of friends – they always seemed to be bitching about someone or other, or carrying out some action that undermined another kid in the year – but if truth be told, I did feel a lot ‘cooler’ than I ever had done before.
And I certainly had my eyes opened by them to a few things when it came to sex. There was one time in particular, which is what I want to tell you about here.
It was a Friday night and Todd and his gang would often spend Fridays at a bar called Mitzy’s. Mitzy’s is a dark, sleazy place where they played live music on the weekends. Todd and his gang had a favorite table against the back wall with a couple of benches on either side. At a tight squeeze you could get about eight people around this table. On this night there were only five of us – Todd and Rebecca, Russell (Todd’s best buddy), Clare (who was a new friend of Rebecca’s) and myself. At 19 years old, I was the youngest. Todd was oldest at 23.
The bar was packed out but we found the band pretty lousy – it was some folk trio of Irish fiddlers – and none of us were really listening. Instead we were laughing and chatting and drinking Coke by the bucketload, having consumed a few cans of beer in the parking lot before going inside.
After a while, the conversation inevitably got around to sex. This was Todd and Rebecca’s doing – partly because they initiated every topic of conversation, and partly because the two of them were so horny for each other that when they weren’t actually making out in front of us, they would be talking and showing off about it.
As ringleader of the conversation, and following a whispered private conference with Todd, Rebecca announced we were going to play a game of Truth or Dare. I can’t recall if anyone objected but they would have been unlikely to once Rebecca had decreed it.
The first person picked on for the game on was myself. Like I said before, I was still the runt of the group and clearly the one who commanded the least respect from within, even if outsiders generally now considered me to be royalty.
Rebecca asked me if I wanted truth or a dare. In an attempt to be as cool as I sincerely believed they were at that time, I casually answered “Dare”. I would have given anything to prove myself and gain standing in the group.
My dare was (without asking) to drink the half-glass of beer belonging to some tough looking guy at a nearby table. It was easier to achieve than I thought as he was engrossed in watching the band. I casually passed by and surreptitiously swiped the beer, draining it in one gulp and just as casually and surreptitiously placing it back on the table beside him.
Returning to my seat we all waited a good minute or two before the guy brought the glass back up to his mouth and seemed puzzled that it was emptier than when he last took a sip. This was met with hoots of laughter from the gang at my table and won me back-patting and accolades. I was pretty pleased with myself.
Next up was Clare, who was sitting on the bench next to me, with our backs to the wall. It was not the first point in the evening that I sensed Clare was a bit of a kindred spirit. She seemed every bit as out of her depth and yet eager to please as I was.
I could tell immediately she wasn’t as comfortable with the game as the others around the table but that like me, she was also desperate to remain a part of the group, which had no doubt improved her popularity as much as it had mine. She opted for “truth” instead of dare and Rebecca seemed delighted by this.
Rebecca had a pretty sadistic streak in her. Everyone wanted to be her friend but I wondered if anyone ever really got close to her. She took great delight in thinking up a really tricky question for Clare to answer truthfully. I think she would have done so whoever’s turn it was to answer, but seeing as she didn’t know Clare all that well yet, she was probably deliberately harsh.
“Ok my question is this…”, she said, grinning in advance at what she perceived to be her own cunning in thinking it up. “You went on the school camping trip last semester and shared a tent with Annabel Knight, right?” (Annabel Knight had a reputation for being a bit of a slut).
“Yes”, said Clare, following carefully, clearly eager to answer whatever question might be coming.
“And Annabel told us that her and Philip Crowe fucked in their sleeping bag while you were in the tent, right?”.
“Yes”. Clare was happy to confirm the story. She seemed relieved this was all she was being required to answer, but Rebecca went on.
“So my question is this. Did you get turned on by listening to them fucking?”
This was a clever question because Clare was definitely taken aback and went a little red. “No”, she said, “I just fell asleep and didn’t think about it.”.
She said it in a believable enough way but I suppose it did seem a little unlikely.
Todd and Russell expressed disbelief. I stayed typically silent.
“Liar!”, Rebecca snapped. She still had a smirk on her face, but I sensed she was a bit pissed with Clare for not playing ball.
Clare seemed immediately anxious that she had disappointed.
Next up was Russell who took a dare to throw an ice-cube at a woman sitting on her own by the fire exit. This was met with squeals of delight from our table and resulted in the woman switching seats.
Rebecca took “truth” for her turn and was asked by Todd what the biggest number of orgasms was that she had ever had in one session. She replied “seventeen”, which struck me as a lie but of course nobody voiced any doubt and instead we all sycophantically cooed with awe.
Todd also took “truth” for his turn and was asked by Rebecca whether he had ever masturbated over her. He answered “yes, every day”. This response delighted Rebecca and the game was paused for a moment while the two of them slobbered over each other’s faces.
It was a pretty sickly display – Todd and Rebecca’s questions had clearly been designed to bolster one another’s ego’s and form part of the evening-long foreplay that would later result in them making out in the back of his car.
Next it was my turn again and this time I asked for “truth”, eager to impress my friends with candid honesty as much as I had done previously with my courage and audacity.
“How many girls have you fucked?”, Russell asked, before anyone else could formulate a question.
“Er.. None”, I answered sheepishly.
My honesty was met with approval from the men at the table. Todd raised his Coke and made a pledge to change that situation for me. I smiled embarrassedly but felt good that I hadn’t tried to make something up. It would only have led to further questions and eventually I was likely to have been caught out.
All eyes turned to Clare again who, clearly aware she was considered the weak link in the game at that point, was desperate to make amends. She boldly requested a “dare”. I hoped they were going to go easy on her and yet I could see that Rebecca was still of the view that Clare was a bit of a geek.
“OK…”, Rebecca said with an evil glint in her eye.
We all had to wait in suspense for a moment as one of the bartenders cleared away the empty glasses from our table. Clare looked nervous but still determined to rise to whatever challenge befell her.
“Your dare is to take your underwear off and put it on the table” Rebecca said.
Clare tried to look unperturbed by the proposed challenge. She glanced down at her lap. From my place on the bench beside her I also looked down. She was wearing a short, loose-fitting black skirt that stopped half way down her thighs. Although I perceived she was uncomfortable, I didn’t expect for one moment that she would refuse the dare. And sure enough she didn’t.
Starting with the top half, Clare discreetly and with some dexterity, withdrew one of her arms inside the sleeve of her shirt. From here, and with all of us watching in excited silence, she went about unfastening something at her back and pulling it down over her shoulders. She carried out the action swiftly and clinically, the whole time ensuring that what she was doing was fully concealed by her shirt.
She looked inconspiciously around the room at the same time to ensure that nobody outside the group was watching. With impressive speed she eventually returned her arm through the sleeve of the shirt and dropped a peach-colored bra, scrunched up into a ball, on to the table in front of us.
Todd and Russell went crazy about this, applauding and approving her actions. In fact, their brief outburst caused two or three nearby tables to glance over at us.
Rebecca seemed less impressed. I guessed this was partly because of Todd’s approval but also because she had secretly expected (and even hoped) that Clare would refuse to carry out the dare.
By now the atmosphere around the table was tense and excitable and even though I sympathized with Clare’s predicament, I couldn’t help but be swept up in the erotic suggestiveness of it too.
My eyes stayed fixed for a while on the lacy bra that lay on the table. It was an arousing thought that Clare’s (quite impressive) chest had been set free beneath her shirt just a few inches away from where I was sitting. She was a hot girl.
Next we watched her reach beneath the table and wriggle free of her pants. The only people who might have got a glimpse of what was going on down there were Todd and myself as we were seated next to her – one on each side – on the bench. But unfortunately she was every bit as skilled at masking this action and her skirt fully covered what was going on underneath.
Once she had removed the underwear from her waist, she naturally had to get it down over her feet so she appeared to draw her knees up under the table for a moment and lower her arms in order to free herself from it. Once again just a few short moments later, her hand appeared above the table and she triumphantly dropped a tiny little teen thong on top of the bra.
“Dare completed”, she announced victoriously.
Once again the lads went crazy with approval at this but Rebecca still had the same reservation preventing her from appearing impressed.
When Clare went to retrieve her underwear from the table, Rebecca got there first and snatched it up.
“You’re not allowed it back until the end of the game”, she said bitterly.
Clare seemed confused now. She had followed Rebecca’s orders and won favor with the group but now seemed to be disapproved of even more by Rebecca herself.
Rebecca was hellbent on making her feel even more uncomfortable, when she suddenly made the following announcement: “Oh my God, her panties are all wet”.
Clare looked mortified but didn’t say anything.
“They’re soaking”, Rebecca went on, “have you been getting all horny down there?”.
I don’t know if Clare’s thong really was wet but this new method of teasing her was rapidly winning Rebecca back into the boys’ favor. They jeered and laughed at Clare and tried to cop a feel of the pants from Rebecca, although she kept them tightly concealed in her hand and would not allow them to.
Rebecca carried on with her taunting: “they’re all juicy and slimy”, she went on, “she must be a right mess down there”. I looked at Clare who was trying to keep a stiff upper lip but seemed really hurt. I felt I had to say something.
“Come on Rebecca”, I protested, “that’s not fair. Give them back to her”.
Rebecca stopped her jeering and looked at me with astonishment.
“Ooh sticking up for her now are we?”, she said turning on me, “are you hoping that if she’s turned on enough, she might take your virginity later?”.
Todd and Russell laughed even more at this and it spurred Rebecca on.
“Maybe it was sitting next to you that made her all wet”.
Goodness knows why either of us wanted to be friends with this unpleasant girl, but you know what teenagers are like. It takes time and maturity to realize there are more important qualities in life than popularity and hanging-out-with-the-right-people.
At the time, I am embarrassed to say, my main concern was simply that I might be rejected from the group. Clare too seemed more troubled by this thought than whether or not she could retain her dignity.
“OK, your turn for a dare again”, Rebecca said viciously, looking at me. “You like her so much, put your hand up her skirt”.
The boys loved this.
“You heard! Shove your hand up her skirt. Touch her. Find out how wet she really is!” Rebecca was loving the power she was commanding.
“Trying to get out of the dare are you?”
“No, I just…”
“Then DO it”.
I won’t pretend I didn’t feel awkward and embarrassed but I saw the opportunity to redeem myself by carrying out this challenge and I could see that Clare felt the same way. Her eyes met mine and they seemed to be urging me to go for it rather than risk having us both fall out with Todd and Rebecca.
So I reached my right arm under the table. Clare lifted her skirt up and replaced it over my hand. Todd let out a whoop of anticipation at this and you could tell from the look in his eyes that he was rather disappointed he couldn’t see any of the details of what was about to happen.
My fingers were shaking a little as Clare lowered her skirt over them. The first thing they found was the warm, smooth flesh of her thigh. I felt the skin beneath my fingertips instantly harden with tiny goose-bumps. I have no idea what the expression on my face was showing at this point but I know my heart was thumping.
Clare’s face was trying to keep calm but she looked every bit as anxious as I felt. Tracing my fingers along the soft flesh of her thigh, I moved my hand further between her legs until they reached their target.
I felt a strip of what seemed to be very neatly-trimmed pubic hair and a moment later touched the outer lips of her pussy. They were dry and felt cooler than the flesh on her leg.
I was not intending to have any more than a quick feel before removing my hand – having completed the dare – but as I pressed my forefinger against the fleshly lips it suddenly and unexpectedly slid inbetween them. And before Clare or I could do anything about it, my finger was met with the hot, dampest little cunt imaginable.
I don’t know how I can be so sure when Clare’s upper body and face remained so inanimate, but I felt certain she experienced a sharp sensation of pleasure when my finger slipped inside.
I had been unsurprised at the apparently dry lips that originally met my touch – I mean, being placed in the embarrassing situation of being “abused” in public as part of a dare was hardly guaranteed to be turn-on of the year – but nothing could have prepared me for the shock of discovering that just beneath the surface, her pussy was every bit as slippery and juicy as Rebecca had advertised.
By the time my finger slid back out again, the whole area of her pussy was drenched. It was the wettest little crotch I have ever touched – although I had little to compare it with at the time.
I hesitated as I returned my hand above the table, as to whether I should wipe my fingers first. I didn’t want to provide further fuel for Clare to be tormented, but then I also didn’t want Rebecca to think that Clare and I had simply “faked” it.
As it happened, I had no time to think before Rebecca was making demands again:
“Show us your fingers”, she said.
I held them in front of me and we all saw, quite unmistakably, they were lubricated with a clear oily liquid that was glistening in the dim light.
Rebbeca was delighted at this vindication. “You see”, she squealed, “she is soaking down there!”
Todd and Russell cheered their approval of this new evidence of Rebecca’s allegation and both congratulated Clare and I on our impressive carrying out of the dare.
“Now put the finger in your mouth”, Rebecca ordered and I popped the wet forefinger between my lips. My taste buds were met with the distinctive salty taste of pussy.
There were even more cheers from the boys.
“Right, its somebody else’s turn then”, said Clare in an attempt to move the game on.
“No it isn’t”, Rebecca interrupted, “you guys haven’t finished proving yourselves yet”. I don’t know if she was getting off on the power of giving out orders or if, like the boys, she was simply getting off on the forbidden nature of the activity, but either way she wasn’t ready for our ridicule to finish.
“Next”, she said, “Clare you have to flash Henry your pussy”. I was starting to feel rather fondly towards Rebecca again. If I was going to continually benefit in this way from her orders to Clare, maybe the situation wasn’t so fucked up after all.
Clare also seemed more relaxed this time. Perhaps because the ice had now been broken, or maybe because this dare was comparatively tamer than the one we had just performed.
Clare sat back as far as she could against the wall and turned her legs fully towards me. We both scanned the immediate area to be sure no outsiders were watching and then I looked down at her lap, which was still concealed by a long skirt.
With her legs parted noticeably farther than the dare would have required, she lifted her skirt and held it aloft for what can have been no more than a three-second flash. It was enough time to afford me a delicious view of her beautiful naked thighs and little pink cunt, with its lips ever so slightly separated and glistening with sticky dew.
Once the skirt had come back down again I could see from Todd’s expression that he was delighted by our collective nerve but also a little frustrated that he hadn’t got a better look himself.
There was a vast round of applause for us from all three of the others at the table and even Rebecca seemed to have calmed down slightly and was acting more impressed with the guts we had shown. It was a good feeling. We were popular again.
“OK”, she said, retaining all the authority in her voice, but attempting a more conciliatory approach, “one final dare and then Clare can take her underwear back and the two of you will have won the game”.
Neither of us had been aware it was a game with a possible winner, and I still couldn’t see how all the other players but Clare and I had suddenly been made exempt from having to take part, but I was just delighted we seemed to have Rebecca’s approval again. Moreover, that the whole table seemed to think we were pretty cool for a minute.
“The last dare…”, she said, pausing either for effect or to decide quite how extreme she should make it, “is…”
The whole table waited with baited breath.
Todd whispered something to Rebecca and she squealed with delight. “Clare”, she finally said, “you have to jerk Henry off.’
Clare and I were clearly quite shocked by the extremity of the dare but we tried to appear as casual about it as we could. Rebecca was bombarded with requests for clarification from the others: “For how long must she do it?”, “Does it have to be more than a couple of strokes?”, “Do they have to do it in the toilets?”
Rebecca cut through all the questions and stated the rules clearly and matter of fact-ly. “She has to do it here and she has to do it right now. Under the table. And she has to do it for three minutes exactly”. At this pronouncement Rebecca removed the watch from her wrist and placed it on the table. “I will be the time-keeper”.
Nobody asked Clare and I if we were up for the dare, but then it wasn’t presented to us as though we had any choice. It was quite a pleasant forfeit anyhow for me, although I would have far rathered it were to take place in private.
Clare characteristically showed very little objection but hardly seemed enthused by the idea either. She began by rolling up the sleeve of the right arm on her shirt, quite formally, like she was preparing to milk a cow.
“Come on”, she said to me, almost impatiently, “undo your pants then”.
I felt a bit exposed. Even though this was going to be happening under the table, anyone to the right of me could very easily look over and see what was going on. It was not that dark in the bar.
I voiced this concern in as casual and calm a way as I could. It was agreed that Todd would move seats and Rebecca would come over to sit on my right, so that I was in the center and concealed by one of the girls on either side.
Rebecca permitted this concession so she could be sure we were not cheating (or at least so she said). Everyone seemed nervous and excited – myself and Clare included.
So here we were, Rebecca and Clare on the bench with me sandwiched in between, all of us with our backs against the wall. Opposite us, and with their eyes virtually popping out of their heads were Todd and Russell, looking like a couple of kids on Christmas morning.
Nervously I began to fiddle with my belt. Clare was impatient with the time I was taking and reached down to assist me. I unbuttoned my slacks and pulled the zipper down, all the while trying to calmly survey the crowded bar in case anybody suspected anything. Nobody appeared to have a clue.
Lowering the waistband of my pants and boxer shorts down, I felt my bare backside sit back against the wood of the bench. I wasn’t in an aroused state anymore – feeling nervous suddenly, more than anything else. What would happen if I didn’t ‘rise’ to the occasion? I would surely never live it down.
Rebecca glanced below the table and saw that I was ready. She made no comment about my flaccid state and neither did Clare, who could also now see from where she was sitting, on my left..
Rebecca held her hand aloft and looked at the watch. “Right I am starting the three minutes… NOW”.
An instant later I felt Clare’s warm hand uncurl my limp penis and hold it in her hand. To my relief (as well as my unbridled fear) I felt it soon begin to stiffen in her hand. She started to work her fingers up and down on the shaft, gently tugging the skin up and down.
I had so many mixed feelings at this point – the fact that I was in this very public place, that I was involved in a filthy dare, that four people’s eyes were fixed on my upper body in the knowledge of what was going on beneath the table – all these things were at once both terrifying and arousing.
I felt myself becoming harder by the second and as Clare’s jerking motion became freer and more easy, I started to wonder if she’d done this before.
“One minute…” Rebecca suddenly announced. It made me jump as nobody around the table had said anything for the previous sixty seconds.
Clare continued the delicious movement of her hand up and down, and with every new stroke I felt the inhibition and fear drain away only to be replaced by an overwhelming sensation of pleasure.
At that moment the bartender walked past our table with painfully close proximity, collecting glasses from some other customers nearby.
“Don’t stop”, Rebecca whispered. And Clare obeyed, although she did slow her jerking so it was not quite so visible in her shoulder movement until he had gone past.
“Two minutes”, Rebecca announced. I noticed she was studying the watch-face with far less careful attention now than she had been. Instead she was sitting back and trying to get as good a view as she could of the activity beneath the table.
There was probably not much she could see from where she was sat so, feeling more daring now as the lust began to consume me, and always one to give Rebecca what she wanted, I shuffled back on the bench. In doing so, my waist and thighs appeared more clearly from under the table and Rebecca was given a clear unhindered view of my stiff cock being massaged back and forth by Clare’s fist.
Todd and Russell stole every opportunity to not-very-discreetly peer under the table and watch Clare tugging away on my now-huge erection.
“Oh my God”, said Russell, having managed to even shock himself by the brazen audacity of it.
Knowing that the boys were stealing glances my way, I decided to give them a more exciting show and reaching my own left arm under Clare’s wanking-hand. I pulled her skirt up to expose her crotch and began playing with her juicy little pussy again. To my delight it was even messier and more slippery than before.
Rebecca seemed to be getting more aroused by what she saw now, as she started to whisper questions at Clare, like: ‘is it as thick as it looks?’ ‘Does it feel good?’ She even spat on the tip and let Clare rub her saliva over the shaft.
I was feeling so turned on by now that it occured to me I wasn’t going to make the full three minutes without cumming. This was something I’d forgotten about, what with my fear as to whether I would achieve an erection or not.
I wasn’t quite sure what to do… Surely the three minutes was almost up. Could I hold off? I tried to slow Clare’s hand a little with my own but she paid no attention and instead started to jack me off even harder.
Should I announce what was going to happen?
I had controlled my external appearance enough so that there was nothing to outwardly indicate to the others what I knew was about to happen.
“Ten seconds to go”, Rebecca said, her eyes immediately returning to my cock as she began an audible countdown.
But it was too late.
Without anyone but myself having advance notice, a long stream of spunk suddenly shot out of my cock and up into the air a good foot or so above the level of the table, and came splashing down to rest on my shirt.
“Fucking hell!”, Todd exclaimed.
“He’s cumming”, Rebecca announced – as if anyone could have missed this obvious fact. Clare, I noted, did not stop jerking me, despite the fact the three minute deadline had clearly past.
Naturally this was all happening very quickly so I imagine Rebecca had little time for prior consideration when she unexpectedly leaned over so that her head was a few inches from my cock and Clare wanked a second third powerful stream of sperm directly on to Rebecca’s lips and chin, and she sucked it into her mouth to taste.
A fourth and fifth ejaculation fired further missiles of spunk up on to the table top. After a couple more blissful eruptions, I was spent and Clare brought her masturbating to a close.
Todd and Russell were now transfixed on Rebecca who had sat back up licking my semen from her lips.
I can only guess that she had intervened in this way at the last minute to try and ensure the attention was back on her, rather than Clare.
And it had definitely succeeded.
“You horny bitch”, said Todd grinning, but insanely jealous and angry with her, while Russell managed little more than a wide-eyed “wow!”
“Dare completed” declared Clare proudly, while I hurriedly pulled up my pants.
“OK, I’m impressed”, said Rebecca wiping her mouth with a napkin. She was able to willingly acknowledge this perhaps because nobody, myself included, was more impressed than with her own behavior.
Clare and I were considered cool and welcomed into Todd and Rebecca’s clique for at least another three or four weeks after this event, until eventually they grew tired of us, and replaced us with a few other unsuspecting nobodies.
We were both upset at the time but hey, didn’t somebody once say it is better to be a ‘celebrity’ for five minutes than never to be one at all. And that night we were heroes amongst the coolest guys in school.