“Take me home and you won’t need those”
I turned round, was that aimed at me?
Oh shit, one of my sixth-formers, I forgot she worked here.
“Oh, Hi Chloe, what did you say?”
“Those condoms you just put in your basket, you won’t need those with me.”
“What do you mean?”
“I’m on the pill, no need to bag up with me.”
How do I reply to that?
“Mmm very sensible, I’m sure your boyfriend appreciates that.”
“I don’t have a boyfriend, that’s not why I’m on the pill, they’re for painful periods.”
“Mmm right, do you know how we’ve spoken in the past about how some details are best kept private.”
“Oh yeah, sorry, this is one of those times, right?”
Chloe gave a nervous giggle, and I was struck by how pretty she is. I’ve taught Chloe on and off since year 7, soon she would be leaving at the end of year 13. I try to resist getting too close to students, sometimes the temptation is very strong, but so far I’ve resisted it. Chloe though was always quiet, and I’d not previously thought of her as being particularly pretty, but today, out of the context of school I changed my mind, she is very pretty indeed.
I had to get out of this potentially messy situation, “Well, nice meeting you Chloe, but I have to be going.”
“See you later Mr Hughes,” Chloe replied, in a very low sultry voice.
I paid for my purchases and quickly left the store.
After that trauma I needed a drink, and up the road is my very favourite pub, it’s only small but they have live music most of the day and the best beer in town. I ordered a pint of Wobbly Bob and a bowl of sweet potato fries with chilli dip then took my usual table by the window.
On Saturdays they have a pianist in, she plays a mixture stretching from easy listening standards to improvised jazz, whatever takes her fancy. It’s an almost perfect way to spend a Saturday afternoon.
I was part way through my second pint when the door opened and Chloe walked in, turning her head from side to side, checking out the room. She saw me and beamed, and I’m ashamed to say so did I.
“Hey Mr Hughes, fancy seeing you here.”
“Hey Chloe, what I surprise, I’m in the same pub I visit every Saturday, and I suspect I’ve mentioned this more than once.”
“Busted, although this is the third place I’ve looked.”
“What do you want Chloe?”
“A Bacardi & Coke please.”
“That’s not what I meant, why are you following me around?”
“Get me a drink and I’ll explain.”
“You are 18 right?”
“Yep, for a couple of months now.”
I returned to the bar for Chloe’s Bacardi, I ordered myself a double of Four Roses bourbon, I also ordered another bowl of sweet potato fries, they really are delicious.
Back at the table I handed Chloe her drink, her fingers brushed mine as she took the glass and I felt a spark, oh god, don’t let this happen.
“So, what’s this all about?”
“I think you know.”
“Well, I’ve got an idea, but why now?”
“Because in a few weeks the exams start, then a few weeks after that we all leave and I might never see you again, and there’s something I need to do or I’ll regret it for ever. Or more accurately, something I need you to do.”
“And what would that be?”
“It’s not really something I want to discuss here, it’s a little personal.”
“OK, where can you discuss it?”
The second bowl of fries arrived at this point, Chloe took one and dipped it in the chilli sauce, “mmm delicious, but wow that dip is hot. Anyway, as I said, private and delicate, so somewhere a little more private.”
Maybe this isn’t what I expected, so I took a deep breath and plunged forwards.
“All right then, I’m free tonight, so I’ll take you out for dinner, an early celebration of exam success.”
“Cool, that’ll be really nice. So ... if you’re free tonight, why’d you by those condoms?”
“Well, my girlfriend is away at the moment, but she’s back on Tuesday, and I won’t be shopping between now and then.”
“Ahh, planning a hot night on Tuesday then, nice, Oh shit I have to get back to work, I’m already late. Here’s my number, call me to tell me where and when to meet.”
As Chloe left I hung my head, what have I done? At least Chloe is 18, so I’m not in danger of jail, but I could lose my job, and be disqualified from teaching, so I had to tread very carefully tonight.
Chloe obviously wanted somewhere quiet to talk, so I booked a table at a wonderful family owned Italian restaurant, they serve you and disappear, just what was needed tonight. I phoned Chloe with the where & when, didn’t want a text from my phone sitting on hers, and I didn’t want her having my number either, so I called from a payphone, then I went home to shower & change.
Chloe was right on time, meeting me at the restaurant door, we were led to a table near the back, overlooked by none of the other tables.
I took a long look at Chloe, which is wrong, but I’m a man, so what can you do. She was wearing a white Ted Baker top, open a couple of buttons to show some cleavage, a pleasing sight.
A waiter arrived as we sat, brandishing a couple of menus and a basket of garlic bread.
“Oh, this is nice, I had no idea this restaurant was even here.”
“I’ve been coming here since I was at university, it’s never busy, but they must make enough to keep going, all the staff are family. The pizzas are divine, very thin bases, cooked in a wood stove.”
We both ordered pizza, I had the chicken and mushroom, Chloe ordered goats cheese and spinach, I ordered a bottle of Barolo.
The pizzas were, as always, delicious, the wine was superb, but maybe a little overpowering as an accompaniment to a goats cheese pizza, then again it’s not the ideal match for chicken either, but I like it.
Chloe ordered an orange gelato for desert, I ordered a grappa and an espresso.
“So Chloe, what exactly is this favour you need from me?”
Chloe licked her spoon clean and placed it in her now empty bowl, “Well, this is kind of embarrassing”, although the light was poor in our corner, I could tell she blushing.
“I can keep a secret Chloe, I keep many secrets, I know things about your classmates that would make your eyes water, and they will remain secrets.”
“Okayyy, let’s plunge in head first ... I want you to take my virginity Mr Hughes.”
“Right let’s stop right there. Firstly, ending that sentence Mr Hughes is all kinds of wrong, so for the rest of this conversation please call me Danny.”
“OK Mr Hughes, sorry, Danny.”
“Secondly, are you out of your mind? That’s not something I can do, I could lose my job, and besides, losing your virginity, that’s a job for someone you love.”
Chloe had tears in her eyes.
“That’s the general idea, I love you. I have since, well since you were my form teacher in year 8. It’s the Prom coming up, a guy’s asked me, I don’t really like him, but I’m not going on my own. I’m assuming he’ll try to get me into bed at some point during the night, I do not want that to be my first time.” This all came out in a rush, almost as if she had to say it in one breath or not at all.
“Oh my, I see. I’m afraid I’ve still got to refuse.”
“Don’t you think I’m pretty?”
“Well yes, you’re very pretty, but as a teacher I’m bound by certain rules, even though you’re 18 I can still lose my job if word gets out.”
“Look I can keep a secret, for instance, I bet one of the secrets you know is about Tracey White, a cucumber and the Food Studies kitchen. I’ve known about that for 5 years and never told anyone.”
“It’s not you I’m worried about, my neighbours have eyes, and you don’t look anything like Lorraine.”
“How different are we?”
“Well you’re about 6” taller and, err, quite a bit bigger up top, and she’s blonde, you’re a redhead. I think they’d guess I was bringing a different girl home.”
“Heels, wig & a booster bra, problem solved,”
“What’s a booster bra?”
“It’s a girls version of putting a pair of socks in your underpants, it lifts and squeezes your boobs, makes them look bigger.”
“Cheating you mean? No Lorraine wouldn’t wear one of those, way too proud of her petite frame.”
My resistance was wearing thin, and, it was gone.
“OK, but if word gets out you’re in deep shit lady...”
“My lips are sealed Mr Hughes.”
“Oi, tonight I’m Danny remember.”
I paid the bill, Chloe tried to chip in half, but I’m a gentleman, a gentleman who’s about to break all kind of child protection rules and cheat on his long term girlfriend, but still a gentleman.
“Hey Danny, let’s get a couple of drinks first, will it be safe for us to go to that bar again.”
“Oh yeah, it’ll be fine, everybody is cool there.”
We had a couple of drinks, Chloe back on the Bacardi & Coke, I had more of the wonderful Four Roses, then we wandered over to the Best Western across the road from the pub, they had a deluxe double available, I’ve stayed here before with Lorraine, the rooms are tired but comfortable, Chloe was impressed with the view of the castle.
“So, what now?” She asked.
“Now we do whatever you want to do, and nothing else. If you want to just go to sleep then curl up in the bed and I’ll sleep on the sofa.”
“I want you to undress me.”
Ok, I can manage that.
I stepped in close, Chloe was trembling, but her eyes were locked on mine, and they showed no fear, just a hint of trepidation, like something she’d long dreamed of was about to come true. For my part my mind was still whirring, at the back, being beaten into submission by my growing horniness, was a thought that this may just be too good to be true, and that on Monday I’ll lose my job, and on Tuesday my girlfriend, but right about now that thought was all but dead.
I gently took hold of Chloe’s blouse and unfastened the first button, then the second and third, the blouse fell open, revealing an ivory bra with lace flowers.
“Do you like?”
“Yes, I like it.”
“I bought it for you this afternoon. It cost me a day’s wages, so please be careful when you take it off...”
“I’m going to be very careful, with everything...”
“I know you will, I trust you completely Danny.”
I unclipped the very pretty bra and carefully pulled it away from Chloe’s body, her breasts were bigger than I imaged, I sneaked a look at the tag as I laid the bra on the dressing table stool, 32E. I’m going to be really spoilt with Chloe’s boobs, Lorraine is only a 32B.
I leant in close and kissed her left nipple, taking it into my mouth, nipping it gently, flicking it with my tongue. Chloe let out a low moan and grasped my head in her hands. I swapped to her right nipple, Chloe gripped my head tight, holding it in place. I felt a shudder run down her spine and the pressure on my head increased as she let out a cry...
“Oh my God, oh my, ahhh Danny don’t stop that, it’s incredible, ohhh I’m cuming, I’m cuming shit yeah, oh ... my ... god...”
Chloe let go of my head and fell back onto the bed, panting.
“Holy shit man, that was incredible, who knew I could orgasm from having my boobs fiddled with?”
“Talking of boobs, where do you hide that magnificent pair during the week?”
“At first, when they started to grow, I was ashamed of them, all the other girls had tiny boobs, and I had this huge pair, I felt a bit of a freak, so mum took me to a really old fashioned bra shop in Morecambe, I don’t think any of the staff were under 60, apparently they used to supply underwear to the Queen’s mother or something, she bought me a minimiser bra, which takes some getting used to, but it kept my boobs in check at school. I’ve worn them ever since, mostly because otherwise everyone would wonder where my rack came from overnight if I stopped wearing them.
“Luckily I don’t hang around with many of the girls from school, so I can let them breathe at weekends.”
“They’re beautiful Chloe, and they’re the right size for your body.”
“Thanks, that means a lot from you. Anyway, only a few more weeks, then I can throw the strappings away, make a fresh start at Uni with these whoppers from day one.”
“Anyway, where was I? Oh yes, I think you’ve still got too many clothes on.”
I helped Chloe to her feet and knelt before her, first I removed her shoes, I couldn’t help noticing the name inside, Jimmy Choo, I raised my eyebrows.
“They’re my mum’s OK, and she doesn’t know I’ve borrowed them, so be careful with them, she’ll go mental if I mark them.
“I’ll treat them with the utmost care honey, look how gently I place them on the floor under the dressing table”
“Thank you, you really are a gentleman.”
Reaching out I unclasped the buckle on her belt, then unfastened the buttons on her jeans, I pulled them down and Chloe stepped out of them, the jeans didn’t look precious, so I tossed them to one side.
“Oi, treat all my clothes with respect or I’m going home.”
“You’re leaving in just your knickers if you do.”
She gave me a gentle slap, so I pulled her knickers off and pushed her back onto the bad, laughing as I fell on top of her, we kissed, I could tell she wasn’t an experienced kisser, but she put her heart and soul into the job, 11/10 for effort.
I broke the kiss and came up for air, then I moved down her body, kissing every square inch of skin as I travelled south, I spent some time on her boobs, as they were an obvious point of extreme excitability for her. Chloe gripped my head again as she came, harder this time, her back lifting off the bed as the orgasm coursed through her body.
I waited a minute or so for her breathing to settle, then I continued my journey, when I reached her navel I stopped, she had a piercing, I’d not noticed it before, probably because I was transfixed by her magnificent breasts, oh what a typical male I am. Anyway, piercing, she has a silver ring with a little red stone in it, it’s very pretty and I admire it for a moment.
“Oi, stop admiring the view and get back to work.”
Chastened I got back to work.
Chloe had a tiny patch of red pubic hair, shaved to a neat triangle, I moved my fingers down and gentle parted her pussy lips, beyond was a virgin pussy, to the best of my knowledge I had not previously taken anyone’s virginity, so tonight promised to be a first for us both.
I flicked her clit-hood with my tongue, Chloe arched her back and gave out a long, low moan, at the same time her clit popped clear of its hood and I gave it some more attention, I also slid my ring finger inside her pussy entrance, at the second knuckle I felt some resistance, she is indeed a virgin. I pressed my finger against the base of Chloe’s clit whilst I continue to work on its head, Chloe came almost immediately, she also squirted a fair amount of pussy juice in my face.
In all my years I can’t remember a girl who could orgasm as easily as Chloe. This was her third orgasm in about 10 minutes and I’d not even started yet.
Before she’d calmed down properly I thought I’d try something, I slipped my finger out, it was well lubed from her sopping pussy, and I carefully pressed it against her bum-hole.
“Oooo, you naughty boy.”
“I won’t if you don’t want me too.”
“It’s ok, go ahead, but be gentle, that hole is just as much a virgin as the front one.”
Very carefully I pressed my finger into Chloe’s anus, a little more pressure and it popped inside, Chloe’s bum pulsed at the intrusion and she gave a low moan. I pushed the finger a little deeper, until it was as deep in her bum as it had been in her pussy, then I started to slowly finger fuck her bottom.
Chloe squirmed with pleasure and I had to concentrate to stop my finger coming all the way out.
As I felt her nearing orgasm I pushed my thumb into her pussy and worked it against my finger, just her pussy wall between them, and started back on her clit with my mouth.
Looking up, along her body I saw Chloe was working on her nipples with both hands, and she had the corner of the duvet in her mouth to stop herself from screaming the hotel down as she came to a massive climax, her whole body lifting off the bed, her pubic bone pressed hard against my face and hand. She dropped down to the bed and bucked several more times before she stopped, panting, her whole body gleaming with sweat.
I moved to the desk chair and sat, watching my young lover, mesmerised by the rise and fall of her magnificent breasts as she filled her body with oxygen.
“Honey, you OK?”
“I’m absolutely fine, in fact I’ve never felt better.”
“I’ll tell you what, while you get your breath back I’m going to pop over the road to get a bottle of champagne and a couple of glasses. I’m sure Mark has better bubbly than this place. I won’t be a minute.”
“Hang on a sec, come here.”
I moved over to the bed and Chloe pulled my face close to hers, then she licked me from chin to forehead, finally planting a hard kiss on my lips.
“There, that’s better, couldn’t have you popping into your local covered in pussy juice. Damn I taste good. Hurry back lover...”
As I opened the door she called me again.
“Oh, do you think it would be cheeky to ask him to send across a serving of those sweet potato fries?”
“I’ll ask, maybe Jenny the barmaid could deliver them and join us.”
The pillow she threw hit the door as I closed it.
I was back in a couple of minutes as promised, Mark just sold me a bottle of Laurent-Perrier Rosé at cost, I either looked horny as hell, or just plain desperate. He also threw in a couple of Cristal branded glasses for the full hip-hop experience, Jenny is going to pop across in 10 minutes with the chilled champagne and fries, she’s definitely not stopping though, although her blue hair and tattoos would provide a nice contrast to Chloe’s pale body and naturally red hair.
As promised Jenny arrived with the rosé champagne and fries, she looked Chloe up and down, she was still sprawled naked across the bed, and winked.
“If you need anything else Danny just give us a call next time, you don’t want to be leaving this hotty for too long. I’m working until 4am, pretty sure you’ll not be asleep before then.”
Jenny gave Chloe one last look then left, closing the door gently behind her.
I popped the champagne and poured a couple of glasses.
“Cheers Chloe, you hotty...”
Our glasses clinked and we took a mouthful each, Mark was right, this is special stuff.
“She fancies you Danny.”
“Nope, she fancies you.”
“Yep, she’s 100% gay. I know because a couple of teachers who’ve tried it in on and failed. Remember Miss Holmes?”
“The PE teacher who left last year?”
“That’s the one, she’s the only teacher who’s succeeded, she dated Jenny for a few months.”
“Miss Holmes is a lesbian?”
“She sure is.”
“Wow, I knew the lesbian PE teacher is a stereotype, I didn’t think it was true. Wow I need to get my gaydar fixed, I might be missing out on some lady fun.”
“Anyway, where were we?”
“Well I’ve cum, 4 times is it? And you’ve still got your all your clothes on, so I think it’s my shift, now not wanting to break the mood, but everything I’m about to do is purely from books and films, so forgive me any amateur mistakes.”
“It’s OK honey, really, just relax and do only what you’re comfortable with.”
“First let’s remove some, or perhaps all, of this clothing.”
Chloe unfastened the buttons on my shirt and I shrugged it off my shoulders, she tossed it across the room, giggling as she did it.
“Oi, that’s a Tommy Hilfiger, I was careful with your clothes.”
“It’ll be fine, it’s neither silk nor Jimmy Choo, now be quiet, I’ll lose my concentration and decide to just go to bed.”
Chloe ran her hands over my torso, I’m neither ripped nor fat, just your average bloke who tries to keep himself in shape.
“Nice, I like a man with some chest hair, those models you see who’re all waxed look like they spend longer getting ready than a girl.”
She moved her hands lower and cupped my cock through my jeans, she nodded approval then moved down to my shoes, removing them in turn and tossing them after my shirt, my socks followed in their wake.
Chloe then knelt down so her head was level with my belt, she unbuckled it and then unfastened the buttons on my jeans, pulling apart the waistband my jeans fell to the floor and cock sprang loose, it just missed her chin as it shot up to horizontal.
“Mmmm, now this is nice,” she caressed it with both hands, her lips touched the head, which was very tender after being excited for the last hour or so, there was a little dribble of pre-cum on the tip and Chloe picked it off with her tongue, savouring the taste. “It’s big, isn’t it.”
“Well I wouldn’t know, I don’t go round comparing it in the gym.”
“What does Lorraine think, does she say it’s big.”
“I’d rather not talk about Lorraine at the moment, if I’m honest.”
“Sorry, my bad. Anyway, it’s me that’s important right now isn’t it, and I’m more than happy.”
“That’s good enough for me.”
I could tell she was babbling because she was nervous. I stroked her hair, she relaxed and opening her mouth took a good 50% of my cock inside, I gasped with surprise, I did not expect this to happen so soon. Chloe closed her lips around my shaft and bobbed her head back and forth, her tongue tickling my cock head all the while.
I was stunned, had she been taking lessons?
All of a sudden she pulled her head away and took a few deep breaths.
“Was that OK?”
“Look at my face, does it seem unhappy to you?”
“No, it doesn’t”
“Then you’re doing fine.”
“Oh hang on, I forgot something.”
She got up and walked round to the dressing table, she picked up her glass and topped it up from the almost empty bottle in the ice bucket.
Kneeling back down before me she took a sip of her champagne then immediately took my cock in her mouth, oh my, now that is a new sensation, the bubbles on her tongue really go to work on my cock head, I had to take hold of Chloe’s head to keep myself steady.
She picked up speed and within a couple of minutes she had almost all my shaft in her mouth, I could feel my head sliding into her throat, the pressure was exquisite and I doubted I could last much longer.
“Honey, I’m going to cum soon.”
Chloe just carried on, in fact she worked even faster, taking hold of my balls she started to squeeze my sack gently, rubbing my balls together. This was starting to be pure, delightful torture, and there’s no way I could last a second longer.
I held Chloe’s head tight to stop her moving anymore and with a grunt I let go, jet after jet of hot cum sent down her throat, I pulled my pelvis back slowly, withdrawing my cock from her throat, I hadn’t quit yet, a few more dribbles of spunk landed on her tongue and finally her chin.
I could barely stand, so I turned and fell backwards onto the bed, panting. Chloe lay down next to me, her head on my chest, and we stayed like that for a few minutes.
“Tell me that’s not the first time you’ve given someone a blowjob.”
“That IS the first time I’ve given someone a blowjob, I told you Danny, you’re my first.”
“But it was mindblowing.”
“I’m glad, because I’ve been practicing for ages on cucumbers, I read this book I downloaded called 100 ways to blow your man’s mind, I’ve got lots of tips from there. Let me tell you it takes a long time to learn how to suppress the gag reflex and take a cucumber to the back of your throat, I didn’t want to throw up on you.”
“Chloe, be straight with me, how long have you been preparing for tonight?”
“About a year, don’t be mad, I’ve loved you since I was about 13, then after my AS levels last year I realised I had 12 months left to get you into bed, so I’ve been making plans. Today though was pure luck seeing you in the shop, so I just grabbed my chance.”
She reach down and took hold of my cock, it immediately sprang back to life, she massaged it until it was rock hard, then she rolled off me and onto her back.
“Take me Danny, take my cherry now.”
“OK, if that’s what you want. I’ll be gentle, but the first time will hurt, and you will bleed a little. In fact I’ll get a towel from the bathroom for you to lie on, so we don’t ruin the duvet.”
I quickly grabbed a towel, Chloe lifted her bum off the bed and I slid the towel underneath, she lay back down and spread her legs for me. First I knelt before her pussy, I parted her lips and slipped a couple of fingers inside, she needed to get used to something larger than a single finger first. Chloe gasped as I parted my fingers, spreading her wider still. I slowly inserted two fingers from my other hand, moving all four fingers back and forth until she started to lube once more.
“Stop teasing me Danny and fuck me now!”
I obeyed once more, withdrawing my fingers slowly, I then pressed my engorged cock against her opening, I swear my cock has never been this big and this hard before, Chloe has got me hornier than I’ve ever been.
I applied forward pressure and my head breached the entrance to Chloe’s pussy, she let out yelp and I immediately stopped.
“It’s OK, carry on, just a shock having something so big inside. Go slowly but I’m sure I can take it all.”
I moved my hips closer to Chloe’s, slowly inserting more of my length inside her pussy canal. I stopped again when I felt resistance from her hymen.
“Right, this is the painful bit, I have to tear something inside to go any further.”
“Do it quick, like when you take a plaster off, quick pain is better than slow pain.”
I quickly pushed on and through, I felt the barrier tear, then I stopped again.
“Oh shit that hurts, please hold me for a minute.”
I reached round Chloe and held her in my arms, we kissed, tenderly, then passionately, I slowly withdrew my cock until I was nearly out of her pussy, before pushing equally slowly back in, I gradually picked up momentum until I was fucking Chloe hard, she took everything I could give and more.
I lost track of time, I’ve no idea how long we made love, but eventually my balls gave their usual warning.
“OK, I’m about to cum, you sure you’re on the pill.”
“Positive, just give it to me, I want to feel you shoot inside me.”
I gave a few more thrusts until the dam burst, I slammed into her hard and let go, blasting streams of spunk deep inside Chloe’s waiting pussy. I held still, my cock continuing to pulse long after I was fully spent.
Chloe hugged me tight, her pussy pulsing in time with me, her muscles performing miracles, massaging my dick back to hardness, she swung her body sideways and rolled us over so she was on top. She rotated her pelvis and pulsed her muscles until I was at full hardness again, then she sat up and started to fuck me, bouncing up and down on my cock like a pro, her boobs swinging in time, hypnotising me like a magician with a pocket watch, I couldn’t help myself, I took a breast in each hand, feeling their weight. They were soft and warm, and quite heavy, this was a real luxury for me, I’ve always been a breast man, but Lorraine, as lovely as she is, she isn’t blessed with big boobs. As she rode me, Chloe came at least once, her pussy clamping hard each time, and one time she squirted copious quantities of pussy juice all over my stomach.