Becoming Charlotte – Part 5: Making the most of it 2 of 2

Over the next few days we prepare for the date, each of us doing our best to work up our respective parties excitement. By Saturday Sally is wishing the hours away til our night out, chatting excitedly as the stylists work on our hair, practically skipping as we walk back to the institute and arriving at mine and Andy’s room nearly 10 minutes early looking like a million pounds, the dress hugging her figure, her high heels accentuating her legs and ass, the bra and slightly loose top showing off her ample chest and cleavage (If Josh doesn’t make a move on her tonight he’s mad. Hell, I’m tempted to myself and I wouldn’t blame Andy if he did!).

Thankfully Andy and I are just putting the finishing touches to our outfits (though I did have to lock myself in the bathroom to put my dress on as I could see he was barely keeping control after seeing me in the freshly laundered red silk set again and we didn’t have time for any naughty business). We meet Josh at the entrance, his jaw literally dropping when he sees Sally. Regaining his senses he offers his arm to her which she gladly takes and we walk outside looking like the belles of the ball hanging off the arms of our respective tuxedo clad man until we climb into the limo (the boys being perfect Gentlemen) and it whisks us away to the most exclusive restaurant in the city.

 

(Well, dear reader, you re-join us near the end of the date, I really don’t want to bore you with insignificant details, suffice to say, it is going extremely well to say the least).

 

Every time Sally leans forward to talk to me, Josh’s eyes are immediately drawn to her chest and his face flushes with desire, though the same happens every time they speak to each other which, to be honest, has been a lot. In fact, Andy and I may as well have not been there as they’ve been mostly talking between themselves and asking questions about the each other. We don’t mind though, as it’s a good sign our plan is working.

Just after we order our desserts Sally gets up, saying she needs to use the little girls room and asking me if I’d like to join her. It’s obvious that she needs to speak to me so I follow her, both of us getting some very admiring looks as we pass by the other patrons. We enter the ladies room and Sally leans back against the expensive sinks, looking at me with a hint of apprehension.

“I have a problem…” she begins, blushing. “I have an itch… down there.”

“An itch?” I look at her quizzically “Time of the month?”

“No, a different kind of itch…”

“An infection?”

She shakes her head, biting her lip.

“An itch only Josh can scratch…” she says, hintingly.

“Ohhhhhhh!” it finally clicks, I chuckle slightly. “So let him scratch it then.”

“I want to but…” she looks at the floor. “I don’t want him to think I’m some sort of a slut.” Looking back up at me “I want it to be the start of… us… as a couple… You know?”

“Do you want me to do a little probing? See if he’s going to ask you out?”

“Could you… please?” she looks at me with pleading eyes “I’m not brave enough to bring it up.”

“Leave it with me,” I tell her reassuringly “I’ve got your back.”

“Thanks Charley, I really appreciate all you’ve done for me.” She hugs me, I can feel how nervous she is.

“What are best friends for?” I say, gently rubbing her arm. “C’mon, let’s get it sorted.”

We head back to the table and I whisper to Andy that I need a minute alone with Josh.

“I’ll get us some fresh drinks…” he says getting up and turning to Sally. “Care to give me a hand, Sal?”

She nods and they head to the bar, I sit and watch as Josh stares at her retreating form, completely engrossed.

“She’s something special, isn’t she?” I ask, breaking his revelry and making him jump.

“She sure is…” he begins, his cheeks turning bright red at being caught gawping at her. “Charley… I…” he looks down at the table, sighing.

“What’s wrong?”

“I’m not sure it’s something I should talk to a woman about…” he says “I don’t want you to think negatively about me for it.”

“You do remember what I used to be, right? I understand the male side of things. You can tell me.”

He takes a deep breath, looking at  me nervously.

“OK, I’ll tell you,” he says after a pause “the thing is… I want her, not just sexually, I want her completely, to be her boyfriend. The more I get to know her, the more I see… I just don’t want her to think I see her as a piece of meat, another notch on the bedpost… I want to be with her, like you and Andy are.”

I nod, showing my understanding and chuckling a little internally at how easy this problem is to solve.

“Just tell me one thing,” I look at him sternly “if anything happens between you and her tonight, it’s definitely the beginning of a proper relationship. That there’ll be no ditching her in the morning.”

“Charley, I’d marry her tomorrow if I could.”

“Good enough for me.” I tell him with a warm, friendly smile. “Go for it.”

“Really?” he looks surprised and a little apprehensive. “You think she’ll agree?”

“Really. Don’t tell her I told you this, but she wants the same as you, and to be your girlfriend. She’s just worried you’ll think she’s easy if she sleeps with you tonight.”

“Not a bit! I know she’s not like that.”

“So do it, ask her out.”

“I will.” He responds with a grin and a wink. “Wish me luck.”

“You won’t need it.” I reply with a knowing smile.

As Andy and Sally approach the table, Josh gets up and speaks to her, gently taking her arm and leading her to a quiet spot in the restaurant, just out of view. Andy puts the tray of drinks on the table before sitting down and giving me a quick kiss.

“What’s that all about?” he asks me, nodding in the direction the others have taken.

“Wait and see.” I reply, a sly smile on my face.

A few minutes later, Sally and Josh return to the table, Josh wiping lipstick marks from his mouth and cheeks with a tissue as Sally grabs my hand and apologises to Andy as she needs me for ‘girl talk’. She literally drags me to the ladies room, turning and hugging me as soon as we’re through the door.

“He asked me out!” she says, beaming from ear to ear “Oh thank you! Thank you! Thank you!”

“Hey, no problem. “ I tell her as she squeezes the life out of me with her hug.

“He’s invited me back to his room,” she says, finally letting go and letting me breathe “should I go?”

“You’re horny aren’t you? He is now your boyfriend, isn’t he? go get yourself laid, girl.”

“You’re right, I want him, I’m having him!” she pauses, a little unsure. “He won’t think I’m a slut will he?”

“I have it on the best authority that that is the last thing he would ever think of you, he just wants to be with you the way Andy is with me.”

Sally looks at me with a wide grin and we return to the boys, Sally giving Josh a passionate kiss and rubbing his crotch as she sits. Their behaviour changes completely, gone are the two shy people who like each other but don’t dare to make a move, now they act like a true couple, taking every chance to kiss and caress each other, even feeding each other dessert.

As we part ways back at the institute, Sally gives us a hug and a little wave before hanging on to Josh’s arm as they head to his room.

“She’s going to eat him alive.” I joke, smiling at the obvious excitement in Sally’s movements and the way she kisses his cheek as they walk.

“To think that was us, just a few weeks ago,” Andy remarks, slipping his arms around my waist and kissing me deeply. “We’re like an old couple now.” He quips and I give him a playful slap on the chest.

“If we’re still as close and fucking like we do when we’re old and grey, I’ll be more than happy.” I tell him as we turn and he starts to lead me back to our room.

“It’s a promise,” he says, smiling cheekily “I want to die with you riding my cock like there’s no tomorrow.”

“That can be arranged…” I reply, a mischievous smile on my face.

Once in the room, we realise how late it is and have a quickie before bed as Andy has to be up stupidly early for his shift (we both orgasm though, so I don’t mind) and cuddle up, drifting to sleep.

 

I stir, lifting my sleepy head and yawning as Andy dresses for work. He sees me awake and walks over to the bed, kissing me deeply.

“What are you doing up?” he jokes, stroking my cheek lovingly. “it’s only 5.30.”

“It’s not as comfortable in here without you,” I pat the bed, pouting. “Can’t you come back in? Even for 5 minutes…?”

“Don’t tempt me,” he replies with a grin, kissing the top of my head. “I’ve got to go or I’ll be late.”

“Have fu-un.” I singsong sarcastically, a little ill tempered as he heads to the door.

“Hey,” he turns back and points at me cheekily “Stay Sexy.”

I smile back at him, watching as he leaves. As soon as he closes the door I let out a long, tired groan and fall back onto the pillow, drifting back to sleep.

I meet Sally for breakfast, returning the Inquisition she gave me after the night Andy and I got together. Unlike her, I get all the details and I mean ALL. She tells me every position they used, how many orgasms (each), even his size and the fact that she allowed him to cum inside her completely unprotected, leading to her making an early trip to the labs to get a morning after pill. As you can imagine, the rumours about her and Josh didn’t take long to start and spread like wildfire, taking the onus off Andy and I, though one rumour did have us involved in a foursome in the institute’s pool after dark, which was quickly dispelled by the guard who was on duty the night it allegedly happened.

 

On his next morning off, Andy goes to see his mother and it doesn’t go well, she slams the door in his face as soon as he tells her his leaving date, giving him no opportunity to ask about meeting me. He writes her a letter and sends it the next day, receiving a response two days later. To say her letter was vile would be well wide of the mark. It was so vile, in fact, he was reluctant to show it to me, worried I wouldn’t be able to take his mother’s words. He was almost right.

To Summarise her long and ranting tirade, I was just an evil little bitch who only wanted to steal her precious baby boy from her, there was no point in meeting me as he would probably be killed in action, so we would then have nothing in common and if I couldn’t keep him here, safe, anything that happened would be my fault. She added a strange part at the end saying that it was a waste of time getting me pregnant, as far as she was concerned the child would be mine and not his. Neither of us could figure out where that came from as Andy had made no mention of having children in his letter.

 

We drew a line under it and decided to make the most of our remaining time before he had to leave, spending every possible second together. We went on dates, one of which was to the cinema to see the latest rom com, something Andy wasn’t a fan of but I gave him a blowjob in the back row in return for putting up with it.

In fact, the only time we spent apart, besides when he was working (though they made an exception on a few occasions), was when I had my period during the second week, and before you go slating him for not being able to put up with it, the problem wasn’t him. Andy was extremely understanding, getting me painkillers and hot water bottles to help my cramps and cuddling me or giving me space when I needed him to. The issue was me, no matter how hard I tried I couldn’t get comfortable at night, tossing and turning the whole time and keeping us both awake. It was OK for me, I didn’t really have much to do during the day so I could nap when I needed to but Andy, my poor Andy, had to work, pro plus and coffee can only help for so long. By the fourth night (it had started shortly after my cramps did), two days after I came on, he looked like a zombie and it was effecting his work, so I told him to sleep back in his old room until I was clear of it. He did so very reluctantly but understood why (Don’t worry, we more than made up for it afterwards).

The company held a leaving party for him in the dinning room on the evening before his last full day, partly so he had time to recover but also so he and I could spend our last 24 hours together alone. It was at the party that I finally decided what I was going to give him as a leaving present, besides the album of erotic and nude photos of me, that I had asked Sally to take and I secretly printed in the lab one quiet evening. I was going to let him fuck my ass, something I knew that Sally had already let Josh do, so I asked her for advice.

 

Surprisingly, Andy didn’t want to spend our last day together doing what I expected him to, which was basically fucking in bed. He wanted us to revisit the places where we had spent our most memorable dates, creating new memories of them for us to think about whilst we were apart.

“We’ve got all evening and night for that kind of fun,” he had said that morning with a smirk “besides, it’ll make the memory of it all the sweeter.”

So that’s what we did, heading to our favourite cafe, the cinema to watch the latest Marvel movie, where I gave him a handjob whilst he fingered me, out to some famous local hills where we were nearly caught fucking in the middle of a ring of bushes by someone walking their dog (if they had looked to see what was intriguing their pet so much rather than pulling it away by the lead the game would have been over). The only time we headed back to the institute before the evening was to get dressed up for a swanky dinner, him in his Tuxedo , me in the dress I had worn to Bridge’s party.

Finally back in our room we spend the next three hours making love, passionately and rough, aswell as slow and lovingly. We do it all over the room, in bed, in the shower and the bath, me bent over my dresser, stood against the wall, even leaning on the window, I could go on but I’ll spare your blushes.

It was after a particularly rigorous session in bed, as we recovered cuddling close, that Andy finally asks me about a new addition I’ve made today.

“So what’s with the butt plug?” he starts with a curious look “I mean, I get that it increases our pleasure but…”

I giggle mischievously, having taken the opportunity before this last session to slip into the bathroom, removing the plug I had had in most of the day and cleaning myself out with a douche before putting in a fresh one with a wider stem.

“I want to give you something really special to remember me by.” I tell him, stroking his chest as I gaze at him.

“More special than that photo album?” he grins widely “I’m going to have to find a good place to stash that in the barracks to stop the others seeing it.”

“You know how I lost my virginity…” I start, Andy immediately puts his finger to my mouth, stopping me, afraid that talking about my being raped might spark a memory in me.

“Don’t talk about that,” he says quietly “I don’t want you to traumatise yourself again bringing it up.”

I place my hand on his chest, reassuring him that I’m OK and continuing when he moves his finger.

“The one thing, thankfully, that he didn’t do was to take my other virginity…” I look at him with loving, confident eyes “I want you to take it from me…”

“Charley, what are you saying?”

I scoot up so our faces are level, taking his cheek in my hand and looking at him with sincerity.

“I want to give you my anal virginity. I want you to fuck me in my ass.”

“You do?” he’s taken aback, a little disbelieving.

“I do,” I tell him truthfully “I want to give you everything, my whole body is yours.”

He kisses me passionately, caressing my body hungrily “When do you…” he starts to ask.

“Right now,” I state confidently “that’s what the plug is for, to prepare me.”

He makes me promise that if it gets too painful that I’ll tell him to stop as he doesn’t want to hurt me, I agree even though I’m determined to do this. I get on all fours, facing the mirror for some reason and he gets behind me, examining the plug.

“So, how do I do this?” he asks, gripping the plug, preparing to pull it. “Will it hurt if I pull it out.”

“You pull, I’ll push. Just do it steadily, I’ll guide you.”

“Ok, ready?” I nod in response and he gingerly starts to pull as I push it out. It comes out quite easily, leaving my asshole slightly open. I tell him that there’s some lube in the bedside drawer and he retrieves it as I lean on my chest, reaching back and spreading my ass cheeks, keeping my tight hole open. He lubes his middle finger, sliding it in and gently stretching it, adding a second when I tell him and eventually a third, opening me nice and wide.

When I feel ready, I tell him to get his cock good and slick, then to put it in slowly. I feel him get behind me, pressing his cockhead to my opening, my heart hammering in my chest as the nervousness rises. I spread my cheeks wider, breathing steadily and deeply.

“I’m ready,” I tell him “do it.”

He starts to push forward, a little too gently making his first two attempts fail.

“You’ll have to go a bit harder.” I say.

“Are you sure?” I can hear the nervousness in his voice.

“Yes, it won’t go in otherwise.”

I breathe deeply as he tries again, pushing harder this time and I push with my ass muscles as Sally said it makes it easier. I wince as I feel his cockhead force my hole wider, working it’s way inside centimetre by centimetre. I grimace, feeling a little pain as it stretches me wider, I let out an anguished cry, making him stop.

“Keep going,” I tell him “I can take it.”

I see him nod in the mirror and feel him push a little harder, the widest part of the head almost in. I let go of my ass cheeks, moving my hands back by my head and clawing the bedsheet. With a pop the head slides in, the sudden loss of resistance making the first inch of his shaft follow it and I let out a loud gasp, gripping the sheet so tight that my knuckles turn white at the intrusion.

“You ok?” he asks, concern etched on his face in the mirror as he sees a tear run down my cheek “We can stop if you want.”

I shake my head “I just need a minute to adjust.” I tell him, letting out a long breath.

After a minute or two I nod at him and he starts to slowly inch his throbbing manhood further inside me, the strange feeling of my bowels being filled causing a lump in my throat, there’s still a little pain but it’s greatly diminished from what it was before. I pant, long and hard as his shaft slides deeper into my bowels. With a victorious grunt, his crotch touches my ass cheeks and he holds still, giving me time to get used to it.

“Okay,” I tell him a little breathlessly “you can start, babe.”

He starts to fuck me slowly, watching every expression on my face in the mirror to assess how I’m coping, gradually reaching a slow, steady rhythm. The pain fades as I grow used to the sensation and an eerie pleasurable feeling spreads from my asshole to my pussy and, finally, over my body. My squeals turn to moans, the pace steadily pushing me closer to orgasm.

“Fuck, your ass is so tight, babe.” He breathes, leaning down to kiss my shoulders. “can I go a little quicker?”

“Mmmmm please!” I gasp, clawing the sheet, this time in bliss.

He leans back and adds some more lube, starting to gradually thrust harder and faster. He doesn’t go mad but sets a fairly quick pace, his balls smacking against my pussy and adding to my pleasure. I groan long and gutturally, a twinge of pain every now and again, my orgasm building much faster now and I start to lose my mind a little.

“Fuck me! Take my ass! Own me! Oh fuck! Oh fuck! Ohhhhhhhhh fuuuuuuck!” I look back at him, pure lust in my eyes.

“Do it babe,” I growl “take me hard!” Pushing back to meet his thrusts.

He grabs my hips and pumps my ass hard, my screams and squeals spurring him on. My asshole starts to twitch around his cock, my release barrelling towards me.

“Yes! Yes! YES!” I squeal with each hard thrust, my pussy quivering as his balls smack it harder. I throw my head back and he takes the opportunity to grab my hair, using it for leverage as he fucks my tight hole mercilessly, adding more lube at regular intervals. He pistons his hard cock into me, any fear of pain gone as I tell him to fuck me harder and harder. I reach down and rubbing my clit as his shaft rams into my ass and his balls slap my pussy. Letting out a loud, deep groan that turns into a scream as I orgasm, my ass clenches around his shaft, forcing him to his own release. A slight nauseous feeling is quickly overcome by ecstasy as he fills my bowels with his thick semen, thrusting hard inside me and grunting in triumph.

Spent, he slowly pulls out of me and collapses onto the bed, breathing hard. I feel his spunk start to leak from my gaping asshole, a slightly painful but pleasurable throb emanating from it.

I crawl over to him, lying next to him and stroking his cheek as we recover.

“Fuck, Charlotte, “ he pants, finally able to speak “that was incredible! Thank you.”

I lean in and kiss him passionately.

“You are definitely doing that to me again before you leave.” I tell him between pants.

“You enjoyed it that much?” he grins triumphantly.

“Hell yeah! I’ve never felt anything like it.”

We kiss and caress each other for a while until we’ve recovered before heading to the shower. The original intent was just to clean up before sleeping but I can’t help letting him fuck my ass again under the warm water. Once clean and dried, we head to bed,  cuddling face to face, kissing until exhaustion overtakes us and we drift off.

 

In the morning I wake him with a blowjob, sucking him until he explodes in my throat then letting him lick me to two orgasms. We have a hard, passionate fuck in bed, ending only after he’s filled my pussy with two loads and I’ve orgasmed 6 times. He takes my ass again in the shower, my squeals of pleasure echoing around the walls as he pumps my ass full of his seed and makes me claw the tiles as a final orgasm pulses through me.

Though both of us want more, we have no time, we get dressed and head to our last breakfast together for just over for three months. After, we head to the train station, Sally and Josh joining us to give moral support. I hold on to him tightly as we wait for his train to arrive, his hand gently stroking my back as I fight to hold back my tears. His train pulls up to the platform and I give him one final long, loving kiss as my eyes start to well up. The train doors open and he grins at me, mischievously before sticking his face into my cleavage and ‘motorboating’ me (for those of you that don’t know it’s when someone puts their face between a woman’s breasts, and rocks their head rapidly from side to side while making a noise like a motorboat) making me giggle like a schoolgirl and giving me a brief reprieve from my sorrow.

As he grabs his suitcase and turns to enter the train I quickly swat his ass, making him turn back.

“See you soon, Big Boy.” I say, my voice quivering.

“Stay Sexy.” he replies with a smirk before stepping on and taking his seat. We wave and blow kisses to each other as the train pulls off and gathers speed, it disappears around a corner in the track and the dam inside me finally breaks. Sally wraps her arms around me in a hug and I sob uncontrollably into her shoulder.

 

To be continued…