Jealousy Ch. 02

Story Info
Nick's planned date takes an unexpected turn.
5.2k words
4.39
20.2k
37

Part 2 of the 2 part series

Updated 06/09/2023
Created 01/26/2019
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Thanks to everyone for the great response to the first chapter of 'Jealousy'. I really do appreciate the ratings and comments. This chapter continues from the first, and I have chosen the leave it in 'Incest/Taboo' on the account there are references to Sarah and also that this is the real crux of the story and you will see in future chapters.

I hope you all enjoy!

*****

Sarah had said little to me since she found out I was meeting her former close friend, Leah, for a date. She had gone to work in the morning without as much as a goodbye, but did have the grace to wish me luck as I stepped out of the door. I was all suited and booted, ready to go to a swanky restaurant where Leah and I had arranged to meet. Or rather where our mothers, who had organised this rendezvous, had arranged.

I checked my watch. She was over ten minutes late. The waitress was starting to eye me with suspicion and pity, as if he thought I had been stood up. I took little shame in eyeing her up back as I waited; I was a single man still after all, despite my mother's best efforts. She was a cute little red head (the waitress, not my mom), maybe a little older than me, with her hair up in what seemed an obligatory bun. The short, tight material of her black dress encased her ass perfectly, including a little dip between the cheeks, and the plunging neckline did little to hide the small, but pert, tits underneath. She saw him looking at her, and walked over.

"Can I help you, sir?" she asked politely.

"No, I'm fine thanks...," I started, searching for the name badge that she wasn't wearing (and ended up looking more like I was staring at her tits)- this was too upscale a place for that.

"Rosie," she finished. "Let me know if you need anything."

With that she walked away to do another job. Rosie seemed more pleased that I was checking her out, than disgusted, I noted.

Leah was nowhere to be seen, it was coming up on twenty minutes. I texted my mom to check everything was okay but received no reply, likely on account of it not being charged.

"Are you still expecting company, sir?" Rosie asked queried, who had seemingly appeared from nowhere.

"I was," I replied, staring at my watch once more. "But they are over thirty minutes late, I think I should take that as a sign."

"Well, whoever stood you up must be an idiot," she blurted. "...sir."

"Well thank you," I blushed.

"Can I get you the check, sir?" she asked.

"Please, call me Nick. The check would be great," I said, before calling her back as she turned away. "And your number would be fantastic."

Rosie smiled, and walked to the register to print my receipt. Two minutes later, the check for my solitary drink was on the table along with a phone number scribbled on the bottom, a cute heart and a note saying she gets off at midnight (if I had my way she would certainly be getting off at midnight). I pocketed it, and smiled to myself. That was the first number I had gotten since Emily. Standing, I put my overcoat on over my suit and headed to the door. The doorman (yes, it was that kind of place) cleared my path to the outside world by opening the door, and I turned to him to give him a quick nod. As I turned my head back, all I saw was blonde hair flying at me and tits smothering me. I staggered back, but managed to maintain my balance.

"Watch where you're going!" I admonished, before looking up and falling speechless. A vision of absolutely beauty stood before me. Her aforementioned long, blonde fair flowed down to her midriff; she wore it down, and had curled it into waves. She was wearing a full-length gown, that was sheer white and fairly tight- tight enough to show every curve on her clearly sexy as fuck body. She was of medium height, perhaps up to my chin and everything about her looked toned. Of course, I would have to get the beautiful dress off her, just to double check. There was one area, however, that I didn't need to wait to check: her tits. The design meant that the neckline plunged down to the bottom of her cleavage, revealing enough to get me semi-hard. They weren't the biggest in the world (maybe a C cup?), but they were round, and did not sag one bit even without a bra. I didn't know who this girl was, but screw my date, I was going to get her naked if it was the last thing I did.

"Nick?" she asked.

"Do I know you?"

"It's Leah, Leah Benson? I'm so sorry I'm late!"

"Shit! You've grown up!" I exclaimed, taking another look at her.

"I could say the same about you," Leah replied, giving me the once over. It was only then I realised how long it was since we last met. We mustn't have been older than 14 or 15. Our families had drifted away from each other in the previous few years, and it was now just our mothers who met up albeit irregularly. "I'm so sorry I was late, I couldn't make my mind up about my outfit then I dropped the curling iron and the taxi was late..."

"It's okay," I reassured, before laughing. "We've skipped ahead anyway, I've already motorboated you!"

"Yeah, sorry about that, I came around that corner like Usain Bolt!" Leah said, making them both laugh. "I take it our table has been taken?"

"Yeah."

"I know this nice cocktail bar a couple of blocks over, where we wouldn't look like twats in our outfits. We could grab a drink, catch up?"

"Thank you, I hate it in that restaurant. Not my scene."

"Mine neither, come on."

And with that, she turned and hailed a cab. Well, I assume that's what she was doing. I didn't know, because I was in a trance. As she turned, her ass was revealed. Her perfectly shaped, very round, toned ass. It was big, but not obscenely so, big enough to make it a handful to grab, but not impossible. It was shaped like a peach (cliché, I know), had no droop whatsoever, and it was glorious. The bounce it had, as she turned to search the street, was all it took to make me rock hard. Luckily my overcoat would cover it.

"Keep looking," Leah said out of nowhere, while still looking away from me. "I've worked hard enough on it, attention is welcome."

That made my hard on even worse. She was sexy and she knew it- a deadly combination. Eventually, a taxi stopped. Ever the gentleman, I opened the door and let her slip inside which earnt me a genuine smile (chivalry isn't dead, people). I noticed that she wasn't wearing heels which I thought she might be, considering her dress.

"No heels?" I queried.

"Good spot, Sherlock," she laughed. "I don't like them, they're not comfy, so I don't wear them."

The matter-of-factness of it all just made me even more attracted to her. A girl who knew her own mind, and did not compromise on her views even with the pressure of societal norms. I think I was in love.

We reached the cocktail bar, and she took my arm as we stepped inside and found a table. After three rounds of drinks we started getting tipsy. We had talked about everything, from the 'olden days' of us hanging as children to now. She even revealed she had a little crush on me when we were younger. After another drink, she confessed that she had masturbated to the thought of me fucking her before.

"That can be made a reality, you know," I winked.

"Not on the first date it can't," she replied.

"Why dress like that then," I scoffed, a little disappointed.

"Men! Firstly, I dressed like this because I think I look good in it and it makes me feel confident not to impress a man," she began, indicating me, and I prepared for a passionate rant. "But also, because I wanted to give you a sneak preview of what you might be in for..."

That comment alone was enough to make me go weak at the knees. Two more drinks later, Leah announced she had to go. She had an early appointment with a client in the morning, and needed to sleep; it transpired that she was a personal trainer, during the course of conversation, somehow making her even more attractive to me (I had a weird gym clothes fetish, don't ask.)

They settled their tab, put their coats on and grabbed another taxi. In the back, they were very touchy feely, his arm around her shoulders and her hand on his thigh. When they arrived at Leah's family's mansion of a house, he jumped out with her and told the cab to wait. He walked her to the door, and she fiddled for her keys.

"Shall I tell the cab to go?" I asked gently.

"Yeah, with you in it, to your home," Leah giggled.

"You're not going to invite me in?"

"No because I know if I do, I will end up letting you fuck me because I am incredibly attracted to you. Maybe it is the history we have as friends, or the fact you're just hot as fuck but this is the first time in forever that I have wanted to screw a boy and date him."

"Well let's do both then," I said, smugly. I felt the same way, but right then I was thinking with nothing but my cock, which had been hard since the moment we met- literally. I needed a release.

"No, because as soon as we fuck the sexual tension goes away and that makes the dating part harder, for me at least," she explained. "Are you free on Saturday? Only, it's my birthday party, and I would love you to be there."

"I'm already coming," I laughed.

"You are?"

"Yeah, your mom insisted all of us come: mom, dad, me and Sarah. I think it has something to do with the whole you and me thing."

"Well, great! A group of my friends are going out after the whole 'adult' bit, if you fancy it?"

"I'm in."

With a satisfied smile she turned to the door and tried to slide the key in, but I grabbed her arm and spun her back to face me. I grabbed her waist, pulled her in to my body, and pressed my lips against hers. It was not long before we were making out, our tongues jousting and hands roaming. After what seemed like an acceptable wait, I grabbed her ass. It was like touching a piece of heaven. Firm, but with a degree of softness. Toned, but not without jiggle. No sag, high up her legs and round as an apple. Not that I would ever let Sarah know, who prided herself on that area of her body, but this was the best ass I had ever handled. I let both hands grab, caress and explore as our make out session continued; it was only stopped by the hoot of the taxi driver's car. We giggled and pulled away.

"Still not going to invite me in?" I grinned. "Is a blowjob even sex? Handjob? Staring at you as I jerk off?"

"Goodnight Nick," Leah declared in a serious tone, despite smiling at my joke. During all the excitement she had dropped her keys, and bent over at the waist to pick them up. I gave her a quick slap, which gained a surprised laugh from Leah, and I skipped off down the path.

"See you Saturday," I called, as I jumped into the taxi.

The driver turned around to speak to me, "Sorry dude, wife wants me home on time tonight. You're my last fare. She is one hot piece of ass though!"

"Literally," I said, we both laughed. I gave her one last look as we pulled off, and she gave me a sexy wave. I was so horny it was unbelievable, that kiss had taken me over the edge. I still needed a release and Sarah was currently out of bounds. My hand wouldn't do it. So, when the taxi driver asked me where to, I gave him a location without thinking. Then I pulled out my phone and sent a single text.

*

"I'm glad you text," Rosie said.

"Oh really?" I said.

"Yeah, a night in with a sexy guy beats one alone," she said. "Especially when you're as horny as I am."

"You're very forward," I laughed, to which her response was pointing at her ginger locks.

"Anyway, seems you're just as horny as me," Rosie giggled, nodding at my crotch. I was still fairly hard, it was like Leah was some kind of natural Viagra. "Where have you been for the past four hours anyway? Fucking that girl that stood you up? In fact, don't answer I don't want to know. I'm so horny, I don't really care."

So, we walked in a mix of silence and generic small talk until we reached her apartment. She told me she was eighteen, and lived alone in an apartment her dad paid for as she pursued her dream to become an actress (welcome to LA, everyone). I sat down on her couch and she poured a drink for each of us, not that I needed anymore but I sipped it politely.

"I'm just going to go and freshen up," she announced and headed off into her bedroom. I watched her ass as it sashayed its way into the bedroom, it was cute- I wanted to destroy it. It had been years since I had been this horny, which made sense as I effectively had sex on tap at home. Well, I did, just not right now; I knew how it would play if I went home like this:

"Sis, your sexy as fuck ex-friend got me all turned on and refused to have sex with me. I really need to cum. Do you mind?"

I would have been slapped so hard I would have been bruised for a week. So, on account of my options being limited (by effectively being held as a sex hostage by my sister for so long), I had texted Rosie- not a bad option, in fairness. She was the first redhead I had been with, so I hoped she lived up to the hype.

Ten minutes later, when Rosie returned it was as if she had morphed into a different person. Her fiery, ginger hair had been released from the bun and now fell freely down to her just above tits. She had touched up her makeup, including swapping her nude lip for a shade of red that matched her new outfit; at least, what there was of it. Rosie was wearing a pair of red, lace panties, that I assumed was a g-string on account of it not covering much. The rest of her body was draped in a short, black, silk kimono that was struggling to contain her tits and slender legs. It just about hid the nipple but everything else was on show. She wore nothing on her feet, which was somehow sexier than wearing something like heels would have been.

This was the look of either a girl who was very confident about her body, or was so desperate to get laid properly that she could not wait for any more clothing to be removed than necessary. Not that I minded, I was of the same thinking. Either way, she knew how to get a man interested. I strode over to her, and shoved her roughly up against the wall. Even that earned a moan from her.

"How do you like it?" I asked, having never really fucked a stranger.

"I want you to control me, like this, to be aggressive and be adventurous," Rosie told me, as I pinned her up against the wall. "I don't like it especially rough, slapping, hair pulling and biting and all that- it doesn't do it for me. If I'm honest, I haven't had an orgasm that wasn't using my own hand in about 3 months so I'm sure anything you do will be fine." (I would later find out people with red hair are more sensitive to pain, and bruise like a peach. You learn something new every day).

I took the 'I'm sure anything you do will be fine' comment as gospel, and got to work. After a minute or two of making out, with a few neck kisses chucked in, I picked her up and physically threw her on to the bed. Rosie was on her back her kimono still on but open, and splayed across the bed. All that stood between me and her pussy, was those barely there panties. In one swift movement, in removed them and buried my head between her gorgeous, perfect legs. She had the most pubic hair of any girl I had been with (which admittedly stood at the grand total of 2), and I liked it; Rosie had trimmed it into a triangle that stood away from the creases of her legs and let me tell you, the curtains certainly matched the drapes.

After a few kisses of her inner thighs, I started to turn my attention to her clit. My thought process was if I waited a little while and made her orgasm first, it wouldn't be quite as embarrassing when it took me half a minute (thanks to Leah, and my now seemingly permanent erections). I started off with a few light breaths, before circling it with my tongue. Apart from an appreciative gasp when I started, I got nothing. When I started licking her clit itself. Nothing. Long St. Bernard-like licks up the whole of her vagina. Nothing. All of my best moves, and nothing. Apparently, anything I did wouldn't be fine. At least my failure had managed to make my erection disappear.

Then I realised; everything I knew, came from Sarah. Everything she taught me was geared to what she knew and liked (fuck you, sis). Even with Emily it was okay, she was a virgin too and we worked out what each other was in to as we went along and she was not dissimilar in what she liked to Sarah; foolishly, I thought Rosie would be the same without thinking. It only took another two minutes of me trying to mix it up, and a few pity moans to get my head pulled up (much like a comedian dying at a comedy club- I'm surprised she didn't boo).

"Let's try something else," she offered, and my face must have gone a deeper shade of red than her hair. "Guys always struggle to get me off orally anyway; girls on the other hand..."

"You're bi?" I asked eagerly, my limp cock starting to grow again. Why I was so excited I'm not too sure, Sarah was bi too- it shouldn't have been that big of a deal to me.

"You could say that," she smiled, wryly. "I mean I don't want to date another girl, but I don't mind fucking them."

My erection was back.

"So, what did you want to try instead?"

"I want you inside me, to fill me up."

"Okay, let me just get a condom from my wall-"

"You don't need a condom for where you're going," she said huskily, reaching into her bedside draw and pulling out a bottle labelled: 'Anal Lube'.

My cock twitched in a mix of nervousness and excitement. My history with anal sex was not an accomplished one (I had fucking Emily doggy style too excitedly, slipped out and ended up inside her ass on the thrust in. She wasn't very receptive to the idea after that.). Sarah swore against it, so I had never had time to practice and now it seemed as if I was about to be thrown in at the deep end (literally.).

"Have you done anal before?" Rosie asked.

"Yeah, course," I replied, which technically wasn't a lie (if the head's in it counts, guys).

"Well I'm tiny, like I mean I only come up to your chest, so you're going to have to take your time to start with and be careful," she warned, before laughing. "Especially if you're cock is anything over three inches. In fact, how big are you?"

She sat next to me on the edge of the bed and grabbed my cock in her left hand. She gave it a few strokes, causing a few drops of precum to ooze out.

"Holy shit," Rosie whispered.

"Acceptable?" I laughed.

"It's massive!"

"You think?"

"Yeah, it'll rip me in half! How big is it?"

"What do you mean?"

"Like how long is it, in length?"

"You know, I've never got a tape measure out and made a note," I said sarcastically.

"Fuck off, every guy has done that."

"Not me, every girl I've been with has been happy with it so I never felt the need."

With that Rosie jumped up and went into the kitchen and returned with a ruler. After a few more strokes to make sure I was fully hard, she pressed the ruler into my pubic bone and lined it up with the tip.

"Well," I asked, to break the nervous silence.

"It's a little over seven inches," Rosie said quietly.

"Is that good or?"

"Well put it this way, you're bigger than like 90% of guys."

Rosie, still wearing her robe, pulled the sash that tied it together out and wrapped it around my cock then measured it.

"And, you're 6 inches in girth which is insane, too," Rosie told me. "And if you ask me, more important than length."

"So..." I began wondering where my medical examination was going next.

"So, I need your cock in my pussy right now," Rosie declared. Hearing her talk so dirtily was not helping my horniness. "We're going to have to leave anal for now, save it for next time; I need to prepare myself for that."

She nodded at my cock, which swelled with pride, before I registered what she said.

12