You Can't Put Your Finger In There!

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Jeff gets in over his head with adventurous lover
2.4k words
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There's just something about goth chicks. I don't know what it is, but they do it for me. It could possibly that they scare me a little.

Kara was a barista, kind of. She worked at a coffee shop, but it wasn't a chain. The coffee wasn't that great, and I think her duties as a barista were to squirt the flavor syrups into the coffee.

She was slight with perky a-cups, but she when she spun around the coffee station, she would betray some deadly curves behind her apron. She had tattoo sleeves and enough piercings on her ears to add at least a pound to her head. She had short black hair and makeup reminiscent of death from Sandman: very dark eyeliner and a bloom surrounding her left eye.

Despite the bad coffee, I was hooked--all because of her, and drank at the shop at least twice anytime she was working, once I figured out her schedule. I would come in, order a coffee and watch her grudgingly make it for me. Then I would go sit in the corner and pretend to play with my phone or read the hip alt weekly paper stacked up at the entrance. I would be positioned to surreptitiously watch her work.

Despite never smiling and obviously hating her job and most if not all of the clientele, she had an accidental grace to her movements that was positively beguiling.

I could guess what she thought of me: probably some corporate suit wannabe yuppie kid, which was true in it's own right. Although I did work for a non-profit, I worked in the finance side, and spent most of the time working around IRS regulations. And I did wear a suit. This wasn't the career I set out to, but I was young, there weren't a lot of jobs available, and I was planning on figuring it all out after I paid off my immense student loan debt.

After about two months of creeping, I decided that it was time to sack up and ask her out. I rationalized that I had nothing to lose. In fact, if she said no, at least then I would be too embarrassed to come back and would save money by not having two cups of expensive but awful coffee day.

She worked the afternoon shift on Saturdays, and the coffee shop was conveniently right next to a dive bar. I went to the dive bar at noon for some liquid courage, and after two shots of shit whiskey, three tall beers, and a water to mask the beer, I got off the stool straightened up my clothes, and headed next door.

No one was in the shop when I came in, and Kara was working alone. She was in the back wiping a table. She looked up. I knew her name because she had to wear a name tag, which she had made herself and was artistic in some ornate calligraphy. She didn't know my name, but she knew me by my order.

"Medium coffee, right. I'll be right there."

"No thanks."

"What? You want something different? Like a mocha?"

"No. I was just wondering what you were doing tonight."

She froze, and I felt my face blaze up from fear and embarrassment.

"I have thing."

"Oh." I pressed on because there was no turning back. "How about tomorrow night?"

"Nothing."

"Let me take you out."

"It's a Sunday."

"We can go out on a Sunday."

"Okay."

"Great!" I smiled. I'll come by here after your shift. You're off at 3:30 right?"

"Creepy, but yeah. 3:30, but I'll want to get changed."

At this point, you've made the date, and you have to suavely extricate yourself from the room before you say something stupid. I failed.

I backed out the door with a stream of goodbyes like I couldn't choose one. "Great. See you then. Can't wait. Take care. See you tomorrow. It'll be fun. I'm Jeff by the way. Bye..."

Once out the door, I pretty much took off and ran.

***

The next day, I showed up at 3:15, and hung out outside the coffee shop until she came out.

Oh my God. She came out wearing a little black dress. Sexual plutonium. It contrasted with her stark milky skin and played with her black tattoos. She was a vision.

I smiled and tried to say something.

"Hi! You... look... uh... great."

"Thanks," she said flatly. I figured you only saw me with the black tee, black pants, and black apron, so I thought I probably shouldn't shock you with color. Not that I own any clothes with color."

I think that was a joke, but I was too scared to laugh.

"So where are we going?"

I knew I was down on points as far as charm was concerned. I had acted like an idiot and hadn't showed any personality. It was time to take risks and act boldly. I offered her my arm.

"Take hold! It's a surprise!"

After about fifteen minutes, I finally was able to relax a little and make conversation. I had assumed she was a vegetarian, so I had made and packed tofu miso sprout salads to eat. I led her to the canoe livery next to Baker Street Bridge on the Brine River that was right downtown next to Naragansett Park. My initial plan had been for a canoe ride, but I didn't dare bring it up with her wearing such a low-cut skirt.

So we ate the salads by the salads at a picnic table looking down at the river.

"How'd you know that I was a vegetarian?"

"Lucky guess?"

She smiled. Wow. It was the first smile I'd ever seen on her. It lit up the whole park. She had a great row of teeth and her eyes brightened.

"Whoa?"

"What?"

"I've never seen a smile before. Its beautiful."

"Shut up."

"No. I'm sorry. I meant, you are always so serious at the coffee shop."

"I fucking hate it there. I work there as a favor for my dad because he can't afford another employee."

I thought about offering advice on making better coffee might make the place more money, but I figured it would be better to move to another line of conversation.

Well, it's a very pretty smile. That' all. So, what do you do when you're not barista-ing?"

She was an art student at the Vermeer Institute, and I'd read that it was a highly regarded program internationally. She didn't have any career goals, and just knew that she loved art. She had waited four years before going to the institute, and felt awkward being older than most of the other students.

Once our salads were over, we went for a walk around the city. She took my hand, and I felt lighter than air. Eventually, she maneuvered us to her apartment.

"Well, this is me."

"Oh. Uh. OK. Well, I had a great time. Maybe we could do it again sometime."

"Yeah. That would be nice. I had a good time too."

We exchanged numbers. I went in for a polite hug and she drew me in for a kiss. It took me by surprise, but it was heaven.

"See you soon," she winked, and went up to to the door to her apartment.

I watched her get in, and turned away and headed off for the subway.

I was just two blocks away, when I felt a text.

It was Kara: "Come back here. Dates not over yet."

Just reading it gave me a tingle in my pants. I spun around and practically sprinted back to her apartment.

I got up to her door. Over the intercom, I heard "I'm up in 3B," and she buzzed me in.

I ran up the stairs to 3B, and before I could knock, the door opened and a hand grabbed me and yanked me in.

In seconds, she had me on the floor with her tongue down my throat. I tried to join in and clutched on to her ass. Underneath that spectacular dress, she had two perfect round cheeks and I held on to them for dear life.

She was straddling me, and was kissing all over my face, but it wasn't sloppy. She knew what she was doing. It was manic, but it was dangerously arousing and she was in control.

She lifted herself off of me for a second and raised her ass off my crotch, and looked down at me. "Wanna see a magic trick?"

"God, yes!"

She then grabbed the straps of her little black dress and in less than half a second had pulled it completely off and sent it flying.

She was completely naked! She hadn't been wearing anything underneath that thing!

"Oh my god!" I yelled.

She went back to kissing me, while simultaneously working of getting my belt and pants off. Her lips formed perfectly around my mouth, and her tongue explored all of my mouth and throat.

She was very deft, and my pants were soon off. She kissed me on the lips one more time and said, "I'll be right back."

She crawled down and pulled my boxers down and without using her hands completely deep-throated me. I took my shirt off while I enjoyed her work.

She had great suction and was a wonder with her tongue. She used her teeth a little bit down at the base, and I was surprised by how good the little shocks of pain felt.

As good as this all felt, I felt wrong not doing anything. I sat up and raised her head off my dick.

"Where's your bedroom?"

She nodded over at a door to the left of us. I took initiative, and pushed her back on her ass, grabbed her by her thighs, and picked her up. I carried her over to the room and threw her on the bed. She landed and got on all fours and gave me a hungry look. "On your back," she commanded.

I quickly complied with a leap to her bed. She climbed on top of me and went back to work on my dick with her pussy in my face. It was a picture. Her white skin and trimmed pitch black bush looked like an erotic black and white photograph. Her folds were so inviting, and she was sopping wet. I dove in with my mouth and felt her moan into my cock.

I lapped up her moistness like a dog, and judging by her writhing legs clamping onto my head and her continued moans, he was loving it. Meanwhile the hoovering she was doing on my dick was bringing me closer and closer.

I was so close to coming. Her taste, her scent and the view of her had brought me to the edge, and then it happened. Something was in my asshole!

I howled. I was not expecting this, and it had never happened before. I had always thought it disgusting, and out of jerk reaction, I wailed and flipped her off of me. Her teeth tracked their way off of my dick as she was yanked off, and it really hurt. Also, my erection was completely gone.

The terror soon subsided and I looked at her. I think I hurt her feelings. She looked hurt and maybe even close to tears.

"No. I'm sorry. I just wasn't expecting that. No one's ever done that before."

She looked up, "Really?" She was incredulous.

"Never."

She crawled back up to me and lay next to me on her side. "I don't think we hang out with the same people."

"Probably not, but I really like you."

"I like you too."

We laid there in silence for a while. She put her hand on my shoulder. "Will you trust me for a second?"

"Okay."

"Turn away from me."

I flipped over. She was now behind me.

She put her tongue in my ear and then whispered, "this is what I was trying to do."

She then placed her finger on the outside of my asshole and slowly pressed against it and massaged around it. At first, I didn't like it at all.

"I need you to relax," she whispered.

I took a deep breath and let it out. I laid there and tried to have an open mind. It took awhile, but I noticed that my dick was slowly coming back to life.

"There you go she whispered. Now lay on your belly."

I delicately laid on my belly being careful with my erection.

I felt her climb on me and then felt what was unmistakably a mouth and tongue around my anus. She licked the hole for a while, and it was actually starting to feel pretty good. Then she started probing inside my ass with her tongue.

I accidentally groaned.

"There you go," he said. She repositioned herself. "Stay relaxed now." I then felt her enter my ass with two fingers, and I clenched up again. "RELAX!" she commanded. I tried to comply.

She lifted up my top leg, and sat upright behind me and slowly inserted the fingers again. Her finger pads were pointed down and towards my dick, but her inside me, and she started massaging down in slow deep strokes. With her other hand, she grabbed my dick and slowly stroked it.

Her fingers inside my ass were pressing harder now, and I felt something building up.

"There you go. Relax and let it happen."

She pressed harder and harder and slowly massaged my insides and I just released. I came out of my dick, but it was nothing like orgasming from jerking off. It felt great and I felt so relaxed, like some kind of stress I had carried my whole life had finally been released. I moaned and moaned, and she crawled back up to me and just held me.

I didn't realize it for a second, but I was actually crying. I think it was the greatest orgasm I had ever had.

She pulled the covers over us and held me. I felt guilty about not getting her off, but I didn't know if I had the energy. I turned back towards her and tried to go down on her.

"No. It's okay. Just lie here and hold me."

Initially, I had thought we were going to have rough athletic and crazy sex, but even though we ended up stretching me beyond my comfort zone, it was one of the most intimate and meaningful sexual experiences I had ever had. It took a lot of trust to let her do that to me, and we became a lot closer by that experience.

Up to that point, sex was just a really fun activity I participated in, but Kara taught me that it can be so much more.

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5 Comments
AnonymousAnonymousabout 10 years ago
Well done!

Probably one of the most arousing stories on here - WRITE A PART TWO, PLEEEEEASE!

butterflygurlbutterflygurlover 10 years ago
part 2

I would love to see a part 2. Great story line and I love it.

Rawmaster50Rawmaster50over 10 years ago
Yeah this one needs a second chapter

Lol at the stunned ending of the story. Yes, we need more of this story. She obviously was prepared for sex and he was clueless. Being male, I have been there, established residence and have a post office box with a small apartment. It will be fun watching him grow and change

AnonymousAnonymousover 10 years ago
part2

Cant wait until she breaks out the toys in part 2.

rsqman68rsqman68over 10 years ago
Oh Hell Yes!!

A prostate massage is such an incredible rush.

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